My children live a short drive from my house.

I haven't seen them for more than a year.

When I go shopping, I sometimes choose a route that avoids their school. I've learnt to avoid certain places at certain times because there's always the possibility of seeing them. And, worse still, the possibility of them seeing me and walking straight past.

That's how I've been living.

Last weekend, I flew into Manchester, and something happened that I hadn't experienced in a very long time.

I felt alive.

And I've made a decision.

I'm leaving Cork. I'm moving to Manchester.

Now, for anybody who knows where I grew up, this is going to require some explaining.

Behind the Iron Curtain

Let's go back to 1986.

I'm 17 years old, doing my A-levels, living in Skelmersdale, and heavily into alternative music. I've got a little quiff, some spectacularly questionable fashion choices, and an almost religious devotion to The Smiths.

For those unfamiliar with Skelmersdale, it's a Lancashire new town between Liverpool and Manchester. Geographically, we're caught between the two cities, although culturally we're very firmly on the Scouse side.

This matters.

When I later lived in London, people seemed to assume that everybody from the northwest of England got along famously.

"Oh, no, no, no," I'd explain. "You don't understand. The northwest of England is basically the Cold War."

The M6 motorway was our Iron Curtain.

To the east, you had Mother Russia: Manchester, the Soviet Union itself, surrounded by its loyal satellite states of Bolton, Rochdale, Stockport and Oldham.

To the west, you had the United States of Liverpool, with its own collection of allied nations: Kirkby, St Helens, and the glorious independent republic of Skelmersdale.

We were practically West Berlin. A little outpost of Western civilisation, uncomfortably close to Soviet territory.

Although admittedly with considerably more roundabouts and fewer Soviet spies.

Crossing the M6 was no small matter. You were entering enemy territory.

And yet, at 17, I was regularly making the journey.

Manchester was our Mecca.

Getting there, however, was a complete bloody expedition.

Skelmersdale, in one of the great triumphs of British town planning, had been built without anybody having the brains to put a railway station in it.

So my friends Jamie, Justin and I would walk miles to the nearest station, catch a train to Wigan, and then another into Manchester.

We'd travel through Salford, home of the famous photograph of The Smiths standing outside Salford Lads Club.

That photograph, used on the inside sleeve of The Queen Is Dead, was iconic to us.

Forty years later, it still hangs, framed, on the wall of my office.

Funny how some things never leave you.

We'd eventually arrive in Manchester and make our way to Afflecks Palace, a wonderful collection of independent stalls selling vintage clothes, records, jewellery and all sorts of peculiar shit.

We'd spend hours agonising over genuine vintage Levi's 501s, suede jackets and whatever else we could find.

I was desperately trying to look like James Dean crossed with some sort of tortured poet, while my friend Justin looked suspiciously as though he was about to burst into a rendition of All Right Now and join Free.

Between us, we thought we were the coolest bastards in Manchester.

In reality, we were three lads from Skelmersdale who'd walked four miles to buy someone else's trousers.

But I loved Manchester. Despite being raised firmly on the American side of the Iron Curtain, I was probably already under suspicion of Soviet sympathies.

And forty years later, it appears I'm about to become a full-blown defector.

How I ended up in Cork

Before all of that, however, there's the small matter of how I ended up in Ireland.

My then wife and I had spent roughly fourteen years living in East Dulwich, a rather lovely, rather poncy corner of South London where every Victorian house had acquired identical bifold doors, a Scandinavian kitchen and an enormous mortgage.

Everybody smiled enthusiastically about how wonderful life was while privately shitting themselves that their City bonus might not arrive.

I rather liked it, actually.

But in 2020, we decided to move to Ireland.

My wife was Irish, and she'd been increasingly encouraged towards leadership positions in teaching. She wasn't particularly enthusiastic about becoming a headteacher in England, where the job seemed to involve being relentlessly battered by inspections, government targets and an endless succession of educational initiatives.

Ireland offered a different opportunity.

We'd spent fourteen years in my country. It seemed fair enough to spend the next chapter in hers.

Dublin was out. The housing market was completely bonkers, and I had no desire to spend a London-sized fortune on a powder-blue pebble-dashed house with electrical cables dangling down the side.

So we chose Cork.

A smaller city, more affordable housing, and what seemed like a lovely place to raise our family.

And for a while, it was.

We arrived in 2020, just as COVID was turning the world upside down.

There were financial setbacks, the usual complications of family life, and eventually the biggest change of my entire existence.

I came out as transgender.

I began transitioning.

And my old life fell apart.

Living like a ghost

I've written extensively about my transition elsewhere, so I'm not going to tell the entire story again.

But the consequences were catastrophic.

My marriage ended. I lost my family home. My relationships with my children broke down. My siblings stopped speaking to me. My nieces and nephews disappeared from my life, and almost every friend I'd ever had vanished.

Only my mother remained, along with two friends.

I found myself living alone in Cork, in a city I'd moved to for a family life that no longer existed.

And I stayed.

I stayed because of hope.

Hope that things would improve. Hope that my children would eventually want to see me. Hope that time might soften whatever anger or hurt had driven everybody away.

Hope that, eventually, something resembling normality might return.

People encouraged me.

"Don't give up, Stevie."

"Keep trying."

"Give them time."

All perfectly reasonable advice, of course. Nobody wants to tell somebody who's estranged from their children to stop hoping.

But I've discovered something over the last year.

Hope can become a prison.

It's difficult to describe the agony of living so close to your children and having absolutely no relationship with them.

They're getting older. Having birthdays. Making friends. Going to school. Experiencing all the ordinary things that make up childhood.

And I'm not part of any of it.

I'm not even somebody who occasionally drops in.

I'm a ghost.

And the worst part isn't some enormous dramatic event. It's the accumulation of tiny, ordinary moments.

Deciding which way to drive to Tesco.

Wondering whether you'll accidentally encounter somebody from your old life.

Knowing that your children are somewhere nearby, getting on with their lives, and that you're effectively invisible to them.

Then you go home, wake up the next morning and do it all again.

I've spent more than a year living like that.

And the really terrible thing is that nothing changes.

You can wait another week, another month, another Christmas, another birthday, and there's absolutely no guarantee that anything will be different.

You just get a little older.

And a little sadder.

I watched Will & Harper, the documentary about Will Ferrell and his transgender friend Harper Steele, and saw the warmth and acceptance surrounding her. I've encountered plenty of other stories where relationships have survived transitions, even if marriages haven't.

I never imagined I'd end up at the opposite extreme.

Scorched earth.

Almost everybody gone.

I sometimes wonder whether being so public about my transition made matters worse.

I didn't quietly disappear, transition in private, and emerge somewhere else hoping nobody would notice.

Quite the opposite.

I started writing Fast Track Femme. I went onto Instagram. I posted on Reddit. I talked openly about my experiences, my surgeries, my mistakes, my happiness and the occasional spectacular bit of stupidity.

Perhaps some people from my old life would have preferred me to disappear quietly.

Perhaps a less visible Stevie would have been easier to accept.

I genuinely don't know.

But I do know that I'm not ashamed of who I am.

I'm actually rather proud of her.

And I'm not going to apologise for building a life that I'm beginning to enjoy.

The decision

Recently, I asked my children what they thought about me moving away.

One replied that I should go.

The other two didn't reply.

And that, I think, was when something finally shifted.

I realised that I'd been organising my entire existence around the possibility of reconciliation.

I'd stayed in Cork because I thought that, somehow, remaining geographically close would make a difference.

That if I were just patient enough, understanding enough, persistent enough, eventually something would change.

But nobody had promised me that.

Nobody had said that another six months, another year, or another five years would make any difference whatsoever.

I was simply waiting.

And waiting was becoming my entire life.

I've had people tell me that moving away means giving up. That I should keep trying, keep hoping, keep myself available.

But there's a distinction I've finally come to understand.

Accepting something isn't the same as approving of it.

I don't approve of being estranged from my children. I don't think it's fair, and I would change it tomorrow if I could.

But I can't.

I cannot make people want a relationship with me, however desperately I might want one with them.

That's the reality.

And accepting that reality has been extraordinarily painful.

Because what do you do when the thing you want more than anything else in the world is something you have absolutely no power to bring about?

For a long time, my answer was to wait.

And it was killing me.

Not dramatically. Not all at once. Just slowly, through the endless repetition of ordinary days in which nothing changed.

But something has changed now.

Me.

I've realised that I can love my children, leave the door open, and still get on with my life.

Those things aren't mutually exclusive.

I don't have to stand in the doorway for the rest of my life waiting for somebody to walk through it.

And at 58, I'm becoming increasingly conscious that I don't have an infinite number of years left to spend doing precisely that.

That isn't bitterness.

It's arithmetic.

Manchester, forty years later

Which brings me back to Manchester.

The weekend before visiting my mother, I'd flown into Manchester on my way to Leeds for a night out.

I spent time wandering around the city, looking at how much it had changed since those teenage trips to Afflecks Palace.

Christ, what a transformation.

The old industrial buildings, the redeveloped waterfronts, the restaurants, the bars, the apartments. The sheer energy of the place.

It felt exciting.

And something else happened.

During my time in Leeds, six people came up to me and recognised me.

"You're Stevie, aren't you?"

"I follow you on Instagram!"

"I read Fast Track Femme!"

Six people.

It was surreal.

Here was a woman who'd spent much of the previous year feeling completely invisible in Cork, suddenly being recognised by strangers in northern England.

And the wonderful thing was that these people didn't know me as somebody's former husband, an estranged parent, or the person whose transition had caused an enormous family upheaval.

They knew me as Stevie.

Just Stevie.

And they seemed genuinely pleased to meet her.

Then there were the dating apps.

Oh, my God.

Within moments of arriving in Manchester, my phone started pinging.

Like. Like. Like. Like.

Attractive women. Interesting women. Women who seemed perfectly happy with the fact that I was transgender.

And I found myself thinking, What the actual fuck am I still doing in Cork?

Now, I'm not suggesting that the solution to profound family estrangement is a few attractive women on a dating app.

Although, frankly, it doesn't hurt.

But it reminded me of something I'd almost forgotten.

There's an entire world out there.

People I've never met. Friends I haven't made. Women I haven't dated. Places I haven't visited. Experiences I haven't had.

And I've spent so long mourning the people who've left my life that I've barely allowed myself to think about the people who might yet enter it.

Manchester made me remember what it felt like to look forward to something.

Not another attempt at reconciliation. Not another message that might go unanswered.

Something for me.

And I liked that feeling.

A lot.

A three-bedroom apartment and a very small dog

So I've been looking at apartments in Manchester.

And, good grief, the difference between what I can find there and what I've been looking at in Cork is astonishing.

I've been eyeing up some gorgeous three-bedroom riverside apartments, with enormous balconies, lovely views and enough space for all my ridiculous possessions.

A proper office. A home gym. All the artwork I've spent years collecting.

And, naturally, suitable accommodation for Colonel Chesterton, who will undoubtedly regard the whole place as his personal estate.

I can picture it.

My music playing. Friends coming round. Going out for dinner. Meeting people. Building a social life.

Perhaps even falling in love again.

It's a lovely thing to be able to imagine.

So, forty years after those teenage expeditions, I'm crossing the Iron Curtain again.

I'm moving to Manchester.

Shame.

It's a big, big word in our world. It's the backdrop that most of us live with, at least if you're my age. If you're 22 and started hormones at fifteen, this may not land the same way. For most of us my age, it does. I didn't start young. Nor did most of us.

I grew up in a tough, northern, working-class town in Britain. I was brought up in a one-parent family on benefits, and at one point the town had the highest unemployment rate in the UK. This was not the kind of place where you came skipping up the road in your mum's tights and stilettos.

Oh dear God, no, no, no.

You learned fairly quickly what you were allowed to be. And what you absolutely were not.

And so there was shame.

I want to be honest with you as I start writing this. I've had it in my head for a long time that I wanted to write an article called Shame, but I've never been entirely sure what the article actually was. Normally when I write something, I have at least a vague idea where I'm going. With this one, there isn't. So I'm going to try to work it out while I write it.

When I started my transition, I had three rules.

Actually, that isn't quite true. This was before I knew I was starting a transition. It was when I knew something had broken. The dam had gone. I could sense it falling away after twenty years, and I wrote down three rules.

The first was no shame.

That one mattered enormously, because shame had done some hideous things to me before. Hideous things.

There was so much self-hatred in my twenties.

Between about twenty and twenty-seven, I wanted desperately to be a girl. I don't say that lightly. I wanted it so badly that I tried to mutilate myself, to remove the thing I thought was standing in the way.

I couldn't bear the pain of it, so I went looking for ways to hide from it. Three-day benders on ecstasy and speed. The idea was simple: get high enough and, for a while, I might forget I was a man.

Then I would come round, and the shame was enormous.

This was never fetishistic for me. I wanted to be girly. That was it. And the pattern went on for years.

Eventually I quit Stevie. But I quit her out of shame. I was so ashamed of what I'd been, and so upset with the whole thing, that I piled on weight. I went from about 150 pounds to 300.

I've never written that number down before. I always say 280. That's a lie. It was 300.

Then, slowly, somewhere between thirty-four and thirty-six, I started to come out of it. It was endurance sport that really saved me. I'm not going to rewrite my own history to make this article work, but by about 2006 or 2007 I don't think I felt very much shame about it anymore. That roughly coincided with meeting someone and getting married. And, to be honest, I think I made a good enough job of being a husband that in some strange way I forgave myself for what had happened before.

By thirty-five or thirty-six, I was pretty much convinced I was cured. That was genuinely how I thought about it.

Cured.

There were leakages. Not just the sort where I could excuse myself for looking at transgender Reddit groups late at night. There were stranger ones. I would occasionally wake up in the middle of the night having dreamed that I was a woman. Sometimes I would be making love to some nebulous creature in the dream, but I was a woman while I was doing it. And I would wake up and the inevitable physical thing would have happened.

That did bring shame. It was a warning light.

Oh fuck. Be careful. You're not 100 per cent cured.

Don't prod it. Don't wake the thing up again.

And for years, largely, I didn't.

Then it woke up.

When that happened, my three rules were simple. No shame. No subterfuge. And do one thing. If that feels right, do another thing. That was it. No grand transition plan. No five-year strategy. Do one thing. See how it feels. Then do another.

That system lasted approximately two months, after which I looked at the accumulating evidence and thought:

Fucking Christ. I'm all in, aren't I?

Apparently I was.

The no-subterfuge rule lasted slightly longer. About four months. Eventually I burst. I have to tell her. I have to tell her everything.

But the first rule never changed.

No shame.

And this is where I have always got stuck when I've tried to write this article. I knew exactly why I had made that rule. I knew what shame had done to me before. What I couldn't understand was why it worked. Why wasn't I ashamed this time? Why didn't I feel the same terror? There must have been a point. There must have been a moment.

One day, after twenty years of supposedly being cured, I went onto the Next website and ordered a dress. I guessed I was a size 16. Turns out I was a 14.

Damn.

Can't wear the bloody dress now anyway. Don't like it.

But forget the dress. What did I feel while I was ordering it? That is the question I cannot seem to answer, because something else came roaring back almost immediately, and that I remember extremely well.

Secrecy.

Oh fuck. I'm going to have to intercept every parcel before it gets into this house.

There were only two or three parcels at the beginning, but instantly I knew the routine. Where am I going to hide this? Where can things go that nobody else will look? It was horribly familiar. It was the rhythm I had lived with for years in the 1990s.

I remember sitting in my office and looking around the room for hiding places. There was a little separate kitchen attached to my office, apart from the main kitchen in the house, and I actually started looking at the baseboards. Could I take those off? Could I get half-inch-thick things underneath there? And I remember thinking:

Oh dear God. Here we go again.

What disturbed me was how easy it was, how naturally I slipped back into deceit. Twenty years had passed and apparently my brain still had the entire operating manual.

But thinking about it now, I'm not sure what I felt was shame. I think it was guilt. There is a difference.

I felt horribly guilty about deceiving my wife. I didn't want to intercept parcels or hide things. I didn't want to become that person again, moving objects around the house and maintaining a secret parallel existence. And for those months when she didn't know, the guilt was enormous.

But was I ashamed of wanting the dress? Was I ashamed of Stevie? I don't think I was.

Guilt says: I've done something wrong.

Shame says: There is something wrong with me.

Those are not the same thing.

I remember some of those very early days. I remember sitting watching Taskmaster with my children in the evening, knowing perfectly well what I had been doing that afternoon. I had scrubbed the makeup off so hard that my bloody eyeballs hurt, and now I was sitting there as Dad as though nothing had happened. There was definitely an uncomfortable feeling attached to that. But again, when I examine it properly, I think it was guilt. I was hiding something my wife didn't know about, moving between two worlds and pretending one of them didn't exist. That felt wrong. But was I ashamed that I had spent the afternoon as Stevie? I honestly don't know that I was.

And perhaps somewhere along the line I had managed to pull guilt and shame apart.

But that still leaves the question. Why? Why had the shame gone?

The world had changed. There were about six trans women around my own age whose profiles I saved. I would literally have their pictures open on my monitors and look at them. Not because I fancied them. I was studying the evidence. Could this work? Could I do this? One worked in what looked like high-end finance. Another had been a Marine. They had jobs and lives. They seemed to function perfectly well. They had transitioned, and then gone to work.

That sounds hilariously mundane. Maybe that was precisely why it mattered.

But even that doesn't entirely explain it.

So I'm stuck. And I'm going to do something slightly unconventional.

When I'm trying to understand something about myself and I keep circling the same memories, I sometimes get a frontier language model to interview me. I give it the problem and ask it to interrogate me one question at a time. Sometimes it has been surprisingly useful. Sometimes it produces complete bollocks.

But I genuinely don't know why the shame disappeared. So rather than invent an answer because this is an essay and essays are apparently supposed to have answers, I decided to try the interview.

This is what happened.

Interview

Take yourself back to just before you ordered that first dress. What did you believe was going to happen? Were you thinking about transition, or was there almost no internal negotiation at all?

I think I remember. I really just wanted the dress.

There was something quite specific in the background, though. Throughout my marriage, I had almost never tried on any of Liz's clothes. There was one exception, a beautiful Ted Baker dress sometime around 2016. I tried it on once, realised there was absolutely no chance it was going to fit me, and that was that. I never really did it again.

I think that mattered to me. There was something about buying my own dress that felt more honourable. I wasn't stealing my wife's things or sneaking around in her wardrobe. It was mine. I had chosen it and paid for it. I could tell myself: it's just one dress. How much harm can one dress possibly do?

I certainly wasn't thinking that I was transitioning. It was much simpler than that. I just thought: I really think I'll feel nice if I do this. I think it will feel right. Maybe underneath that I simply wanted to explore the feeling a little bit and see what happened.

When you thought, "I think it will feel right," what did right actually mean? What were you hoping to see or feel when you first looked at yourself wearing it?

That is actually the part I still don't understand. What did "right" mean? I don't know.

I was curious. I wanted to see what I would look like and know how I would feel. And if I'm completely honest, I didn't know whether I would like it or whether some part of me would be repelled by it. That sounds strange now, but it's true. I think I was testing something. Would I look in the mirror and think, oh God, no? Would I find the whole thing ridiculous or somehow repulsive? Or would I like what I saw? I didn't know.

What I did know was that I wanted to see myself looking feminine. I liked the idea of that. Somewhere in there was probably the thought that perhaps eventually I could even look hot. That appealed to me. But I can't give you some profound explanation for why it appealed to me. I just wanted it. I wanted to see what happened when I looked in the mirror and saw something feminine looking back.

When you did look in the mirror, what happened?

I was disappointed.

There was something terribly sad about it because I recognised the person looking back at me. I knew her. Except it was almost as though I had put her into a time machine and she had come out the other end a quarter of a century older.

There were inevitably some what-ifs. What if I had done this then? What if all those years hadn't passed? But strangely, even those thoughts were quite fleeting. I still hadn't really bought into the idea that I was going to do anything about this. I wasn't standing there thinking, right, I'm going to transition. I think I was simply responding to an urge. I wanted to see her again. And when I did, I recognised her.

But time had happened to both of us.

Did you feel ashamed of the person you saw? Or merely disappointed by what time had done?

No. I don't think I felt shame. I felt disappointment, certainly. But more than anything else, I felt sorry for her.

That sounds strange even saying it now, but it's true. I looked in the mirror and thought:

Oh dear God. You've been in here all along, you poor thing.

And I'm not imposing some neat narrative on it afterwards. I genuinely think that was the feeling.

Fuck. Jesus. You never went away, did you? You're still here.

And then another thought followed almost immediately. How did I not see you for all those years? How had I managed to go for so long believing this part of me had disappeared when apparently she had simply been there all along?

This is going to sound horribly poetic, but I think I felt protective of her. I looked at that person in the mirror and felt sorrow for her, not disgust. Maybe that mattered. Instead of looking at this part of myself and thinking, you need to be hidden again, something in me was saying:

This person needs looking after.

When you felt protective of her, who were you protecting her from? Other people? Society? Or were you protecting her from Steve, from the part of you that had shut her away before?

Oh my God. Before I even got to the end of that question, my head was shouting:

Steve.

Steve.

Steve.

That was who I wanted to protect her from. Not the world, not other people. Steve. I didn't want Steve to fucking destroy this person again.

And that feels enormously important now that I say it out loud. For most of my life, whenever Stevie appeared, I had effectively stood on the other side of the room from her. I was the one judging her, frightened of her, trying to control her, contain her, drug her away, sober her away, marry her away, work her away, cure her and eventually convince myself that she had disappeared altogether.

Then I looked in the mirror all those years later and somehow I wasn't standing over there anymore. I was standing beside her. I felt sorry for her. I wanted to protect her.

Maybe for the first time the person I regarded as the threat wasn't Stevie. It was the part of me that might shut her away again.

If Steve was the danger, what did you think he had actually taken from Stevie? What were you mourning for her?

I think there was a dual feeling.

It was time. God, so much time had gone. There was inevitably grief in that. And there was guilt too, because by then I had raised a family. I loved them. I really did love them. Nothing about discovering this other part of myself suddenly made that life false. Those two things can be true at the same time.

But there was something else. I felt sorry for Steve too. I almost wanted to say to him:

Fucking hell, Steve. What did you carry?

Because he carried an enormous amount and never let the world know. He got on with things, built a life, raised a family. And all the while he was carrying something that nobody looking at him could possibly have understood. It wasn't easy for him.

So I don't think I looked backwards and saw a villain who had imprisoned Stevie for twenty years. I saw two people who were actually the same person. I felt sorrow for Stevie because of all the time she had lost, and sorrow for Steve because of what he had needed to do to survive those years.

Bit of everything, really.

You'd spent twenty years being normal, and it had worked. What happened to that?

Not at the exact moment I ordered the first dress. I don't think I had some grand philosophical revelation while clicking "buy". But it didn't take long.

I remember lying in bed and thinking about all the people this could hurt. And then I had this very stark thought.

You are going to be dead for a million years. Nobody is going to care who Stephen David Bennett was. Then you'll be dead for another million years. And another million after that. For the rest of eternity you will simply be gone. With a good wind, maybe you've got thirty years left. Forty if you do spectacularly well.

You have to stop running. You just have to stop running.

That became enormously important to me. And alongside it, another realisation started forming. I had spent years making deals with myself. If I just do this, I'll be happy. If I try this version of life, perhaps I'll finally be happy. And none of the deals ever quite worked.

I had done normal. I had done it extremely convincingly. People thought I was being myself. I absolutely was not. And by this point I had begun to feel like the person in the background of my own life.

So I think releasing Stevie became entangled with something larger. It wasn't simply, I want to wear a dress. It became, I have had enough of disappearing inside my own life. I wanted to cut loose. I wanted to know what being myself actually felt like. And once that feeling started, it became overwhelming.

Did Stevie become possible because you stopped being ashamed of being trans, or because you had finally become more frightened of wasting your life than of being abnormal?

That's difficult to separate because I think the two things blossomed at exactly the same time. I don't think one clearly caused the other. The feeling that I had to stop running, stop living in the background of my own life, that was growing. And at the same time, Stevie was coming back. They seem almost fused in my memory. The more strongly I felt that I couldn't keep living as I had been, the more impossible it became to keep her buried. And the more she came back, the more obvious it became that I had been living a version of my life that was no longer enough.

But none of that meant I instantly accepted what it meant. It took an enormous amount for me simply to say the words to myself: I am transgender. That was a massive threshold.

And bizarrely, there was another one which may have been even harder.

Holy fuck. I'm LGBT.

I really struggled with that. In some ways, I still do. I had spent my whole life regarding that as a world somewhere over there. Then suddenly I had to confront the fact that, whether or not I identified with every part of its culture, I belonged somewhere underneath that enormous umbrella. I'm not sure I have ever completely reconciled myself to that.

So this wasn't a simple story in which I suddenly became liberated and thought, wonderful, I'm trans, everything makes sense. Some parts of accepting myself came remarkably easily. Other words remained incredibly difficult to say. And somehow both things were happening at once.

Why was saying "I am transgender" so difficult?

I knew that once I said it, I would probably act on it. That is my nature. I don't tend to say something important, acknowledge it, and then sit passively beside it for five years. So saying "I am transgender" wasn't simply attaching a label to myself. It meant something was going to happen. Once the words were out, I knew I would probably start moving.

But the extraordinary thing is that once I finally said them, I felt an enormous sense of relief.

Holy fuck. I've given myself permission.

That was what it felt like. Permission. And it felt good.

In fact, once I had said it once, I couldn't seem to stop saying it. There were plenty of days when everyone was out of the house and I would spend the day in my office as Stevie. And I remember going back to the mirror constantly, genuinely perhaps once an hour, looking at myself in whatever I happened to be wearing and saying it again.

I'm transgender. Holy fuck. I'm transgender.

Over and over. It was as though I was testing the words to see whether they still worked. And every time, they did.

Once I crossed that line, it wasn't shameful. It was fucking liberating.

What exactly had you given yourself permission to do?

I think it was permission to embrace it. And perhaps that is much closer to the shame question than I realised.

Because once I said the words "I am transgender", I wasn't merely describing myself. I was giving myself permission to stop fighting it, to stop treating it as something that had to be contained, explained away, postponed or cured. Maybe simply saying it was part of what got rid of the shame.

It felt like a weight lifting. A really big one. Even thinking about that moment now makes me slightly tearful.

Because perhaps I had spent so many years refusing to say the thing plainly that the shame survived inside the refusal. Then I finally said it. I am transgender. And nothing terrible happened inside me. Quite the opposite.

When you remember saying "I am transgender" now, who are the tears for? Stevie? Steve? The years that had gone? Or are they tears of relief?

Relief.

That was the word that came into my head before I even got to the end of the question. Not grief, not pity. Just enormous relief. And with it, calmness. Happiness. It felt as though something inside me had finally stopped fighting.

That is what I remember most clearly now.

Was the shame tied to the constant effort of containing Stevie? Did saying the words finally mean, "I am done containing this. I am going to let it exist"?

I think when you deny something, you deny facing it. You never quite confess it, even to yourself. As long as you don't say it out loud, you can keep circling around it. You can treat it as an urge, a phase, something you once had and might somehow get rid of again.

But once you actually say "I am transgender", there is something almost like lancing a boil. The pressure goes. It deflates.

Because at that point, you would have to be some kind of bloody fool to stand in front of a mirror, say "I am transgender", accept that this is true, and then immediately say, and I fucking loathe transgender people. Or, and I feel deep shame because I am one. Those two positions suddenly became much harder to hold at the same time.

I think that may genuinely be what happened. The shame had survived partly because I had never fully admitted the truth to myself. Once I did, there was nowhere for quite so much of it to hide.

Imagine you could sit beside the Stevie who had just put that first dress on. She is disappointed by the mirror. She is older than she remembers. She has no idea what happens next. What does she need to hear?

You're still a good person.

This is going to be tough, but you're a good person.

Don't forget that.

That's it. I don't think she needed to be told that she was definitely going to transition, or that everything would work out. She needed to know that whatever this was, it didn't make her a bad person. That she hadn't suddenly become something lesser. That she was still good.

And perhaps more than anything else, that was the thing I had finally begun to believe myself.

So, what did we find?

At that point I asked the model to stop interviewing me and tell me what it thought had actually happened. This was its conclusion.

The deepest thing came almost accidentally. When asked what the woman in the first dress needed to hear, you didn't say "you're beautiful" or "it'll all work out". You said: you're still a good person.

That may be the heart of the whole thing. Shame had spent years telling you that Stevie's existence said something about your character. And somewhere along the way, perhaps before you even understood that it had happened, you stopped believing it. You didn't yet know what you were going to do. You didn't know whether you would transition. You weren't even sure you liked what you saw in the mirror. But you had stopped believing that wanting to see her made you bad.

That may be what "no shame" actually meant.

Well.

Fuck.

I genuinely did not think this was going to work. I really didn't. When I started the interview, I thought we would probably uncover a few interesting things. We would wander around some old memories, find a couple of connections I hadn't spotted before, and there would probably be enough mileage in it to justify putting the experiment into the article. I did not think I was actually going to get an answer.

But I think I did.

And irritatingly, having spent all this time trying to find some complicated psychological explanation, the answer sounds almost embarrassingly simple.

I accepted what I was.

That's it. I accepted what I was. I know how bloody obvious that sounds when you read it written down. Of course shame disappears when you accept yourself.

Thank you, Stevie. Groundbreaking work.

But it didn't feel obvious to me. Not at all. I had spent years assuming that something must have happened to the shame. Maybe society had changed enough, or I had seen enough trans women online getting on with their lives. Maybe I had simply got older and stopped caring what other people thought. And I am sure all of those things helped.

But I think the important thing happened inside. I stopped arguing with the fact.

So I said the words again. I'm transgender. Holy fuck. I'm transgender. And it felt good.

Because once I accepted that this was simply true about me, there was another thing I apparently accepted at the same time without ever putting it into words.

It didn't make me a bad person.

That was the bit I couldn't see when I started writing this. And strangely, that is the bit that has made me emotional while writing it now. Because when I was asked what I would say to that frightened, disappointed woman looking at herself in the mirror in her first dress, the answer came instantly.

You're still a good person.

Maybe that is all shame ever really needed from me. Not a political argument or a theory of gender, and not somebody telling me I was stunning and brave. Just permission to stop treating myself as if I had committed some terrible offence by existing.

And I genuinely feel relieved to understand that.

I started writing this essay because there was something about myself that I could not explain. I think I can explain it now.

And if you are reading this with some version of the same thing sitting inside you, something you have spent years hiding, negotiating with, suppressing or feeling ashamed of, I'm not going to pretend that my answer automatically becomes yours. It might not.

But perhaps there is one question worth asking yourself. Not whether everyone else will accept you. Not even, yet, what you are going to do about it.

Just this.

If this thing about me is true, does it actually make me a bad person?

Because perhaps shame starts to lose its grip when the answer is finally:

No.

I was lying in bed at about three o’clock in the morning last night, dictating notes into my agentic PA to dump onto tomorrow’s Kanban board.

One of them was about a department I’ve been designing inside Relay, the little agentic company I’m building around myself.

It sits between Discovery, whose job is essentially to find economically interesting things, and Engineering, whose job is increasingly to throw armies of AI agents at building them.

I’ve been calling this middle bit Shaping.

The idea seemed perfectly sensible. Discovery finds an opportunity. Shaping works out what the product should be. Engineering builds it.

And then, at three in the morning, I suddenly thought:

Jesus Christ, Stevie. That is not how you develop anything whatsoever.

Worse, I have spent years arguing against precisely that pattern.

The fact that software engineering is becoming cheap as chips does not suddenly make bad product development good product development.

If anything, it makes the mistake easier.

Because when building things becomes ridiculously cheap, you can build a phenomenal amount of stuff that nobody wants.

MVP does not mean “version one”

Before I explain where I think I went wrong, I need to talk about a book.

The Lean Startup, by Eric Ries.

I actually read the bloody book. Twice.

This distinguishes me from an alarming percentage of the people I have heard quoting its most famous acronym ever since.

MVP. Minimum Viable Product.

Oh, my dear God, MVP.

I have sat through more meetings than I care to remember in which somebody has announced, with great authority:

“This will be the MVP version.”

And I have felt my eyeballs quietly rolling into the back of my skull.

Because somewhere along the way, MVP came to mean:

Version one, but a bit shit.

Take the product you have already decided to build, remove a few features, launch it earlier and call it an MVP.

That is not the interesting idea at all.

The interesting idea is:

What is the minimum thing we need to create in order to test the important hypothesis?

Sometimes that is software.

Sometimes it is a landing page.

Sometimes it is a manually delivered service.

Sometimes it is a spreadsheet.

Sometimes it is an advert.

Sometimes there is a human sitting behind a curtain pretending to be the automation you haven’t built yet.

And sometimes it is a video.

Which brings me to Dropbox.

Dropbox didn’t build Dropbox to prove Dropbox

Dropbox had an awkward problem in its early days.

“File synchronisation” did not sound terribly revolutionary.

Files already existed. Online storage existed. File-sync products existed. You could quite reasonably hear the pitch and say:

“So what?”

The magic was in the experience.

Put a file in a folder on one machine and it silently appears on another. Change it somewhere else and everything stays in sync. Conflicts get handled. The whole thing mostly disappears into the background.

But building that properly is difficult.

So rather than build the entire thing before establishing whether anyone cared, Dropbox demonstrated the proposed experience with a video.

People cared.

A lot.

And that is the important distinction.

The video was not Dropbox version one.

It was the minimum product required to test whether people wanted the thing Dropbox was proposing.

A completely different idea.

Meanwhile, in Docklands

A few years later, I was commuting into London every day and reading The Lean Startup on the train.

I got to the Dropbox story.

I remember thinking:

That is brilliant.

I was building Dropbox.

Well, a Dropbox clone.

It was called Zettabox, and I was one of two developers working on it.

The central commercial thesis was essentially this:

European customers will not want their files stored in America. They will prefer a cloud-storage service that keeps their data in Europe.

And the chosen method for testing this hypothesis was apparently to spend millions building Dropbox again.

You have to admire the commitment.

We built the thing, and I worked like a dog on it.

File synchronisation is an unpleasantly serious piece of software.

Get the colour of a button wrong and somebody gets irritated.

Get synchronisation wrong and you have just deleted Granny’s only photographs of Grandad.

There are conflicts, partial uploads, offline machines, files renamed in two places at once, networks disappearing halfway through things and an endless collection of edge cases waiting to eat somebody’s data.

And underneath all this engineering was one rather important question:

Did enough people actually care where their files were geographically stored to switch provider and pay us?

You could test that question without building Dropbox.

Put up a page.

Run some ads.

Offer:

European-only cloud storage. Your files stay in Europe.

Ask for money.

See what happens.

The product disappeared a couple of years later. My recollection is that roughly £10 million had gone into the whole adventure by then.

They could have given me £1 million and saved the other nine.

I’d have rung my mother.

“Mum, do you care whether your files are stored in Virginia or Frankfurt?”

“No.”

There we are.

Invoice attached.

Cheap software doesn’t make bad ideas good

This is what hit me at three o’clock in the morning.

Software production inside Relay is becoming extraordinarily cheap.

Increasing amounts of the engineering are performed by autonomous agents. They can investigate problems, write code, run tests, review each other’s changes and increasingly keep going without me sitting there supervising them.

That is wonderful.

But it does not repeal reality.

Making the wrong product ten times cheaper does not make it the right product.

And I realised that my original definition of Shaping was backwards.

Its first question should not be:

“What should Engineering build?”

It should be:

“What has to be true for this idea to work, and what is the cheapest possible thing we can do to force reality to tell us whether we are right?”

That is what I actually mean by an MVP.

Sometimes, for an idea to die, it has to live

Here is a deliberately silly example from something we have been throwing around recently.

Suppose one of my Discovery agents comes back with this:

Find Airbnb properties with ordinary listing photographs and use AI to generate convincing moving, three-dimensional-style walkthrough footage without anybody physically visiting the property. Sell that new marketing asset to the owner.

Fine.

But that isn’t a product yet. It is a collection of hypotheses.

Can current AI actually produce something convincing enough?

Can it do it cheaply?

Can we mechanically identify suitable properties?

Does the asset genuinely look more valuable than the source photographs?

Do owners care?

Will they pay?

Can agents operate almost the entire thing without accidentally turning me into Chief Executive of Making Airbnb Videos?

Those are the questions.

And this is the awkward bit: research can only take you so far.

Sometimes, for an idea to die, it has to live for five minutes in the real world.

So perhaps we make three examples.

Perhaps we create one simple page.

Perhaps we show them to ten property owners.

Perhaps we ask for £100.

Nobody buys?

Excellent.

We have learned something before building the Airbnb Three-Dimensional Artificial Intelligence Property Marketing Platform™, hiring a sales team and producing a seventeen-slide roadmap.

Maybe people love the output but won’t pay £100.

Change the price hypothesis.

Maybe Airbnb hosts don’t care but wedding venues do.

Change the buyer.

Maybe nobody wants the 3D walkthrough but estate agents pay for thirty-second social-media reels.

Change the mechanism.

The MVP can be thrown in the bin afterwards.

That is fine.

Its job was to produce evidence.

Concierge before automation

I already work this way constantly inside Relay, the agentic operating system I’ve built. I just hadn’t properly connected it back to MVP thinking.

I use the phrase:

“We’re going to concierge this.”

By that I mean: do the process in the crudest way necessary to find out whether it is useful before automating the hell out of it.

I have small recurring research agents I call Sentinels.

One might have a job like:

Once a week, look at what is changing in agentic software development, compare it with what Relay currently does and tell the Relay Foreman if we appear to be missing anything important.

Eventually, that could be beautifully automated.

It could schedule itself, gather evidence, cross-reference company knowledge, create work and monitor what happened afterwards.

Wonderful.

But I do not begin by engineering all of that.

Initially I might have an agent with a rough prompt and manually trigger it.

Run it.

Was the report useful?

Did anybody act on it?

Did it discover anything important?

Run it again next week.

Still useful?

Good.

Now earn the automation.

That is a minimum viable product.

The MVP should try to murder the idea

This, I think, is the bit that has been most thoroughly lost in the modern interpretation of MVP.

The MVP is not there to justify the thing you already want to build.

It should be trying to kill it.

Ask:

Which assumption, if false, destroys this idea fastest?

Then test that one.

If your entire business depends on customers paying £500, there is little value spending three months proving that you can technically produce the thing for £7 if nobody will pay £500 for it.

Likewise, if technical feasibility genuinely is doubtful, prove that before spending weeks designing the sales process.

The order should follow uncertainty, not the org chart.

This also makes early roadmaps rather suspect.

I have seen versions of this countless times:

Q1: build features.
Q2: build more features.
Q3: discover nobody wants it.

I would prefer to bring Q3 forward.

Once the dangerous assumptions survive contact with reality, then by all means make the roadmap.

Until then, a beautifully planned roadmap is often just beautifully formatted fiction.

I may have to rename the Shaping Department

I’m not sure yet whether Shaping survives as the name.

But its job has changed completely in my head.

Discovery should hand it an economic hypothesis.

Something like:

We believe buyer X experiences problem Y and may pay for outcome Z.

Shaping should then identify the assumptions inside that sentence and work out the cheapest sequence of experiments capable of proving or killing them.

Only after enough of those assumptions survive should Engineering receive anything resembling a durable product mandate.

That seems particularly important now because of the strange irony of agentic software development.

We are rapidly approaching a world where building is no longer the expensive part.

Knowing what deserves to be built is.

If ten autonomous software engineers can build your terrible idea over the weekend, somebody still needs to make sure it is not a terrible idea.

Otherwise all we have invented is a much faster way to build Zettabox.

And I’ve already done that once.

I’m not doing it again.

It’s Saturday afternoon and I’m sitting in my office doing what I apparently now regard as relaxing.

Working on Relay.

It’s going really well. I’ve made a fairly major change to the way my Eisenhands system works, given myself a Commercial Foreman to kick arse in much the same way as my software Foreman does, and learned yet another lesson that I seem to have to learn repeatedly:

Stop sticking deterministic code everywhere and get out of the bloody way.

The agents know what they’re doing.

Chesterton, meanwhile, is clawing desperately at my chair because he has decided the only acceptable place for a six-pound chihuahua is directly on top of me.

And somewhere in the living room, YouTube is still running.

I’d been watching a bit of telly this morning because it’s Saturday and I occasionally pretend to be a normal person. YouTube then wandered off by itself into a succession of videos about converting trucks into camper vans.

I am so tempted.

Honestly.

I could absolutely do it.

Someone stop me.

But eventually YouTube exhausted camper vans and decided that what my Saturday afternoon really needed was Triggernometry.

Oh dear.

If you’ve never seen it, Triggernometry is basically Konstantin Kisin and Francis Foster sitting in a studio discussing whatever enormous question humanity has failed to solve that week.

I always feel slightly sorry for Francis Foster.

Konstantin is clearly the interviewer. Francis increasingly seems to have been assigned the role of the bloke who occasionally says something funny, mentions having been a teacher and asks a slightly dopey question while Konstantin waits patiently to resume the interview.

I imagine Francis is perfectly aware of this.

(watch one minute of this, its quite funny)

Anyway.

That isn’t actually the point.

I’m sitting here half working, half listening, and every so often something floats through from the living room.

The trans debate.

Oh, here we bloody go.

What does it mean to be English?

Is Rishi Sunak English?

Something about the Middle East.

Something about immigration.

Something about economics.

Another enormous subject.

Another enormous subject.

Another enormous subject.

And suddenly I thought:

God. I used to do this.

Not podcasting.

The other bit.

Trying to solve the outside world as a substitute for solving the inside one.

I used to have opinions about absolutely everything.

Bond markets.

Politics.

Geopolitics.

Immigration.

The Middle East.

Monetary policy.

The European Union.

Whatever enormous complicated subject happened to appear in front of me, I would construct a thesis about it.

Usually just enough of a thesis to sound clever in a pub.

The Pub Man Expert.

I once went on a family holiday to Italy and took with me a book about the history of the Federal Reserve.

Not a little airport book about money.

The history of the Federal Reserve.

In immense detail.

There I was, surrounded by Italy, my family presumably doing normal holiday things, while I sat there diligently studying the institutional history of American monetary policy like Jerome Powell might ring me on Tuesday morning and say:

“Steve, mate, I’m really stuck on this one. What do you reckon?”

Honestly.

I actually did this.

And I thought this was a perfectly reasonable way to spend a holiday.

The strange thing is that almost none of it had any practical relationship with my life whatsoever.

Suppose I became the world’s leading amateur expert on Israel and Palestine.

Then what?

I’m not negotiating a peace agreement.

Suppose I developed the definitive theory of British immigration policy.

Then what?

Nobody is ringing me from Downing Street.

Suppose I correctly diagnose what central banks should do with interest rates next year.

Lovely.

They still aren’t asking me.

There is obviously nothing wrong with being interested in the world. Curiosity is good. Understanding things is good.

But there is a point where curiosity turns into something else.

Information porn.

And I think there is a particular type of man who is incredibly susceptible to it.

I know because I was one.

Endlessly consuming opinions.

Endlessly constructing arguments.

Endlessly finding another gigantic external problem to think about.

Because there is something wonderfully comforting about problems you cannot actually solve.

They require nothing from you.

You can spend six hours analysing the collapse of Western civilisation and still avoid making the phone call you’ve been putting off for three weeks.

You can develop a sophisticated theory about masculinity while having absolutely no idea who you are.

You can diagnose everything wrong with society without ever asking what might be wrong with your own life.

And because the subjects are enormous and serious, it feels productive.

It feels intellectual.

It feels important.

It isn’t avoidance.

You’re engaged with the issues.

I look at some men now and I recognise it instantly.

Ukraine.

Gaza.

Trans people.

Immigration.

Trump.

Woke.

Anti-woke.

Masculinity.

Civilisation.

Birth rates.

The end of Europe.

One enormous external abstraction after another.

And underneath it all, sometimes, I wonder if there’s just a bloke who really doesn’t want to sit quietly in a room and ask himself one considerably smaller question:

Am I actually happy?

I certainly didn’t.

And so, instead of going back to Relay, I stopped what I was doing and started writing this article.

I’ve just reached the end of draft one.

And dear God.

From the living room, Triggernometry has moved on again.

They’re now talking about the bloody Vikings.

I kid you not.

The Vikings.

We have apparently finished with trans people, immigration, national identity, the Middle East and the future of Western civilisation, and have now moved on to solving Nordic historical problems.

It’s almost too perfect.

Chesterton has finally got onto my knee.

I’m going back to my software.

The lads can sort out the Vikings.

It’s a Friday afternoon in Cork and my Relay system seems to be ticking over nicely. Code is coming out, workers are working, everyone seems happy, so I thought I’d turn my attention to this.

This is a subject I’ve been asked about quite a lot. I’ve described, in frankly immense amounts of detail, exactly how I transitioned, what surgery I had done, what worked, what didn’t and all the rest of it. But I haven’t really talked very much about what I’ve done to my face apart from the surgery.

And there has been quite a lot.

This isn’t going to be War and Peace. I’m not attempting to write the definitive guide to aesthetic medicine. I’m simply going to tell you what I did, why I did it and roughly what order I did it in.

Because if you walk into almost any skin clinic, for want of a better term, you will be confronted by a gazillion different treatments: microneedling, RF microneedling, fractional lasers, CO2 lasers, Erbium lasers, IPL, BBL, chemical peels, radiofrequency tightening, ultrasound tightening, PRP, skin boosters, fillers, Sculptra, Radiesse, and an endless parade of machines with names like Morpheus8, Potenza, Ultherapy, Thermage and God knows what else.

Half of them sound as though they should either be attacking a small country or appearing in a Marvel film.

Some of these things are genuinely very good. Some might be very good for you, but completely pointless for me.

That is the important bit.

Before spending any money, I think you need to work out what problem you are actually trying to solve.

Three different problems

This is how I eventually came to think about my own face:

Laxity. Volume. Skin quality.

They overlap, obviously, but they are not the same problem.

Laxity is basically how firm everything is. If you’re pushing 40 or 45, there’s a reasonable chance things aren’t quite sitting where they did when you were 25.

Although not always.

I know one trans woman who is 51. I was sitting next to her in a car the other week looking at her face and she has virtually no skin laxity whatsoever.

You bloody cow.

I did.

The mistake I think people make is trying to solve substantial laxity by throwing hundreds and hundreds of pounds or euros at comparatively small treatments.

€500 here.

€600 there.

Another €700 six months later.

None of these things are cheap. They’re just cheap relative to surgery.

There are non-surgical treatments that can tighten skin to a degree, particularly if the problem is fairly mild. But if you have significant facial and neck laxity and want a significant result, you are eventually getting into facelift and neck-lift territory.

Sorry.

I was.

Volume is a completely different problem. I had lost an enormous amount of it. My mid-face was virtually concave when I started.

I’d lost significant amounts of weight twice in my life and done years of endurance cycling, and I had very hollow cheeks. At the time I thought it made me look lean and masculine.

Which, unfortunately, it did.

It just wasn’t remotely what I wanted when I started trying to make my face look female.

Then there is skin quality itself: thickness, texture, pores, pigmentation, fine lines, smoothness, sun damage and that slightly crepey quality skin can acquire as it ages.

So those were my three problems.

And I started attacking them.

The nuclear option

When I first transitioned, before the FFS, before the facelift, before everything else, I sat down and looked at the enormous list of things I could supposedly do to improve the actual quality of my skin.

Then I ranked them.

Sitting at the top was CO2 fractional ablative laser.

This was the hard hitter. Not the pleasant option. Not the lunchtime option. Not the pop in on Thursday and nobody at work will notice option.

This was the one where I effectively had to disappear for the best part of eight or nine days because I came out looking like a burns victim.

It is brutal.

My God, though, it works.

I’ve had it done twice. More on round two later.

The first time I had my whole face done, my neck and even my eyelids, and I had absolutely no idea what I was letting myself in for.

They put me on a bed in the clinic, anaesthetised the area around my eyes, and then inserted these little metal shields underneath my eyelids. Essentially enormous metal contact lenses with tiny handles on them.

Why?

So they could laser my bloody eyelids.

The things I will do for beauty.

The recovery was horrific. For the best part of a week I looked like some sort of monster.

Then it healed.

And the results started appearing.

If somebody said to me, “You get one serious skin-resurfacing treatment. Pick one,” I’d pick this.

It made a massive difference to me.

Where I initially got fillers completely wrong

My first experience with filler and Botox was before transition. I went into a clinic presenting completely as a man.

And almost immediately, something ridiculous happened.

The doctor spotted my Rolex.

Then we somehow got into that peculiar thing men occasionally do where each one starts subtly trying to out-impress the other.

You know the sort of thing.

A little man-off.

And I participated enthusiastically because, apparently, I was an idiot.

I walked out afterwards and thought:

You fucking idiot, Stevie. What are you doing?

Because not only had I walked into an aesthetics clinic presenting as a man, I had then spent part of the consultation performing masculinity with the bloke who was about to inject my face.

Unsurprisingly, he gave me the most masculine filler imaginable. Definition, angles, chiselling. He had looked at the man sitting in front of him and tried to make him into a better-looking man.

Entirely reasonable.

Also precisely the opposite of what I actually wanted.

A few months later, I tried again.

I was still at the stage where I thought filler might be capable of doing quite a lot of the heavy lifting. I already knew I probably needed a facelift eventually, but my mid-face was badly depleted and everything was rather, shall we say, soggy.

I thought perhaps filler could fill it out temporarily while I worked out what I was going to do properly.

This time I went somewhere completely different.

And this time I told her everything.

I was still presenting male when I walked through the door, but I showed her a photograph of Stevie.

She looked at the photograph.

Then she looked at me.

Then back at the photograph.

Her expression basically said:

Who the hell is that?

“That’s me,” I said.

“That’s the other me.”

So I explained.

From that point onwards, everything was aimed at the female face I was trying to create.

We added volume to the cheeks and it helped to a degree, but I was still asking filler to do far too much.

Eventually I realised that.

So I stopped.

Completely.

I decided I would deal with the actual structure first and come back to filler later, if I still needed it.

That turned out to be one of the better decisions I made.

Botox

That second clinic was also where I started doing Botox properly.

In my head, I divide Botox into two types.

The first is ordinary anti-wrinkle Botox: forehead, frown lines, crow’s feet, the usual areas.

Something I didn’t appreciate initially was how cumulative the cosmetic result could be. Obviously the Botox itself starts working quite quickly, but if you already have established expression lines, one round isn’t necessarily going to erase years of creasing.

What happened to me was that repeated treatment stopped me continually folding the same bits of skin in the same places, and over time everything became much smoother.

I have a before-and-after photograph I’ll include here. Both pictures are pre-FFS. No facial surgery whatsoever.

The difference is significant.

Incidentally, the second photograph is also rather poignant for me. It is the very last photograph of me as a man.

I think about a week later, he was gone.

The second type is what I rather unscientifically think of as atrophy Botox.

The obvious example is masseter Botox, where much larger quantities are injected into the muscles at the side of the jaw with the intention of weakening them and, over time, reducing some of their bulk.

If you are trying to feminise a square lower face, you can probably see the attraction.

I did this twice.

The first time was quite funny. I was still living with my family and I think we had steak for dinner that evening.

Oh my God.

My jaw was knackered.

I sat there chewing and chewing and thinking:

For Christ’s sake, why is eating this steak suddenly an endurance sport?

Whether it made a gigantic visual difference to me, I’m not entirely sure.

But I did it.

Twice.

I’ve also done the smaller tricks, like lip-flip Botox.

Chasing collagen

Around all of this I became increasingly interested in collagen.

I started taking hydrolysed collagen every morning, which I’ve now done for years. Am I absolutely convinced it makes a dramatic difference? No. I do it anyway.

More interesting to me was Sculptra.

Sculptra is made from poly-L-lactic acid, or PLLA. Rather than simply behaving like a conventional filler and creating immediate volume, the idea is to stimulate a gradual tissue response and collagen production.

One of its early medical uses was treating facial lipoatrophy in people living with HIV, which immediately caught my attention because, structurally at least, a depleted face was exactly one of the problems I was trying to solve.

So I had Sculptra.

I liked the philosophy of it: rather than endlessly adding more filler, encourage the face to rebuild some structure of its own.

And, by the way, I also microneedle my face every so often.

The structural work

Eventually I had the FFS and facelift.

Initially, everything looked extraordinary.

Partly because the work was extraordinary.

Partly because my face was swollen to approximately the size of Belgium.

As the swelling disappeared, though, it became obvious that I still had a lot of volume depletion through the mid-face.

So I moved on to fat grafting.

I was warned from the outset that I might need several rounds because not everything survives.

I was deeply unimpressed by this information.

I had rather hoped they could put it in once and we could all go home.

But no.

The first round helped a lot, but I still didn’t have the underlying projection and structure I wanted.

So my next trick was...

Cheek implants.

I know.

I am slightly extreme.

Little incisions inside the mouth, solid implants positioned over the cheekbones, and suddenly the soft tissue had something underneath it that had been missing before.

Scaffolding.

That made a substantial difference.

There was still some hollowing lower down, so I had another round of fat grafting.

Again, better.

Much better.

Still not quite there.

And this is where filler finally became brilliant.

Architecture versus finishing work

By this point, the lifting had been done. The implants were in. The fat grafting had restored a lot of the missing volume.

I wasn’t asking filler to rebuild my face anymore.

I was asking it to finish it.

I had filler placed into the medial cheeks and suddenly it worked spectacularly well. That relatively small amount of additional volume filled the remaining hollow and tied everything together.

That was when filler finally made sense to me.

Early on, I had been trying to use filler as architecture.

Later, I used it as finishing work.

And it was vastly better at the second job.

Lips

I’ve also had several rounds of lip filler over the years because I started with virtually no lips whatsoever.

Honestly.

Two little elastic bands attached to the front of my face.

I haven’t gone for gigantic lips. I just wanted enough to give my mouth some actual shape and definition, and it has helped enormously.

These days all of this is much less intensive. I might have a little medial-cheek filler when it needs it, some lip filler perhaps once a year, and Botox roughly every four months in the normal girly bits.

That’s about it.

At this point you’re probably thinking:

Jesus Christ, Stevie. Is there anything you haven’t done?

We haven’t even got to the bathroom cabinet yet.

The bathroom cabinet

At some stage I researched the living hell out of skincare.

My morning routine is actually fairly simple.

I cleanse in the shower. I buy decent cleanser, although I’m not entirely convinced this is an area where anyone needs to spend a fortune. We still have a few irritating little hairs to shave off as well, which is depressing, but we’re getting there.

Every other day or so I use an AHA/BHA exfoliant. At the moment it’s just The Ordinary.

Then hyaluronic acid for hydration and a bit of plumping. I’m currently using Vichy, although again, I doubt you need to spend much money here.

The first thing I really care about is vitamin C. At the moment I’m using La Roche-Posay C12.

Then comes the least glamorous but probably most important part of the whole routine: SPF 50.

Every day, whatever the weather. Even when Ireland is doing that weird thing where it looks as though somebody has placed a grey Tupperware lid over the entire country.

SPF 50.

Then moisturiser.

Done.

Night-time Stevie

In the evening I use a serum. At the moment it’s some Clarins one I got relatively cheaply and, if I’m being completely honest, didn’t research to within an inch of its life.

It feels nice.

That’s about the strength of my scientific conclusion.

Then comes tretinoin.

For me, this is one of the serious parts of the routine.

I now use it almost every night, but I absolutely could not do that when I started.

Oh God, no.

Before I’d even had my facelift, I went through a phase of pushing my luck with it. If I used it too many nights in a row, particularly around the eyes, there would eventually be consequences.

I remember waking up one morning and my skin was flaking, the area beneath one eye had dried up and crinkled, and I looked like Emperor Palpatine from Star Wars.

I stared at myself in the mirror and thought I had finally overcooked it.

So I backed off, started again, backed off, started again, and gradually my skin became much more tolerant of it.

Mine is prescription strength, although I acquired my current mountain of tubes over the counter in Bangkok.

I bought enough to survive a small apocalypse.

At the current rate I should probably make it into 2027.

Then moisturiser.

Bedtime extras

I also have two LED masks, one for my face and one for my neck and upper chest.

Both run for about ten minutes, so I generally use them when I get into bed.

You are imagining me lying there looking like Darth Vader’s high-maintenance sister.

But it’s ten minutes while I’m already doing absolutely nothing, so it doesn’t particularly inconvenience me.

I’ve also just started another experiment: prescription estriol cream on my face twice a week, replacing tretinoin on those nights.

There is some interesting research around topical oestrogens and ageing skin, particularly collagen, thickness and hydration. But there is a fairly enormous difference between interesting research and everyone should smear hormones on their face.

I’m trying it.

That’s all.

Whether it does anything spectacular for my skin remains to be seen.

Ask me in six months.

And finally, the controversial one

Right.

Here we go.

The blue liquid.

GHK-Cu.

Copper peptide.

GHK-Cu is a naturally occurring copper-binding peptide in the body which has attracted quite a lot of interest around tissue repair and skin biology.

You’ll find copper peptides in perfectly ordinary topical skincare products.

That isn’t the controversial bit.

I inject mine.

Daily.

And before anybody starts ordering syringes because Stevie Bennett said so on the internet:

don’t.

Injectable GHK-Cu for cosmetic skin improvement is nowhere near as established as sunscreen, tretinoin or Botox. The evidence base is much thinner and this particular corner of the market can be something of a regulatory Wild West.

I’ve read about it and made my own decision.

That does not make it a recommendation.

The boring things

Beyond all of that, I do the boring things.

I drink a lot of water and have done for twenty-odd years. I don’t sunbathe. I stay out of strong sun where I can. I wear SPF. I generally eat pretty well.

Not perfectly.

I am a human being.

But pretty well.

Day to day, none of this actually feels particularly onerous. Morning skincare takes a few minutes, evening skincare takes a few minutes, and the LED happens while I’m lying in bed. Botox is every few months. Fillers are occasional.

The giant interventions happened over years.

Am I finished?

Not quite.

I still have some electrolysis to finish around my chin and mouth. Once that is finally done, I’m going to reassess the skin in that particular area.

And this is where that second CO2 treatment comes in.

I had another round focused there and, disappointingly, it didn’t make as much difference as I’d hoped.

So there is still some work to do.

The cheeks are a completely different story. Between the resurfacing, electrolysis, collagen work, surgery, fat grafting, implants, filler and simply giving everything time, they have changed enormously. The enlarged pores and roughness I used to notice have pretty much disappeared.

To my eye, if you look closely at my cheeks today, there is nothing particularly unusual about the skin compared with other women my age.

And considering where I started, I’ll take that.

There was never one magic cream or one magic treatment. There were three different problems: laxity, volume and skin quality.

It took me a while to stop asking one treatment to solve another treatment’s problem.

But eventually, bit by bit, we went from a craggy-arsed man with a forehead resembling a topographical map to what I have today.

And one Friday afternoon in Cork, while a small army of synthetic workers quietly got on with writing my code, I sat down and realised that the face I used to spend so much time trying to fix isn’t really a problem I think about very much anymore.

Which is probably as good a result as I could have hoped for.

It’s a Friday afternoon in Cork and my Relay system seems to be ticking over nicely. Code is coming out, workers are working, everyone seems happy, so I thought I’d turn my attention to this.

This is a subject I’ve been asked about quite a lot. I’ve described, in frankly immense amounts of detail, exactly how I transitioned, what surgery I had done, what worked, what didn’t and all the rest of it. But I haven’t really talked very much about what I’ve done to my face apart from the surgery.

And there has been quite a lot.

This isn’t going to be War and Peace. I’m not attempting to write the definitive guide to aesthetic medicine. I’m simply going to tell you what I did, why I did it and roughly what order I did it in.

Because if you walk into almost any skin clinic, for want of a better term, you will be confronted by a gazillion different treatments: microneedling, RF microneedling, fractional lasers, CO2 lasers, Erbium lasers, IPL, BBL, chemical peels, radiofrequency tightening, ultrasound tightening, PRP, skin boosters, fillers, Sculptra, Radiesse, and an endless parade of machines with names like Morpheus8, Potenza, Ultherapy, Thermage and God knows what else.

Half of them sound as though they should either be attacking a small country or appearing in a Marvel film.

Some of these things are genuinely very good. Some might be very good for you, but completely pointless for me.

That is the important bit.

Before spending any money, I think you need to work out what problem you are actually trying to solve.

Three different problems

This is how I eventually came to think about my own face:

Laxity. Volume. Skin quality.

They overlap, obviously, but they are not the same problem.

Laxity is basically how firm everything is. If you’re pushing 40 or 45, there’s a reasonable chance things aren’t quite sitting where they did when you were 25.

Although not always.

I know one trans woman who is 51. I was sitting next to her in a car the other week looking at her face and she has virtually no skin laxity whatsoever.

You bloody cow.

I did.

The mistake I think people make is trying to solve substantial laxity by throwing hundreds and hundreds of pounds or euros at comparatively small treatments.

€500 here.

€600 there.

Another €700 six months later.

None of these things are cheap. They’re just cheap relative to surgery.

There are non-surgical treatments that can tighten skin to a degree, particularly if the problem is fairly mild. But if you have significant facial and neck laxity and want a significant result, you are eventually getting into facelift and neck-lift territory.

Sorry.

I was.

Volume is a completely different problem. I had lost an enormous amount of it. My mid-face was virtually concave when I started.

I’d lost significant amounts of weight twice in my life and done years of endurance cycling, and I had very hollow cheeks. At the time I thought it made me look lean and masculine.

Which, unfortunately, it did.

It just wasn’t remotely what I wanted when I started trying to make my face look female.

Then there is skin quality itself: thickness, texture, pores, pigmentation, fine lines, smoothness, sun damage and that slightly crepey quality skin can acquire as it ages.

So those were my three problems.

And I started attacking them.

The nuclear option

When I first transitioned, before the FFS, before the facelift, before everything else, I sat down and looked at the enormous list of things I could supposedly do to improve the actual quality of my skin.

Then I ranked them.

Sitting at the top was CO2 fractional ablative laser.

This was the hard hitter. Not the pleasant option. Not the lunchtime option. Not the pop in on Thursday and nobody at work will notice option.

This was the one where I effectively had to disappear for the best part of eight or nine days because I came out looking like a burns victim.

It is brutal.

My God, though, it works.

I’ve had it done twice. More on round two later.

The first time I had my whole face done, my neck and even my eyelids, and I had absolutely no idea what I was letting myself in for.

They put me on a bed in the clinic, anaesthetised the area around my eyes, and then inserted these little metal shields underneath my eyelids. Essentially enormous metal contact lenses with tiny handles on them.

Why?

So they could laser my bloody eyelids.

The things I will do for beauty.

The recovery was horrific. For the best part of a week I looked like some sort of monster.

Then it healed.

And the results started appearing.

If somebody said to me, “You get one serious skin-resurfacing treatment. Pick one,” I’d pick this.

It made a massive difference to me.

Where I initially got fillers completely wrong

My first experience with filler and Botox was before transition. I went into a clinic presenting completely as a man.

And almost immediately, something ridiculous happened.

The doctor spotted my Rolex.

Then we somehow got into that peculiar thing men occasionally do where each one starts subtly trying to out-impress the other.

You know the sort of thing.

A little man-off.

And I participated enthusiastically because, apparently, I was an idiot.

I walked out afterwards and thought:

You fucking idiot, Stevie. What are you doing?

Because not only had I walked into an aesthetics clinic presenting as a man, I had then spent part of the consultation performing masculinity with the bloke who was about to inject my face.

Unsurprisingly, he gave me the most masculine filler imaginable. Definition, angles, chiselling. He had looked at the man sitting in front of him and tried to make him into a better-looking man.

Entirely reasonable.

Also precisely the opposite of what I actually wanted.

A few months later, I tried again.

I was still at the stage where I thought filler might be capable of doing quite a lot of the heavy lifting. I already knew I probably needed a facelift eventually, but my mid-face was badly depleted and everything was rather, shall we say, soggy.

I thought perhaps filler could fill it out temporarily while I worked out what I was going to do properly.

This time I went somewhere completely different.

And this time I told her everything.

I was still presenting male when I walked through the door, but I showed her a photograph of Stevie.

She looked at the photograph.

Then she looked at me.

Then back at the photograph.

Her expression basically said:

Who the hell is that?

“That’s me,” I said.

“That’s the other me.”

So I explained.

From that point onwards, everything was aimed at the female face I was trying to create.

We added volume to the cheeks and it helped to a degree, but I was still asking filler to do far too much.

Eventually I realised that.

So I stopped.

Completely.

I decided I would deal with the actual structure first and come back to filler later, if I still needed it.

That turned out to be one of the better decisions I made.

Botox

That second clinic was also where I started doing Botox properly.

In my head, I divide Botox into two types.

The first is ordinary anti-wrinkle Botox: forehead, frown lines, crow’s feet, the usual areas.

Something I didn’t appreciate initially was how cumulative the cosmetic result could be. Obviously the Botox itself starts working quite quickly, but if you already have established expression lines, one round isn’t necessarily going to erase years of creasing.

What happened to me was that repeated treatment stopped me continually folding the same bits of skin in the same places, and over time everything became much smoother.

I have a before-and-after photograph I’ll include here. Both pictures are pre-FFS. No facial surgery whatsoever.

The difference is significant.

Incidentally, the second photograph is also rather poignant for me. It is the very last photograph of me as a man.

I think about a week later, he was gone.

The second type is what I rather unscientifically think of as atrophy Botox.

The obvious example is masseter Botox, where much larger quantities are injected into the muscles at the side of the jaw with the intention of weakening them and, over time, reducing some of their bulk.

If you are trying to feminise a square lower face, you can probably see the attraction.

I did this twice.

The first time was quite funny. I was still living with my family and I think we had steak for dinner that evening.

Oh my God.

My jaw was knackered.

I sat there chewing and chewing and thinking:

For Christ’s sake, why is eating this steak suddenly an endurance sport?

Whether it made a gigantic visual difference to me, I’m not entirely sure.

But I did it.

Twice.

I’ve also done the smaller tricks, like lip-flip Botox.

Chasing collagen

Around all of this I became increasingly interested in collagen.

I started taking hydrolysed collagen every morning, which I’ve now done for years. Am I absolutely convinced it makes a dramatic difference? No. I do it anyway.

More interesting to me was Sculptra.

Sculptra is made from poly-L-lactic acid, or PLLA. Rather than simply behaving like a conventional filler and creating immediate volume, the idea is to stimulate a gradual tissue response and collagen production.

One of its early medical uses was treating facial lipoatrophy in people living with HIV, which immediately caught my attention because, structurally at least, a depleted face was exactly one of the problems I was trying to solve.

So I had Sculptra.

I liked the philosophy of it: rather than endlessly adding more filler, encourage the face to rebuild some structure of its own.

And, by the way, I also microneedle my face every so often.

The structural work

Eventually I had the FFS and facelift.

Initially, everything looked extraordinary.

Partly because the work was extraordinary.

Partly because my face was swollen to approximately the size of Belgium.

As the swelling disappeared, though, it became obvious that I still had a lot of volume depletion through the mid-face.

So I moved on to fat grafting.

I was warned from the outset that I might need several rounds because not everything survives.

I was deeply unimpressed by this information.

I had rather hoped they could put it in once and we could all go home.

But no.

The first round helped a lot, but I still didn’t have the underlying projection and structure I wanted.

So my next trick was...

Cheek implants.

I know.

I am slightly extreme.

Little incisions inside the mouth, solid implants positioned over the cheekbones, and suddenly the soft tissue had something underneath it that had been missing before.

Scaffolding.

That made a substantial difference.

There was still some hollowing lower down, so I had another round of fat grafting.

Again, better.

Much better.

Still not quite there.

And this is where filler finally became brilliant.

Architecture versus finishing work

By this point, the lifting had been done. The implants were in. The fat grafting had restored a lot of the missing volume.

I wasn’t asking filler to rebuild my face anymore.

I was asking it to finish it.

I had filler placed into the medial cheeks and suddenly it worked spectacularly well. That relatively small amount of additional volume filled the remaining hollow and tied everything together.

That was when filler finally made sense to me.

Early on, I had been trying to use filler as architecture.

Later, I used it as finishing work.

And it was vastly better at the second job.

Lips

I’ve also had several rounds of lip filler over the years because I started with virtually no lips whatsoever.

Honestly.

Two little elastic bands attached to the front of my face.

I haven’t gone for gigantic lips. I just wanted enough to give my mouth some actual shape and definition, and it has helped enormously.

These days all of this is much less intensive. I might have a little medial-cheek filler when it needs it, some lip filler perhaps once a year, and Botox roughly every four months in the normal girly bits.

That’s about it.

At this point you’re probably thinking:

Jesus Christ, Stevie. Is there anything you haven’t done?

We haven’t even got to the bathroom cabinet yet.

The bathroom cabinet

At some stage I researched the living hell out of skincare.

My morning routine is actually fairly simple.

I cleanse in the shower. I buy decent cleanser, although I’m not entirely convinced this is an area where anyone needs to spend a fortune. We still have a few irritating little hairs to shave off as well, which is depressing, but we’re getting there.

Every other day or so I use an AHA/BHA exfoliant. At the moment it’s just The Ordinary.

Then hyaluronic acid for hydration and a bit of plumping. I’m currently using Vichy, although again, I doubt you need to spend much money here.

The first thing I really care about is vitamin C. At the moment I’m using La Roche-Posay C12.

Then comes the least glamorous but probably most important part of the whole routine: SPF 50.

Every day, whatever the weather. Even when Ireland is doing that weird thing where it looks as though somebody has placed a grey Tupperware lid over the entire country.

SPF 50.

Then moisturiser.

Done.

Night-time Stevie

In the evening I use a serum. At the moment it’s some Clarins one I got relatively cheaply and, if I’m being completely honest, didn’t research to within an inch of its life.

It feels nice.

That’s about the strength of my scientific conclusion.

Then comes tretinoin.

For me, this is one of the serious parts of the routine.

I now use it almost every night, but I absolutely could not do that when I started.

Oh God, no.

Before I’d even had my facelift, I went through a phase of pushing my luck with it. If I used it too many nights in a row, particularly around the eyes, there would eventually be consequences.

I remember waking up one morning and my skin was flaking, the area beneath one eye had dried up and crinkled, and I looked like Emperor Palpatine from Star Wars.

I stared at myself in the mirror and thought I had finally overcooked it.

So I backed off, started again, backed off, started again, and gradually my skin became much more tolerant of it.

Mine is prescription strength, although I acquired my current mountain of tubes over the counter in Bangkok.

I bought enough to survive a small apocalypse.

At the current rate I should probably make it into 2027.

Then moisturiser.

Bedtime extras

I also have two LED masks, one for my face and one for my neck and upper chest.

Both run for about ten minutes, so I generally use them when I get into bed.

You are imagining me lying there looking like Darth Vader’s high-maintenance sister.

But it’s ten minutes while I’m already doing absolutely nothing, so it doesn’t particularly inconvenience me.

I’ve also just started another experiment: prescription estriol cream on my face twice a week, replacing tretinoin on those nights.

There is some interesting research around topical oestrogens and ageing skin, particularly collagen, thickness and hydration. But there is a fairly enormous difference between interesting research and everyone should smear hormones on their face.

I’m trying it.

That’s all.

Whether it does anything spectacular for my skin remains to be seen.

Ask me in six months.

And finally, the controversial one

Right.

Here we go.

The blue liquid.

GHK-Cu.

Copper peptide.

GHK-Cu is a naturally occurring copper-binding peptide in the body which has attracted quite a lot of interest around tissue repair and skin biology.

You’ll find copper peptides in perfectly ordinary topical skincare products.

That isn’t the controversial bit.

I inject mine.

Daily.

And before anybody starts ordering syringes because Stevie Bennett said so on the internet:

don’t.

Injectable GHK-Cu for cosmetic skin improvement is nowhere near as established as sunscreen, tretinoin or Botox. The evidence base is much thinner and this particular corner of the market can be something of a regulatory Wild West.

I’ve read about it and made my own decision.

That does not make it a recommendation.

The boring things

Beyond all of that, I do the boring things.

I drink a lot of water and have done for twenty-odd years. I don’t sunbathe. I stay out of strong sun where I can. I wear SPF. I generally eat pretty well.

Not perfectly.

I am a human being.

But pretty well.

Day to day, none of this actually feels particularly onerous. Morning skincare takes a few minutes, evening skincare takes a few minutes, and the LED happens while I’m lying in bed. Botox is every few months. Fillers are occasional.

The giant interventions happened over years.

Am I finished?

Not quite.

I still have some electrolysis to finish around my chin and mouth. Once that is finally done, I’m going to reassess the skin in that particular area.

And this is where that second CO2 treatment comes in.

I had another round focused there and, disappointingly, it didn’t make as much difference as I’d hoped.

So there is still some work to do.

The cheeks are a completely different story. Between the resurfacing, electrolysis, collagen work, surgery, fat grafting, implants, filler and simply giving everything time, they have changed enormously. The enlarged pores and roughness I used to notice have pretty much disappeared.

To my eye, if you look closely at my cheeks today, there is nothing particularly unusual about the skin compared with other women my age.

And considering where I started, I’ll take that.

There was never one magic cream or one magic treatment. There were three different problems: laxity, volume and skin quality.

It took me a while to stop asking one treatment to solve another treatment’s problem.

But eventually, bit by bit, we went from a craggy-arsed man with a forehead resembling a topographical map to what I have today.

And one Friday afternoon in Cork, while a small army of synthetic workers quietly got on with writing my code, I sat down and realised that the face I used to spend so much time trying to fix isn’t really a problem I think about very much anymore.

Which is probably as good a result as I could have hoped for.

My evenings tend to start the same way.

Eventually I drag myself away from the screens in my office and start doing all the boring little things that make tomorrow morning slightly less irritating. I prepare my breakfast, put the dishwasher on, make sure the bedroom is tidy and wander around doing jobs I should probably have done earlier.

And then Chester notices the logs.

This is the important bit. The moment I start putting logs on the fire, he knows exactly what is supposed to happen next.

She's going to lie down on the sofa. Excellent. Please lie down on the sofa. Now.

If I make the mistake of wandering back into the kitchen afterwards because I've forgotten something, I can actually see the irritation on his little face. His head starts wobbling from side to side as he watches me.

What are you doing? We had an agreement.

Fire. Sofa. Chihuahua.

Tonight I eventually complied. I lit the fire, lay down and watched the final episode of The Gentlemen on Netflix. Incidentally, was Ray Winstone contractually prohibited from being filmed anywhere other than a sauna for the entire series? Every time he appeared I expected somebody to throw another ladle of water over the rocks.

Anyway.

After that I opened YouTube.

YouTube has become particularly irritating recently because it keeps offering me approximately the same twelve things forever, so for reasons I cannot quite explain, I clicked on my old subscriptions instead.

I haven't looked through them properly in years.

Oh dear God.

I genuinely think I may have one of the most eclectic YouTube subscription lists in existence. Algorithmic crypto traders sitting beside James Charles, programming channels, makeup tutorials, finance and, I'm sorry, Jordan Peterson.

All sitting happily beside each other like the world's most dysfunctional dinner party.

Then I started seeing names from another life. Crypto, Bitcoin, trading, technical analysis. People I used to watch years ago when I spent an unhealthy proportion of my life sitting in front of huge banks of monitors writing trading algorithms.

I wondered how many of them were still going.

So I clicked on Ivan on Tech.

I mainly wanted to hear the introduction because I always found it funny. He used to launch into his videos with this enormous, enthusiastic Eastern European accent and an intensity suggesting Bitcoin had approximately thirty seconds left to live.

I intended to watch for thirty seconds. Two minutes later, I was still there.

And then I started getting annoyed.

Because there it was again. The thing that eventually drove me absolutely insane about retail technical analysis.

Some indicator had changed state. Bitcoin had crossed something called a Bull Flip. A bullish zone. A line had changed colour. And it was being discussed with the solemnity of Moses receiving the tablets.

Apparently this mattered. Apparently Bitcoin had done a Thing.

And I found myself sitting on the sofa thinking something I remember thinking many years ago:

Bitcoin does not know it has crossed your fucking indicator.

It doesn't.

Bitcoin isn't sitting there watching twenty-five TradingView indicators. It hasn't noticed the golden cross. It isn't worried about Ivan's Bull Flip. It doesn't know your RSI has crossed 50.

And unless enough actual market participants are watching exactly the same thing and acting on it, the market doesn't particularly care either.

There are exceptions, obviously. Widely watched levels can become reflexive. If a sufficiently large proportion of participants care about the 200-day moving average, then the 200-day moving average can matter precisely because everybody cares about it.

But some proprietary rainbow-coloured indicator using seventeen transformations of exactly the same price data?

Come on.

I used to call it chart pornography.

And I say that as somebody who spent years producing a considerable amount of chart pornography myself.

My journey into algorithmic trading

I started out like most technically minded people probably do. I discovered Pine Script, looked at other people's scripts, played with strategies, changed parameters and combined indicators.

This one looks good. What happens if I add this? What happens if I change that period from 20 to 25?

Oh, look at that.

Christ, I've cracked it.

Then you get more sophisticated. You stop downloading somebody else's RSI strategy and start building your own things. More complicated mathematics, more data, machine learning, optimisation and different market regimes.

More screens. More code. More cleverness.

And something very peculiar happens. The more you actually build these things, the less impressed you become with them.

Because an indicator can look like absolute voodoo on a chart. Green there, buy. Red there, sell. Green again, buy. Jesus Christ, look at that. It caught the whole move.

Now turn it into an actual automated strategy.

That's where the fun starts.

No repainting. No magically deciding after the candle has closed that you would obviously have entered halfway through it. Trade using the information that genuinely existed when the decision had to be made. Execute on the close, add fees, slippage, the difference between the price TradingView thinks existed and the price your exchange actually offered you, and then add latency.

Add the real world.

And suddenly Mystic Meg has lost quite a lot of her mysticism.

This is why those YouTube videos where somebody puts TradingView into replay mode and manually draws profit boxes on the screen used to drive me demented.

Yep, winner there. Green rectangle. Winner there. Another green rectangle. Tiny little loss. Massive winner. Look how easy this is.

No.

You are manually backtesting your own hindsight.

Of course it looks wonderful. You already know what happened.

And even when you're genuinely automating things, the next monster arrives.

Overfitting.

You produce something that looks spectacular on Bitcoin. Absolutely beautiful equity curve. Sharpe ratio to make your mother proud.

Then you try it on Ethereum and it loses money. Solana loses money. AVAX makes a tiny profit. Change one parameter slightly and the whole thing falls apart. Move the test window six months and suddenly your beautiful strategy looks considerably less beautiful.

Then you optimise it.

Now it works again.

Brilliant.

Except you've potentially just found the exact collection of numbers that most elegantly explains the past. That isn't necessarily prediction. Sometimes it's just curve fitting wearing expensive glasses.

Eventually I became much more interested in robustness than optimisation.

I didn't particularly want something that made 80% on Bitcoin using parameters 17.4, 38.2 and 2.73 but collapsed everywhere else. I'd rather have something that made 10 or 20% reasonably consistently across a basket of assets.

Something that was directionally right. Something where I could jiggle the parameters around and it didn't immediately fall apart.

Because that at least suggested I might have found something resembling a real phenomenon rather than a particularly attractive historical accident.

And writing that kind of algorithm is incredibly fucking difficult.

My algorithms, in the end, were average. Some were decent, some made money and some didn't. None of them contained the secret mathematical key to the markets.

And there is a dangerous temptation when you've built an average strategy. An average strategy doesn't make enough money, so you introduce leverage. Now your average strategy makes exciting money.

Until it doesn't.

I learned that lesson extremely expensively.

The market doesn't care about your lines

Around the same time, my thinking about markets started changing. I became less interested in transformations of price and more interested in information about the system producing the price.

What was global liquidity doing? What was happening in bonds? What was volatility doing, and how did bond volatility affect the transmission of liquidity into risk assets?

I started looking at derivatives markets, CME expiry dates and the pricing of subsequent contracts. I was interested in what changes in the futures curve might tell me about confidence further out, how expectations were evolving and what participants were collectively willing to pay for future exposure.

I was increasingly interested in what I would describe as the wisdom of the crowd.

Not because markets possess some mystical perfect wisdom. They don't. Crowds are frequently idiots. But markets aggregate enormous quantities of information, expectations, incentives and positioning.

And that interested me far more than whether two moving averages had kissed.

I still used moving averages, of course. I used plenty of conventional technical signals, but they increasingly became third-level confirmation. They weren't the thesis.

The thesis came first.

And that distinction eventually became the most important thing I learned.

You have a thesis, and then you collect evidence. Some evidence strengthens it, some weakens it and some changes it entirely. An indicator is one possible piece of that evidence.

It is not divine revelation.

The other problem I hit was the limitation of the tools themselves.

TradingView is fantastic for what it is, but I became increasingly frustrated that I couldn't simply consume whatever external data I wanted directly into my strategies.

I had endless ideas for services I could have written in C#. I wanted to pull data from multiple sources, normalise it, timestamp it properly, create historical series and build my own derived datasets.

I wanted to combine liquidity data with volatility measures and aggregate information that the normal TradingView user simply didn't have access to.

More importantly, I wanted to be able to backtest against those historical datasets properly, without introducing all the usual problems of look-ahead bias and information that wouldn't actually have been available at the time.

That interested me because at least then I was attempting to create an informational advantage.

If everybody has the same OHLCV data, everybody has the same RSI, everybody has the same MACD and everybody has access to the same library of community indicators, exactly where is your edge supposed to be coming from?

You can still create one. Execution can be an edge. Statistical modelling can be an edge. Market microstructure can be an edge.

But the bar is extremely high.

There are firms stuffed full of mathematicians, statisticians, physicists, alternative datasets and extremely expensive computers trying to extract fractions of a percentage point from markets.

And then there's Trevor on YouTube with a purple rectangle.

The retail trading circus

This is the part that actually makes me feel sorry for retail traders.

Because there's an entire industry built around selling certainty.

BUY NOW. BITCOIN ABOUT TO EXPLODE. THIS INDICATOR HAS NEVER BEEN WRONG. THE NEXT 48 HOURS WILL CHANGE EVERYTHING.

And some perfectly ordinary person with a few thousand pounds sees a man sitting in front of twelve monitors talking confidently about bull flips and liquidity zones and thinks:

He knows. He has figured it out.

No.

He may know something. He may even be a competent trader. But YouTube has its own incentives.

Excitement gets clicks. Certainty gets clicks. Fear gets clicks.

"This mildly increases the probability of a positive return over a particular horizon, although confidence intervals remain large" does not make a particularly compelling thumbnail.

And there is an obvious question I've always had about some of these people.

If you possess a repeatable trading system capable of making extraordinary risk-adjusted returns, why exactly are you spending Tuesday afternoon shouting at a webcam trying to get me to use your Binance referral code?

Maybe you're just very generous.

Maybe.

I'm not suggesting that every trading educator on YouTube is a charlatan. There are genuinely knowledgeable people out there, and some produce excellent educational material.

But the extraordinary confidence with which relatively trivial technical observations are presented to retail audiences makes me deeply uncomfortable.

Because there's real money involved.

Somebody is going to watch that video and believe that Bitcoin crossing Ivan's Bull Flip is a meaningful reason to put their savings at risk.

And when it goes wrong, the YouTuber has another video to make tomorrow.

The retail trader has a loss.

The greatest irony of my trading career

The greatest irony of my own trading period is that the serious money I made didn't come from algorithmic trading at all.

It came from investing.

Being directionally right.

I bought WULF, the Bitcoin miner, very early and watched the thesis change as the company moved towards AI infrastructure. I bought at around a dollar and sold roughly 70% of the position around $28. I still have the rest.

I also bought MicroStrategy at what would now be a roughly low-teens split-adjusted price and eventually sold part of that position at around $428.

Those positions made vastly more money for me than years spent trying to make algorithms clever enough to predict the next candle.

And that taught me something uncomfortable.

It is, in many ways, easier to find a strong investment thesis than a strong algorithmic trading thesis.

Not easy. Easier.

A good investment thesis allows you to think about the real world. Technology, capital, incentives, structural change and mispricing.

What happens if this company becomes something different? What happens if the market has misunderstood what this asset represents? What happens if everybody is looking at today while I'm looking at five years from now?

That doesn't mean you're necessarily right. A perfectly reasonable thesis can turn out to be completely wrong, and being right about a company's future doesn't automatically mean you've paid a sensible price for its shares.

But at least you're asking questions about the underlying asset and the world in which it exists.

Algorithmic trading is another beast entirely.

To do it properly, you need to be extremely good at mathematics, statistics and software, but even that isn't enough. You need original ideas, suitable data and relentless scepticism towards your own results.

You need a phenomenon that persists across market regimes, survives realistic transaction costs, works on unseen data and doesn't fall apart the moment you move one parameter slightly.

And you need the humility to realise that the beautiful thing you've just created may simply be an exquisitely engineered explanation of yesterday.

There are really two ends of this world that I respect.

Serious quantitative trading at one end and serious thesis-driven investing at the other.

Both require thought. Both require discipline. Both can still make you look like an idiot.

What increasingly irritates me is the enormous pseudo-quantitative swamp sitting between them.

Lots of lines, lots of colours, lots of complicated terminology and lots of confidence. Very little examination of whether any of it actually survives contact with reality.

And when the strategy stops working, rather than questioning the original thesis, somebody simply adds another indicator.

Another moving average. Another confirmation. Another filter.

Eventually the chart resembles the flight deck of a 747.

And what have you really learned?

Quite often, absolutely fuck all.

Back to the sofa

So tonight I watched Ivan for a little while longer than I intended, and then I switched him off.

Chester was asleep beside me. The fire was still going, and I found myself thinking about that enormous desk upstairs.

The same desk that now spends its days covered in AI agents writing software for me was once covered in trading algorithms, blinking charts and strategies trying desperately to predict markets.

I spent years trying to teach computers how to trade.

In the end, the computers taught me something much more useful.

If your idea isn't very good, automating it merely allows you to be wrong with extraordinary efficiency.

Well, well, well.

Apparently I am now established.

A few days ago I did an interview for Heroines of My Life, Monica’s transgender blog, which has been running for about ten years. There are hundreds of transgender women on there. I searched for a few women I remembered from years ago, women whose transitions had inspired me when I was still standing on the other side wondering whether any of this was actually possible.

There they were.

And from 15 September, apparently, there I will be too.

So. I’ve arrived.

Sort of.

This isn’t actually an article about that, although if Monica lets me, I’ll publish the interview here too.

This is the article I’ve been trying to write for nearly a year and have made a complete arse of about four times.

At one point, while recovering from bottom surgery, I tried to write about why I had gone to Thailand and how I had chosen surgeons. Then I started another article about how to assess different surgical options. Then, even worse, about nine months ago I started writing an incredibly arrogant article about how to transition successfully.

Dear God.

I had theories. I had frameworks. I had sections about embodied femininity. I had more frameworks. I had basically decided that, having transitioned for about five minutes, I had somehow reverse-engineered the entire subject.

I found it recently.

Slightly embarrassing.

So let me be clearer about what this one is.

This is a guide to what I did for my transition.

That’s it.

It is not a guide to what you should do. I’m not saying this was the optimal transition, or the safest, or the cheapest, or the most sensible, or the most emotionally enlightened.

It is simply the sequence of things I did, why I did them, what I was thinking at the time, and what I think about those decisions now.

That distinction matters to me because my thinking has changed.

I used to have this blueprint idea in my head: this is how you do it efficiently, this is the correct order, why on earth wouldn’t everybody do roughly what I did?

I don’t think that anymore.

People have different bodies, faces, finances, families, health, appetites for risk, dysphoria, ambitions and definitions of what a successful transition even means.

So this is mine.

Besides, I’ve learned something else over the last couple of years. Transgender people occasionally ask me for advice, I give it, and then they bloody ignore me anyway.

Probably for the best.

I ran it like a military operation

I have said before that I treated my transition like a military operation.

That sounds more dramatic than it was, but fundamentally it is true.

I had a fairly definite aesthetic idea in my head of where I wanted to end up, and I worked backwards from it.

I used a piece of software called Kanban Flow.

Every week I would rearrange the priorities.

What is number one?

What is number two?

What is number three?

What actual things am I doing this week?

At the beginning, the objectives were enormous.

Lose weight.

Sort out my skin.

Deal with facial hair.

Sort out my body.

Sort out my face.

Sort out my voice.

There was always something sitting at the top of the board demanding attention.

I still use the same system now.

The funny thing is that the board has gradually become much more boring.

Voice rehabilitation.

Finish facial electrolysis.

Skin treatments.

Possibly RibXcar.

General maintenance.

I think that is probably progress.

At the beginning, though, I had a visual target.

There were five or six transgender women around my age whose transitions had made a huge impression on me. Most of them have disappeared from public view now and I won’t name them. One who is still very public is Victoria Perera.

What struck me about these women was not simply that they had had good surgery.

They looked like women.

More than that, they seemed to understand how to look like women.

That was what I wanted.

Good face. Good skin. Good brows. Good makeup. Good clothes. Good mannerisms. Good surgery.

Not young. Not some Instagram fantasy of being 23 again.

I was in my fifties.

I wanted to look like an attractive, elegant middle-aged woman.

And I’m not going to pretend attractiveness didn’t matter.

It mattered enormously.

Passing mattered too, obviously, but I did not want merely to cross some technical gender threshold while hating what I saw in the mirror.

I wanted to look good.

That was always part of it.

The thing I hid underneath all the planning

Looking back at the organisation, the dates and the way I moved from one thing to the next, I probably look far more confident than I actually was.

I wasn’t confident at all.

I was terrified.

I have videos from early transition where I used my webcam almost like a confessional diary. I look back at some of them now and find them heartbreaking.

There is one from February 2025 that I have watched perhaps a hundred times.

I am sitting in my office and I say something like this:

In two years’ time, I want to be walking down Oliver Plunkett Street in Cork, with my earrings on, wearing a nice coat, heading back to my Range Rover Evoque.

Someone will look at me and say to her friend:

“Is that woman transgender?”

And the friend will say:

“Yes. I think so. I’m not sure. But she looks all right, doesn’t she?”

And I say:

That’s my dream.

Then I joke that what will probably really happen is people will look at me and think I look ridiculous.

That was where my expectations genuinely were.

Not stealth.

Not perfection.

Not some fantasy where nobody would ever know.

I hoped I might look like a reasonably attractive trans woman who made people hesitate for a moment.

I was scared I was about to throw my entire life away and end up looking awful.

And despite all the planning, I don’t think I properly started believing this could work until June or July 2025.

There is another video from around July where I am sitting in my office cutting between footage of myself then and an old video of myself as a man.

I am laughing.

Actually giggling.

“I cannot believe how much I’ve changed.”

I think that was the point where my internal narrative shifted from:

God, I hope this works.

to:

I think we can do this.

January 2025: the nuclear option

Before the major surgeries, there was skin.

My skin was pretty poor around my face.

I had acne pitting around my chin, old shaving damage, texture problems and generally forty years’ worth of evidence that somebody had been dragging a razor around my face.

I had already been having Botox and fillers for a few months, and my cosmetic doctor told me that the nuclear option for the skin was fully ablative CO₂ laser.

I had it done on 11 January 2025.

I would love to show you the pictures.

I am not going to.

I looked like an actual monster.

Not slightly pink.

Not a bit swollen.

A monster.

For about a week I hid in the house.

When I had to do the school run I put on sunglasses and a woolly hat and tried to move through society without frightening children.

It was brutal.

It also made a massive difference.

A few months later I started doing Sculptra and eventually had roughly four or five sessions.

In February I started Botox into my masseter muscles to reduce the bulk of the jaw muscles. I had it done again around July.

I remember turning up at my cosmetic doctor armed with an enormous amount of ChatGPT-assisted research into transgender Botox techniques.

She looked at me as if she had accidentally booked an escaped medical researcher.

I have also had filler in the medial cheek to soften some remaining hollowness, a couple of millilitres in my lips because nature had given me practically none, and the usual Botox every few months.

In February 2026 I did another round of CO₂ laser, mainly on my chin.

That one disappointed me.

The first treatment made a huge difference.

The second one seemed to do remarkably little.

My chin is still one of the things I am not entirely happy with.

Which may already tell you something about the nature of all this.

The goalposts do move.

The face was the big one

Nothing mattered to me as much as my face.

Nothing.

Not bottom surgery.

Not breasts.

Not my voice.

The face was easily the most important thing.

I had spent months playing with AI and trying to create realistic approximations of what I might look like after surgery. I studied other women. I studied foreheads, jaws, chins and noses until I could probably have sat an exam in facial geometry.

The strange thing is that, initially, I deliberately chose not to make FFS my first major operation.

There was a period early on when I still genuinely believed I could save my marriage.

So I started by speaking to ordinary cosmetic surgeons about a facelift, neck lift and rhinoplasty.

My idea was that I could do those first, sit with the result for perhaps a year, try not to make things any more difficult at home, and then maybe come back later for the forehead, chin, jaw and bone work.

In March 2025 I went to see Facial Team in Spain and explained this.

I effectively told them:

“I know this is completely arse-about-tit surgically, but I have personal reasons.”

They thought it was arse-about-tit too.

They were right.

I was trying to organise surgery around preserving something in my personal life.

By May, I knew my marriage was over.

And once I accepted that, my entire strategy changed.

The question stopped being:

How do I make this easier for everybody around me?

and became:

If I am doing this, what actually gives me the best chance of the result I want?

Facial Team remained my likely choice for perhaps another couple of months.

There were things I liked about them.

But I became increasingly uneasy about the aesthetic direction.

I went through their website looking particularly at older women.

I kept seeing phrases like:

“natural result”

“subtle”

“not overdone”

And during consultation I repeatedly heard versions of:

“You need to be realistic about what can be achieved at your age.”

Now, they did not literally say:

“Be realistic, love, you’re an old bag.”

But that was increasingly how it felt to me.

And my brief was quite specific.

I said:

I want to look like a woman over 50 who has had a bit of work done.

I didn’t particularly care if somebody could tell I’d had cosmetic surgery.

I cared whether it was good cosmetic surgery.

Those are not the same thing.

How do you choose a surgeon?

This became one of the harder questions.

Initially, I put enormous weight on before-and-after photographs.

Then I started thinking about what those photographs actually mean.

Imagine a surgeon performs a thousand FFS procedures.

There will almost certainly be five spectacular results.

Those five will be on the website.

What I actually wanted to know was:

What does the median result look like?

And, even more specifically:

What happens to someone my age, with my starting face, my skin, my bone structure and my particular problems?

That is almost impossible to know.

The ideal experiment would be to take a hundred sets of identical transgender twins, send them to different surgeons and compare the results.

Sadly, this research design appears to have some ethical shortcomings.

So over time I relied on two things:

before-and-after photographs, and personal recommendation.

Photographs told me whether a surgeon was capable of producing an aesthetic I liked.

Recommendation gradually became more important.

Several of the women whose results had originally made me believe transition could work at my age had been treated by Jordan Deschamps-Braly.

Eventually I thought:

Why am I gravitating towards Spain because it is convenient when the results I actually admire seem to be coming out of San Francisco?

June 2025: Turkey first

Before I got to San Francisco, however, an opportunity opened up to deal with my body.

Years earlier I had gained a lot of weight and later lost it. I was left with poor skin around my abdomen that was never going to disappear through diet or exercise.

So the core procedure was a tummy tuck.

My theory at this stage was very simple:

If I am going under general anaesthetic, I want to get as much useful work done as reasonably possible.

So I added lipo 360.

And a Brazilian butt lift.

Because who doesn’t want one of those?

I was also very tempted to have breast implants done at the same time.

Right until the last few days, I was considering it.

Again, I held back because of family circumstances. I thought coming home having visibly altered absolutely everything at once was perhaps a little much.

With hindsight, I probably would have done the breasts in that operation too.

The surgery was scheduled for 6 June 2025.

I went in, stripped off, stood naked while the surgeon and his assistant drew circles and arrows over me showing where they were going to remove fat, cut skin and inject fat.

They kept pointing at different bits of me and saying:

“Not much fat.”

“Not much fat.”

“Not much fat.”

Probably the nicest insult I have ever received.

Then I went into theatre.

I was strapped down.

Anaesthetic.

And then I woke up.

Nothing hurt.

Nothing had happened.

There was a cardiologist there. The anaesthetist. Other people. Somebody translating.

They told me they had aborted the operation because my heart rate had dropped badly under the anaesthetic.

After they left, I burst into tears.

My first thought was:

That’s it. I’ve half-transitioned myself and now I’m stuck.

I thought maybe I simply could not tolerate general anaesthesia.

And within minutes I started bargaining with myself.

It’s all right.

I don’t look that bad.

I can live with this.

It could be worse.

There was an added reason I was terrified.

I had previously had Graves’ disease. My heart had misbehaved in the past and had gone into AFib a couple of times. I had failed an ECG before.

So cardiac testing scared the living daylights out of me.

They put me on a 24-hour ECG.

Then they put me on a treadmill with another ECG connected and gradually increased the speed.

I was pretty fit at the time.

They turned it up.

I said:

“Higher.”

They turned it up again.

“Higher.”

Eventually they stopped.

“That’ll do.”

“I could have gone much higher than that.”

Apparently even terror does not entirely suppress my competitive instincts.

The cardiologist eventually came back and told me my heart was healthy.

The problem was how my heart rate had responded to that particular anaesthetic approach.

They could alter the protocol.

All systems go.

The relief was enormous.

On 7 June, they performed the surgery.

When I woke up properly after the tummy tuck, I discovered something else.

Pain.

Christ alive.

It felt like somebody had shot me through the stomach.

I remember basically shouting:

“Morphine. Morphine.”

Somebody came along, gave me some, and the modern pharmaceutical industry restored order remarkably quickly.

The first three days were fairly rough.

Then it improved much faster than I expected.

About two weeks after I came home, I put on something I called my benchmark dress.

It was a fake pleather bodycon dress.

Not something I intended to wander around Cork wearing.

It existed almost as a measuring device.

I still had post-operative leggings on underneath.

I put it on, stood in front of the mirror and took a photograph.

And I remember thinking:

Holy fuck. I look like a woman.

That was the moment.

Not “my waist looks better”.

Not “this surgery has worked”.

It was the first time I looked at the complete silhouette and thought:

That is unmistakably female.

The hotel in Turkey was almost worth an article of its own.

It was included in the surgical package and seemed to be populated almost entirely by men recovering from hair transplants and women recovering from mummy makeovers.

We all shuffled around with drains hanging out of us, nodding politely at each other.

A sort of international cosmetic-surgery veterans’ association.

The whole operation was under €10,000.

For that particular group of body procedures, Turkey made sense to me because it was a huge, high-volume cosmetic-surgery market and this kind of work was routine there.

2 August: San Francisco

On 2 August I flew to San Francisco to consult Jordan Deschamps-Braly.

I stayed at the Taj Hotel beside his office.

The barman and I got talking.

“He comes in here.”

“What do you mean?”

“His name is on the bar.”

I walked over.

There was a bloody plaque with Jordan Deschamps-Braly’s name on it.

Then one day, while I was sitting there, he walked in.

The barman gave me a little wink.

So I went over.

Jordan looked at me.

“Who the hell are you?”

“I’m tomorrow’s patient. I’ll see you then.”

He was lovely.

I liked him enormously.

He had some connection with Manchester and knew an alarming number of English and Northern English expressions, which was quite funny coming from a Californian surgeon.

I was impressed.

I paid my deposit.

I was ready to proceed.

Then Thailand appeared.

Someone whose opinion I trusted in transgender medicine said to me:

“He is very good. But I don’t send my patients to him. I send them to this surgeon in Thailand.”

That threw everything up in the air.

I did not have the same volume of before-and-after photographs.

It was not about cost.

I trusted the recommendation.

There was another factor.

Other surgeons had told me the facelift and neck lift would need to be separated from the skeletal FFS work.

The surgeon in Thailand was prepared to combine them.

He was also prepared to do my breast augmentation at the same time.

For someone trying to compress the surgical phase into as few anaesthetics and recoveries as possible, that mattered.

So, at the last minute, I changed course.

7 and 8 September: seventeen hours

I flew to Thailand on 7 September.

The operation was too large to perform in a single day.

It became roughly 17 hours of surgery across two consecutive days.

Day one:

• breast augmentation

• lip lift

• tracheal shave

• open rhinoplasty

The nose was a major reconstruction.

They harvested rib cartilage, opened the whole thing and rebuilt it.

Then I woke up knowing that the following morning I was going back under.

And day two was the bigger one.

• Type III forehead reconstruction

• titanium plate

• facial fat grafting

• genioplasty

• jaw work

• deep-plane facelift

• neck lift

I have scars running behind my ears, around them, across my forehead and down the other side.

If you joined everything together at the back, you could probably peel the skin off my entire head.

That recovery was the hardest of the lot.

Not vaginoplasty.

FFS.

Simply because of the sheer volume of surgery.

I needed ice packs constantly.

I was swollen, bruised and absolutely battered.

But psychologically I dealt with surgery surprisingly well.

I approached it in much the same way I used to approach triathlon or endurance sport.

This part is going to be horrible.

Fine.

It ends.

Get through it.

By the time I reached voice surgery months later, the whole theatre ritual had become almost familiar.

Here we go.

Anaesthetist.

Hello boys.

Surgeon.

Nice to meet you.

Let’s do this thing.

Seeing my face

I stayed in Thailand for a month after the facial surgery.

For much of that time I looked as though I had been attacked by agricultural machinery.

But even very early on, there were glimpses.

There is a photograph of me in a bikini only seven or eight days after surgery.

I was still bruised and swollen.

And even then I remember looking at it and thinking:

Jesus Christ.

I look like a woman.

Then, towards the end of my stay, the clinic offered to take me to a makeup artist.

The idea was to disguise the remaining bruising and let me see the face underneath properly.

I cannot imagine many clinics in the West offering that.

Obviously I said yes.

She did the makeup.

I looked in the mirror.

And for the first time I could really see it.

The strange thing is that psychologically I accepted the new face almost immediately.

Within a couple of weeks it simply felt like mine.

The physical settling took vastly longer.

The forehead came in relatively quickly.

The chin took months.

The skin around the jaw and neck kept changing.

And the nose took the longest of all.

The tip gradually lifted and refined itself over months.

I used to look at it and think:

I’m not sure.

Now I actually quite like it.

If I compare photographs from one month after surgery with photographs now, the difference is enormous.

At the time I thought the one-month result looked wonderful.

Now I look back and think:

Oh dear.

I had a chin like Bo’ Selecta.

That is one of the stranger things about facial surgery.

A couple of millimetres here or there make an enormous visual difference.

At one month I now see swelling.

At one year I see my face.

And the part I love most surprised me.

My eyes.

I never particularly thought:

I hope I end up with lovely eyes.

But they are my favourite thing now.

I think they look natural.

I think they look feminine.

I like them.

I never expected that.

There are still things I would change.

I wish my nose were slightly smaller.

The surgeon explained that he could potentially have reduced it further, but that he was concerned about function.

I would rather be able to breathe, thank you.

I wish my chin were fractionally smaller.

I wish the facelift had been slightly tighter.

But these are now refinements, not catastrophes.

11 January: while you’re in there…

Four months later, on 11 January 2026, I went back to Thailand for vaginoplasty.

I have already written quite a lot about that:

So I am not going to reproduce the entire story here.

But I did continue my slightly deranged habit of asking:

If I am already under anaesthetic, is there anything else useful we can do?

My mid-face was still slightly hollow after the original fat grafting.

Jordan Deschamps-Braly had actually told me that facial fat grafting often required more than one round because not all of it survives.

So, while I was having vaginoplasty, I added cheek implants.

And some upper-back liposuction.

Because apparently I am incapable of booking a single-purpose anaesthetic.

I also asked about a leg lift.

The surgeon said no.

There are limits.

A leg lift and vaginoplasty put too much surgical tension and too many wounds in the same area.

So that one stayed off the list.

The vaginoplasty recovery itself was surprisingly manageable.

I had an epidural, which helped enormously.

What I did notice by then was the cumulative effect of all this surgery.

I had compressed a huge amount of physical trauma into a short period.

My exercise routine repeatedly disappeared because every time I started to recover and train properly again, another operation arrived.

I seemed to get ill more easily.

I had colds and flu more often.

I developed some horrible nerve and shoulder pain after vaginoplasty and had a few episodes of back trouble. I suspect some of that may have been connected to long periods immobilised on operating tables, although that is only my theory.

There was a physical cost to doing everything quickly.

Would I therefore conclude that I should have slowed down?

No.

That may be the lesson some people expect me to have learned, but it isn’t mine.

For me, getting through the major surgical phase quickly was still the right decision.

Makeup: the Laura Ashley years

One thing I underestimated massively was how much work goes into presenting yourself the way you want to.

Skin.

Brows.

Makeup.

Clothes.

Exercise.

Treatments.

Maintenance.

It is like painting the Forth Bridge.

You finish one end and immediately discover the other end needs doing again.

When I first started experimenting privately with makeup, I bought some cheap products online and vaguely remembered how I used to do makeup in the 1990s.

I looked like a model from a Laura Ashley catalogue.

I wasn’t completely clueless.

I had worn makeup before.

But modern makeup?

Correct foundation shades?

Not looking dated?

Not looking ridiculous?

I had work to do.

So I watched tutorials.

I experimented.

By April 2025 I would say my makeup was still a bit shit.

By July it was getting better.

Around November I booked a proper lesson.

I was supposed to be there for an hour.

I stayed for nearly three.

I offered to pay extra and she said it had been a pleasure.

She did say I already knew more than she expected, which was nice, but more importantly she taught me a lot.

Then a friend recommended another makeup artist, so I booked her too.

Again, I learned more.

That is basically how the whole thing worked.

Try something.

Get it wrong.

Improve it.

Repeat.

These days I can put on liquid eyeliner without making a complete arse of it.

I regard this as progress.

My two-mode eyebrows

My eyebrows were hilarious.

Even before I was fully out, while I was still sometimes presenting as male, they were already becoming suspiciously well shaped.

I had two eyebrow pencils.

One for female presentation.

One for male presentation.

If I was going out as myself, I would emphasise the arch.

If I was going out in male mode, I would literally colour the arch back in to make the eyebrow look less shaped.

A kind of eyebrow witness-protection programme.

The funny thing is that almost nobody noticed.

My wife occasionally did.

She would look at me and say something like:

“Jesus Christ, the state of your eyebrows.”

But somehow I mostly got away with it.

Three wardrobes

Clothes also went through phases.

I effectively have three generations of wardrobe.

The first is the pre-coming-out stuff, much of which I don’t particularly like anymore.

Then came the emergency wardrobe.

I suddenly needed enough women’s clothes to actually function, so we hit Shein hard.

Cheap dresses.

Cheap tops.

Experiments.

Some worked.

Some very much did not.

Then, gradually, my actual style developed.

I think that is inevitable.

You buy too much.

You try things.

You discover that something you loved six months earlier now makes you wonder what on earth you were thinking.

Eventually it starts to sort itself out.

I generally knew the direction I wanted to go in from the start.

Not theatrical femininity.

Not costume.

Just an attractive, fairly elegant woman in her fifties.

One problem disappears, another becomes louder

One thing I noticed repeatedly during transition was that whatever bothered me most would dominate everything.

Then I would deal with it.

And almost immediately something else would move to the top of the list.

Initially, the face was everything.

Nothing else came close.

Then the face was done.

And suddenly my attention moved elsewhere.

I would look at myself without clothes and think:

Christ.

This configuration now looks a little bit like a porn star.

There are trans women who are completely comfortable with that.

Fine.

I wasn’t.

So bottom surgery moved up the list.

Then bottom surgery was done.

And what was left?

The voice.

I don’t think the goalposts ever completely stop moving.

What changes is the urgency.

Earlier things felt like:

I need to fix this.

Now something like RibXcar feels like:

That would be nice.

Quite a difference.

The voice

Originally, I genuinely hoped I would avoid voice surgery.

I worked with Seattle Voice Lab.

I practised.

I tried.

I got frustrated.

And I became disappointed in myself.

I thought I was just bad at it.

By around March or April 2026, I had begun thinking:

I am probably going to have to operate on this.

Later it turned out that I had an unusual congenital problem in my larynx and extremely abnormal airflow characteristics.

That changed how I looked back on the whole thing.

I had spent months thinking I was failing at something that, anatomically, was going to be unusually difficult for me in the first place.

I have written separately about choosing VFSRAC and going to Yeson in Seoul:

The surgery was on 15 July 2026.

Physically, compared with everything else?

Nothing.

A walk in the park.

I was discharged the same day.

The hard part was the silence afterwards and the slow recovery.

What shocked me came later.

I played a video recently that I had recorded the day before surgery.

Oh my God.

My voice sounded so male.

I had not understood quite how male it sounded.

What should have told me was the reaction I used to get in public.

I would walk up to a counter.

Someone would greet me normally.

Then I would speak.

And I could see the tiny flicker of recognition.

Oh. You’re transgender.

When I was completely mute after surgery, that stopped happening.

Which was a fairly useful accidental experiment.

Now I am speaking again.

And increasingly, that reaction does not appear to be coming back.

Yesterday was the first day where the voice came out of my mouth almost exactly the way I had hoped it eventually would.

Softer.

Sweeter.

Not forced.

And I thought:

Wow. I think we’re getting there.

What would I actually change?

The obvious retrospective lesson would be:

You moved too quickly.

Slow down.

Take your time.

Spend years finding yourself.

Oddly, that is not my conclusion.

For me, moving quickly was one of the decisions I would make again.

There are things I would change.

I might have done the face before the body surgery because the face mattered more to me than anything else.

Although, ironically, doing the tummy tuck first may actually have helped the overall schedule because I needed recovery time before vaginoplasty anyway.

I probably would have added breast augmentation to that first Turkish operation.

I would probably have booked the voice surgery earlier.

I might have asked for the facelift to be slightly tighter.

These are details.

What strikes me more when I look back is how modest my original expectations were.

I genuinely believed that perhaps, after all this, strangers would look at me and think:

Yes, probably transgender.

But she looks all right.

That was my dream.

The outcome exceeded that dream.

I’m allowed to be pleased about that without pretending it means there is some universal formula behind it.

The thing I thought I would have to learn

Another thing I got wrong was mannerisms.

I genuinely assumed I would have to learn how to move like a woman.

How to sit.

How to gesture.

How to hold myself.

Somewhere in my head, I had created another entire training programme.

Then I started watching myself on video.

And realised:

Oh.

A lot of it is already there.

That was one of the stranger discoveries.

I had expected femininity to involve much more conscious performance than it actually did for me.

Instead, quite a lot of what I thought I would have to construct simply appeared once I stopped suppressing it.

Money

There is an important caveat to everything I have written here.

I had a financial advantage that many people do not have.

Cost did not dictate my choice of surgeon.

That obviously changes the available options enormously.

And even with that advantage, transition cost an astonishing amount of money.

I have never added it up.

I don’t want to add it up.

It isn’t only surgery.

Flights.

Hotels.

Consultations.

Clothes.

Makeup.

Laser.

Electrolysis.

Skin.

Treatments.

Everything.

It is a bloody fortune.

I would prefer not to know the number.

The other cost

The financial cost was not the most important one.

My transition cost me almost everybody in my life.

I had to start again.

Some relationships are slowly rebuilding.

Some are not.

There are people who were once extremely close to me who have never come back and may never come back.

That belongs in any honest account of what happened.

I don’t want to turn this article into an analysis of those relationships, so I will leave it there.

When transition stopped being the main project

Something changed around March this year.

Transition stopped being the main thing in my life.

Not because there was nothing left to do.

It just lost first place.

And what replaced it?

Work.

Obviously.

The crazy bitch who works fourteen hours a day came back.

Technology.

Software.

Learning.

Building.

Ideas.

Trying to understand things nobody has asked me to understand.

I basically moved from one obsession to another.

And strangely, that made me realise how much of me had stayed exactly the same.

All the things I genuinely liked about myself before transition were still there.

Technology.

Finance.

Exercise.

Learning.

Improving myself.

Building things.

The difference was that I was calmer.

Less angry at the world.

I used to spend an enormous amount of time trying to understand everything outside myself.

Politics.

People.

Systems.

The entire bloody universe.

Looking outward, perhaps partly because it stopped me looking inward.

I don’t do that nearly as much now.

I am also less interested in material accumulation.

I still have ridiculous ambition about doing things.

Achievement still matters enormously to me.

But bigger house, bigger car, bigger everything?

Not so much.

The idea of living in an enormous house now sounds exhausting.

Five bathrooms?

Why?

I’ll have one, thank you very much.

In some strange way, transition did not destroy the person I had been.

It made me a happy Stephen David Bennett.

That sentence probably sounds odd.

But it is what I mean.

Same person.

Much more peaceful.

Age

I also want to look young.

There.

Like practically every other woman, I would quite like time to stop attacking my face.

I was never under any illusion that I was going to transition in my fifties and emerge looking 25.

But I absolutely wanted to look good for my age.

Hormones changed things.

Skin treatments changed things.

The facelift changed things.

Fat grafting changed things.

The whole face changed things.

If somebody asks me what my anti-ageing secret is, I do not pretend it is green juice and positive thinking.

My standard answer is:

Seventeen hours of plastic surgery.

RibXcar

There is one more thing I am considering.

RibXcar.

I am speaking to a surgeon in Poland on 9 Octobe

r

Do I need it?

No.

That is the difference.

The face felt urgent.

Bottom surgery became urgent.

The voice felt urgent.

Rib surgery does not.

It sits in a completely different category.

Nice to have.

I just want to look fucking snatched.

That, more than anything, is probably how I know I am approaching the end.

I may have another facelift when I am in my early sixties.

The first one was done alongside enormous skeletal changes, so there was always going to be an element of judgement about how aggressively to tighten everything before all the swelling had settled and the bones had found their final position.

If I have another one later, I would not really count that as transition.

That is just ordinary vanity.

Gravity can still fuck off.

One year later

Yesterday was the first anniversary of the second and biggest day of my facial surgery.

One year.

And a huge amount has happened since then.

My face has finally settled.

My voice is beginning to arrive.

The enormous items on the Kanban board have mostly disappeared.

My work has taken over my brain again.

I am about to appear on Heroines of My Life, which still feels faintly surreal given that I once looked at women on sites like that and wondered whether I could ever get anywhere close.

And yet there is one thing that has not happened as quickly as I thought it would.

Last week I recorded another video.

In it, I said something like:

I cannot fucking believe how often the word transgender still appears in my day.

Still.

In conversations.

In my thoughts.

In things I read.

In things I write.

In the way I analyse myself.

I thought that by now it would have faded further into the background.

It hasn’t.

Not yet.

And I cannot wait for it to.

Not because I am ashamed of being transgender.

Not because I want to rewrite my history.

I just don’t want it to remain the organising principle of my life.

Maybe transition doesn’t end with the final operation.

Maybe it doesn’t end when your face settles.

Maybe it doesn’t end when your voice changes.

Maybe it ends on some utterly unremarkable Tuesday when you suddenly realise:

I haven’t thought about being transgender for a day.

I think I would like that.

Until then, there is still some electrolysis.

A voice to finish rehabilitating.

Possibly some ribs to rearrange.

And, finally, rather more life than transition to get on with.

Another day, another germination of an uncomfortable thought.

It is almost Pride month again.

Pre-transition Steve used to look at Pride month and roll his eyes so hard they nearly detached from his skull.

I remember looking at Regent Street covered in Pride flags and thinking the Third Reich had moved back in, only this time in glorious Technicolor.

“The whole bloody month? Are you serious?”

That really was my attitude.

And if I am being completely honest, part of the reason I resisted transition for so long was because I had a profoundly uneasy relationship with the idea of being “in the LGBT”.

I still remember the day, in front of the mirror in my office, and I started repeating the words over and over to myself.

“I am transgender.”

Again.

“I am transgender.”

Again.

“I am transgender.”

Acceptance was hard.

Discovery was not hard. I had known for decades in the strange submerged way trans people often know things long before they admit them. But acceptance was another matter entirely.

The words felt radioactive.

Then, later, sat in front of my computer, something else hit me and I burst out laughing.

“Oh my God.”

“I’m in the LGBT.”

“What the actual fuck?”

I, Stephen Bennett, was in the LGBT.

This came as a considerable shock to Stephen Bennett.

You see, I had spent most of my life psychologically standing outside all of that.

I would see Pride marches and sometimes recoil from them. I would see leather outfits, gimp masks, fetish aesthetics, public sexuality, rainbow hair, shouting, slogans, and what looked to me like social chaos. And my reaction, if I am honest, was often something between discomfort and embarrassment.

Part of that was probably straightforward prejudice. Some of it was social conditioning. Some of it was class instinct. Some of it was fear.

But a large part of it, I now realise, was that I did not want any of it to have anything to do with me.

Because if those people belonged to the same category as me, then suddenly my problem stopped being abstract.

It became personal.

I also think I had a very specific discomfort with overt sexuality in public. I am actually quite prudy. I always joked about this in my early transition videos. Somewhere inside me there lives a slightly horrified 1970s school prefect and a small amount of Mary Whitehouse.

I do not like public sexual theatrics, regardless of who is doing them.

But here is the interesting contradiction.

At the exact same time as I was rolling my eyes at parts of queer culture, I secretly envied the living hell out of some of it.

Growing up in Britain in the 1970s and 80s, I absolutely loved those funny, cheeky, camp public figures who everyone knew were gay but nobody officially said were gay. Men like Kenneth Williams. Later people like Graham Norton and Alan Carr.

I loved the freedom of it.

The wit.

The looseness.

The theatricality.

The escape from rigid masculinity.

I wanted to sit at that table.

Not because I wanted public sex or fetish parades or slogans.

I wanted the release valve.

I noticed something throughout my life. Whenever I spent time around very camp gay men, if I trusted them, something in me relaxed. My guard dropped. I became softer. More honest. Less frightened.

Back in the 1990s, one of the very few people I ever came out to was a gay couple I knew in Nottingham. They gave me some dresses. I was eternally grateful for that.

That sounds like such a small thing, but it mattered enormously.

Around straight men, especially in the world I grew up in, there were invisible walls around masculinity. You did not admit softness. You did not admit femininity. You certainly did not admit wanting to be a woman.

But with certain gay men, the walls briefly disappeared.

They disarmed me.

I could breathe.

And then something else happened recently.

I was in Boots buying yet more hair nonsense, because transition appears to involve spending the GDP of a small nation on hair products, and there was another trans person in the shop.

Very visibly trans.

Rainbow-coloured hair.

Receding hairline.

Masculine face.

Standing out enormously.

Six months ago, maybe even less, part of me would have looked at that and thought:

“Why would you draw more attention to yourself?”

“If you are already visibly trans, why add rainbow hair on top of it?”

But this time I saw something completely different.

They were not making it worse.

They were taking it back.

And suddenly I understood something I had not properly understood before.

Not everyone survives this by blending in quietly and trying to look as socially acceptable as possible.

Some people survive by becoming louder.

More visible.

More deliberate.

By refusing shame.

And I realised something else too.

My experience of being trans has been easier than some people’s.

I pass reasonably well.

I live a fairly normal life.

I walk around Cork buying makeup and hair products and coffees and nobody really bothers me very much.

And the uncomfortable truth is this:

Part of the reason I get to do that is because other people absorbed the social punishment first.

The flamboyant gay man in 1987.

The activist I rolled my eyes at twenty years ago.

The visibly trans woman walking into Boots anyway.

The people who were prepared to look ridiculous, threatening, embarrassing, political, weird, too loud, too feminine, too obvious, too much.

People suffered so that other people could quietly exist later with less suffering.

That does not mean I suddenly agree with every part of LGBT culture.

I still roll my eyes sometimes.

I still do not naturally think in group identities.

I still dislike ideological conformity.

I still do not trust groups not to colonise individual thought.

I still have a strong instinct toward independence.

And I do not believe being trans automatically makes somebody wise, moral, or correct any more than being straight does.

But I understand something now that I did not understand before.

You do not have to become identical to people to recognise what they carried for you.

And that, I think, is why I now find Pride month oddly moving.

Not because I have suddenly become a perfect Pride person.

God no.

But because I finally understand that I am not standing outside the glass anymore.

I am on the inside now.

Which means when I see irritated middle-aged men rolling their eyes at the flags, I sometimes laugh quietly to myself.

Because I know exactly where they are psychologically.

I used to live there too.

And despite all my instincts toward being a solitary creature, despite all my resistance to group identity, despite all my hesitation around slogans and collective language, I have finally arrived at the conclusion:

We are all in this together, aren’t we?

One of the interesting things about having a Substack and, by the way, we're now getting more than 10,000 article reads a month, which is pretty freaking amazing, so thank you is that you start to notice patterns in the comments.

The same characters keep coming back.

The same arguments. The same insults.

You're a eunuch.

You're a pervert.

You're mutilated.

You're not a woman.

Week after week. Article after article. They return to tell me again.

I had exactly the same thing when I was on X. The same people underneath everything I wrote. Following me around. Waiting for the next opportunity to explain, once again, how revolting or ridiculous transgender people apparently are.

And I've come to a conclusion about some of them.

I think they're fighting with themselves.

I think they're constructing an enormous internal scaffolding of arguments designed to suppress something they absolutely do not want to examine.

I think they're trying to convince themselves that whatever they're feeling, whatever curiosity or recognition keeps dragging them back to this subject, absolutely cannot mean anything about them.

And I think that because I did it.

For years.

I had an enormous history with gender stretching back through my life, and I still spent roughly a decade finding reasons why I couldn't possibly be transgender.

I rationalised. I dismissed. I argued. I built intellectual structures around myself.

Anything rather than open the bloody door.

And here's the clever bit.

If a man simply spent every day obsessively arguing about whether people like me should exist, it would start looking rather peculiar very quickly.

So you need somewhere to hide.

And transgender politics provides some absolutely magnificent hiding places.

Women's rights.

Bathrooms.

Sport.

Children.

Suddenly you're not a man spending hundreds of hours thinking about transgender people.

You're defending women.

You're protecting children.

You're preserving fairness in sport.

You're fighting misogyny.

Perfect.

Now the fixation has a noble purpose.

You can read every article. Watch every video. Study every surgery. Debate every hormone. Examine our bodies. Discuss our genitals. Follow transgender people around the internet and write thousands upon thousands of words about us.

And every time that tiny uncomfortable question appears. Why am I so interested in this? You've already built the answer.

Because you're protecting society.

I don't think that explains everybody who objects to transgender people. Obviously it doesn't.

But the ones who cannot leave it alone?

The ones who return week after week?

The ones who seem to know more about transgender medicine than most transgender people?

The ones who are somehow underneath every article, every photograph, every discussion, endlessly announcing how completely uninterested they are in becoming anything remotely like us?

Those people interest me.

Because I recognise the architecture.

I built it myself.

And eventually mine collapsed.

So, to all my angry male friends who like to spend their time commenting on my Substack:

Come on in, boys. The water's lovely.

Cross the line.

Accept yourself.

You might find you have rather less to be angry about.

I have recently been observing a phenomenon I can only describe as the industrialisation of doing absolutely fuck all.

Not ordinary laziness. We’ve all had a Friday afternoon when the prospect of opening another spreadsheet makes us want to climb into the stationery cupboard and die.

No, this is something far more sophisticated. This is twenty people, all working very hard, all attending meetings, all producing documents, and somehow collectively achieving less than one bloke with a screwdriver.

The easiest way to explain it is with a light bulb. Not a clever one. No Bluetooth. No subscription required to access the illumination functionality. The sort of thing you buy in Tesco.

1. Dave

A large organisation discovers that a light bulb has gone out and engages an electrician. Let’s call him Dave.

Dave arrives on Monday morning. He replaces the bulb, checks the wiring and tests the switch. The light comes on. He turns it off. He turns it on again. Beautiful.

You might imagine that would be the end of the story. You would be spectacularly wrong.

Dave has confused the successful installation of a working light bulb with the successful delivery of the Light Bulb Programme. These are entirely different things.

The Light Bulb Programme has a Programme Board, a Lighting Design Authority, a Risk and Assurance Function, and a gentleman called Martin, the Programme Assurance and Stakeholder Alignment Lead.

Martin’s first job was replacing batteries in emergency torches. He once spent three days investigating a faulty torch before somebody noticed he had put the batteries in backwards. He was promoted to Torch Maintenance Coordinator, where he could supervise battery replacement without going anywhere near a battery.

Twenty years later, Martin is an authority on the governance of illumination.

Martin has concerns.

Martin has not personally produced any light since 2004.

2. The Lighting Design Authority

The Design Authority asks for an architectural diagram. Dave produces one. There are arrows. Everybody likes arrows.

It is circulated to seventeen people, including three on annual leave and one who left the organisation in 2022.

“Dave, could you just talk us through the architecture?”

“Electricity comes in here, passes through the switch and powers the bulb.”

“And the bulb itself?”

“Produces light.”

“Fantastic. Could we capture that in a separate document?”

At the next meeting, Martin asks whether anybody has confirmed that the bulb is compatible with the switch.

“I’ve turned it on and off several times, Martin.”

“Yes, but I think we need to be careful about confusing successful testing with formal confirmation of compatibility.”

The programme manager nods. “That’s a really important distinction.”

Dave briefly considers eating the test report. Instead, he agrees to add a sentence.

Without Martin, the electrician might have walked away under the entirely mistaken impression that turning a light bulb on and off constituted evidence that it could be turned on and off.

3. The forty-document handover

Over the following weeks, Dave produces an Architecture Definition Document, an Interface Definition Document, a Functional Specification, an Operational Support Manual, a Troubleshooting Guide, a document explaining the relationship between the switch and the bulb, another explaining the relationship between the bulb and the room, and a rollback procedure, which consists of turning the switch off.

Forty documents in total.

Martin suggests a simple orientation document explaining what each component does.

“For example, this component called Light Bulb. What does that actually do?”

“It produces light, Martin.”

Dave briefly considers whether prison would really be that bad. Instead, he writes document forty-one:

Light Bulb: The component responsible for producing light.

Light Switch: The component responsible for switching the light on and off.

It reads like GhostDoc, that old Visual Studio extension that generated comments with all the intellectual sophistication of a damp flannel. A property called UserName? The user name. Marvellous.

The document is accepted. The organisation now has a comprehensive understanding of the light bulb.

Unfortunately, the office is still dark.

The Design Authority then asks why the documentation says “light bulb” when the approved terminology is “Illumination Delivery Component”.

Dave changes the heading. Document forty-two.

This is, and I really cannot emphasise this enough, a fucking light bulb.

4. This is enterprise lighting, Dave

Eventually, Dave says it out loud.

“Look, it’s a fucking light bulb. Can we please just turn the bloody thing on?”

The room goes quiet.

“Dave, I appreciate you may be used to smaller domestic installations, but this is a large professional enterprise. We have processes, stakeholders and security requirements. It’s a rather different level of complexity.”

Martin nods. “Enterprise lighting operates at a completely different level.”

Now, before this engagement, Dave had been lead electrical engineer on some of the largest commercial buildings in Britain. Skyscrapers. Hospitals. Substations, backup generators, thousands of circuits. On those projects, fitting a single bulb was a task for the most junior apprentice, possibly as a reward for identifying which end of the screwdriver to hold.

He had not expected to be lectured on enterprise electrical engineering by a man whose principal technical achievement was connecting his laptop to the projector, with assurance provided by a man once defeated by a torch.

Dave considers explaining this. Then he looks at Martin, who is making a note about stakeholder alignment, and decides life is too short.

“Fair enough. You tell me how you’d like it installed.”

“Excellent. That’s exactly the collaborative approach we need.”

5. The Great Switch Access Crisis

The programme enters its operational handover phase. Dave’s key to the electrical cupboard is confiscated. He is no longer permitted to touch the switch.

A week later he is invited to Light Bulb Production Readiness: Critical Path and Outstanding Delivery Actions.

“Dave, we’re a bit worried. The light hasn’t been turned on in production.”

“Correct.”

“What’s preventing that?”

“You took my key away.”

“Yes, but that was part of the agreed handover process.”

“Then ask your electrician to turn it on.”

“But can you confirm it will work?”

“I tested it in development and test. I haven’t been allowed into production.”

“Could you do that today?”

“No.”

“Why not?”

“Because. You. Took. My. Fucking. Key.”

The programme manager writes something in his notebook. “Right. So we’ll capture that as an outstanding action for Dave.”

Dave points out that the organisation now owns the installation, the cupboard, the switch, the keys and the electrician.

“Absolutely. But you’re still our subject matter expert. We’d really appreciate it if you could take ownership of getting this over the line.”

Dave asks whether that means he can have his key back. It does not.

Martin intervenes. “Perhaps it would help to separate the question of who has access to the switch from the question of who is responsible for ensuring the switch gets switched.”

Martin is delighted. He has identified two distinct workstreams.

6. Scope, security and the observation framework

To reduce risk, the organisation decides to deploy a single bulb. The rest of the building will stay dark while it considers the security implications of illuminating multiple rooms.

Somebody asks who is responsible for observing the room once the switch is flicked, and whether that person is authorised to confirm that illumination has occurred.

Martin raises a further concern. The room is currently lit by daylight. How will they distinguish successful illumination from a false positive?

The meeting agrees the bulb must be tested after sunset. Unfortunately, Electrical Operations does not provide out-of-hours support.

Then somebody asks whether the bulb has been penetration tested. Could light visible through the window constitute an information disclosure vulnerability?

The security team requires a representative production environment. The light cannot be turned on until the penetration test is complete. The penetration test cannot begin until the light is on.

The meeting concludes that there is a dependency. Everybody nods solemnly. It is added to the risk register.

Dave’s contract is extended for another month.

7. The electrician builds something else

Dave is no longer upset by any of this.

He is paid his full rate to attend meetings about a bulb he finished installing months ago. He has no access and no authority, and most questions can be answered by pointing at one of forty-two documents.

This leaves him with rather a lot of spare time.

So he builds an automated electrical installation system. Robotics, machine vision, software that designs a circuit, installs it, tests it, finds its own defects and fixes them. Before long it can wire an entire house without him.

Martin, meanwhile, is having an excellent year. He has identified seventeen documentation gaps, chaired eleven stakeholder meetings and escalated three critical dependencies. His performance review describes him as instrumental in driving the programme towards production readiness.

Not a single photon has emerged from the production bulb.

Martin is promoted to Head of Illumination Strategy.

Nobody asks whether he knows how to change a light bulb. That would be rather beneath him.

8. Governance is not delivery

I am not suggesting governance is pointless. The more serious the consequences of failure, the more important it is to establish that a system is safe.

But there is a difference between governance that reduces risk and governance that makes people feel less anxious. One produces evidence. The other produces meetings.

Some organisations have become extremely good at observing delivery without participating in it. They can produce a beautifully colour-coded spreadsheet showing the Light Bulb Programme is 94% complete. Ask what is physically stopping the light coming on, and they have no idea.

The incentives are the interesting part. The electrician’s measure of success is simple: does the fucking thing work? His job ends when it does.

Martin’s job can continue indefinitely, provided there is always something else to discuss before somebody turns it on. Every delay produces a dependency. Every dependency produces a meeting. Every meeting produces an action. Every action proves Martin is indispensable.

It is a magnificent little perpetual-motion machine. Unfortunately, it runs entirely on other people’s productivity.

It would be a terrible shame to discover that the only person in the organisation who understands the light bulb is the one person they have forbidden from touching it.

Although it would explain the spreadsheet.

9. How many electricians does it take?

Dave attends what he has been assured is the final production readiness meeting.

“We’ve made tremendous progress. Documentation, handover, ownership model. I think we’re almost ready.”

Dave looks at the light bulb. It is off.

He checks his phone. His system has just finished another project. Three houses wired. Two defects found and corrected. No human intervention.

“Dave, are you comfortable the light bulb is ready?”

“Yes.”

“So when will it be turned on?”

“When your electrician turns on the switch.”

“Is there anything you need from us?”

“Not a thing.”

“Fantastic. We’ll capture that as an action for Dave.”

Martin raises his hand.

“Sorry, just one final point. Could we get a simple diagram showing which direction the switch needs to move?”

Dave looks at Martin. Martin looks at Dave. The programme manager looks delighted.

“Really good point, Martin. Let’s get that documented.”

The meeting closes. Everybody thanks everybody else for their time.

Dave’s contract is extended for another month. He opens his calendar.

Light Bulb Production Readiness: Weekly Progress Meeting. Recurring. No end date.

He accepts. After all, the light bulb isn’t going to turn itself on.

Although, funnily enough, the one Dave has just designed probably will.

Relay was originally conceived as a synthetic company.

That was always the mental model.

It had a board of directors. It had HR vetting agents. It had different roles, delegations and responsibilities. In some ways it could behave more flexibly than a real company because the board didn’t have to sit at the top grilling a CEO about what was happening underneath it. It could drop straight into a department, interrogate what was happening there, challenge decisions and then move somewhere else.

I’ve spent an extraordinary amount of time thinking about the organisational structure of this thing.

Then this morning something embarrassingly obvious hit me.

I’ve forgotten the fucking PA.

I am effectively the CEO of this synthetic company and I am still scheduling my own day.

Why?

Why am I chasing some company in Dublin because they still haven’t sent the DDR RAM that actually powers Relay? One of the sticks failed, so its main machine is currently running at half power.

Why am I chasing the people who currently have my lovely Felt IA FRD time trial bike?

Why am I moving appointments around, remembering who needs chasing, checking whether things have arrived and working out what needs doing next?

This is ridiculous.

I need a PA.

So I went to Relay’s chief architect and basically spewed all of this at him.

I said: I need a PA. What would we need to build? What machinery are we missing? How would you approach it?

And I got perhaps the most satisfying answer I could have received.

Essentially:

Nothing much.

We already have the machinery.

We already have the UIs.

We already have the agent infrastructure.

We already have Eyes and Hands.

We already have connectors.

We already have Relay interrogating work, priorities, context and state.

This is just another role.

Give an agent access to the appropriate personal workload, calendar, messages and external systems. Let it interrogate what needs doing, chase things, reshuffle things, surface decisions and use Eyes and Hands where necessary.

That’s it.

There isn’t some enormous missing architectural component.

It is largely an implementation of things we have already built.

Probably a couple of hours’ work.

And oddly, that gave me more confidence in Relay than almost anything else this week.

Because that is what you want from an architecture.

You want to be able to walk up to it one morning and say:

Shit. We need one of these.

And for the answer not to be:

Right. We need another subsystem.

It should be:

Fine. That’s another implementation of the model we already have.

The early versions of Relay were full of things I had invented myself.

Increasingly, the doctrine is the opposite.

Find the established pattern. Find the project. Find the GitHub repository. Use the standard protocol. Put the thinnest possible skin over it. Don’t invent another bloody abstraction unless Relay genuinely needs one.

So discovering that I had somehow constructed an autonomous software company with a board, HR, engineering departments and external workers but forgotten to hire myself a PA was quite funny.

Discovering that adding one barely disturbs the architecture was much more interesting.

That feels like a good sign.

One of the interesting things about having a Substack and, by the way, we're now getting more than 10,000 article reads a month, which is pretty freaking amazing, so thank you is that you start to notice patterns in the comments.

The same characters keep coming back.

The same arguments. The same insults.

You're a eunuch.

You're a pervert.

You're mutilated.

You're not a woman.

Week after week. Article after article. They return to tell me again.

I had exactly the same thing when I was on X. The same people underneath everything I wrote. Following me around. Waiting for the next opportunity to explain, once again, how revolting or ridiculous transgender people apparently are.

And I've come to a conclusion about some of them.

I think they're fighting with themselves.

I think they're constructing an enormous internal scaffolding of arguments designed to suppress something they absolutely do not want to examine.

I think they're trying to convince themselves that whatever they're feeling, whatever curiosity or recognition keeps dragging them back to this subject, absolutely cannot mean anything about them.

And I think that because I did it.

For years.

I had an enormous history with gender stretching back through my life, and I still spent roughly a decade finding reasons why I couldn't possibly be transgender.

I rationalised. I dismissed. I argued. I built intellectual structures around myself.

Anything rather than open the bloody door.

And here's the clever bit.

If a man simply spent every day obsessively arguing about whether people like me should exist, it would start looking rather peculiar very quickly.

So you need somewhere to hide.

And transgender politics provides some absolutely magnificent hiding places.

Women's rights.

Bathrooms.

Sport.

Children.

Suddenly you're not a man spending hundreds of hours thinking about transgender people.

You're defending women.

You're protecting children.

You're preserving fairness in sport.

You're fighting misogyny.

Perfect.

Now the fixation has a noble purpose.

You can read every article. Watch every video. Study every surgery. Debate every hormone. Examine our bodies. Discuss our genitals. Follow transgender people around the internet and write thousands upon thousands of words about us.

And every time that tiny uncomfortable question appears. Why am I so interested in this? You've already built the answer.

Because you're protecting society.

I don't think that explains everybody who objects to transgender people. Obviously it doesn't.

But the ones who cannot leave it alone?

The ones who return week after week?

The ones who seem to know more about transgender medicine than most transgender people?

The ones who are somehow underneath every article, every photograph, every discussion, endlessly announcing how completely uninterested they are in becoming anything remotely like us?

Those people interest me.

Because I recognise the architecture.

I built it myself.

And eventually mine collapsed.

So, to all my angry male friends who like to spend their time commenting on my Substack:

Come on in, boys. The water's lovely.

Cross the line.

Accept yourself.

You might find you have rather less to be angry about.

The Colonel is not speaking to me. Until this week he was the famous one in this house, and he has taken the change in billing badly.

Because a few weeks ago I got an email from Monika Kowalska, asking if I’d give an interview for The Heroines of My Life. For those who don’t know it, it is quite the institution. Monika has been interviewing transgender women from all over the world for well over a decade. Hundreds of us. Writers, politicians, scientists, athletes, activists, and the archive reads like a who’s who of women who walked through the fire and came out the other side worth talking to. It’s the sort of site I used to read late at night, long before I’d done anything worth being asked about.

So yes, I feel like I’ve arrived. It was an honour to do.

Here is how Monika introduced me, which I’m including mostly because reading a stranger’s tidy two-paragraph summary of your own bonkers life is a genuinely out-of-body experience:

Stevie Bennett is a British transgender woman, writer, software architect, former quantitative trader, Ironman finisher and father of three. After spending decades suppressing her gender identity, she transitioned in middle age and has since documented her experiences through her writing and social media. Stevie built a long career in software development and architecture and also worked in quantitative trading. Before transitioning, she was married and became the parent of three children. She met her future wife in Dublin when she was thirty-six, and the family later lived in London and rural Ireland. Endurance sport became another important part of her life. After taking up cycling and triathlon, Stevie completed a full Ironman in 2016. Medical investigations into her hormone levels later became an unexpected turning point in her life. After discovering unusually low testosterone and experiencing subsequent hormonal and physical changes, including feminisation, she began confronting the transgender identity she had spent much of her life trying to suppress.

Her transition brought both profound personal fulfilment and significant upheaval. Her marriage ended, and she has written openly about the joy of finally living as herself, alongside the grief and loss connected with the changes to her family life. Stevie has since undergone gender-affirming surgery and continued to document her experiences through her publication, Fast Track Femme, where she writes about transition, family, divorce, surgery, ageing, dating, technology and artificial intelligence. Alongside her writing, she continues to work in technology and has explored the use of AI agents in software and creative projects. Today, at fifty-seven, Stevie is continuing to build a new life while remaining a parent, technology professional, endurance athlete and writer. Her story is an unusual combination of a decades-long hidden transgender identity, family life, elite endurance sport, an unexpected hormonal journey and a rapid public transition later in life.

I’m not going to reproduce the interview here. It’s Monika’s work and it belongs on her site, so go and read it there. But I’ll tell you it covers the lot: Ironman, Graves’ disease, three countries’ worth of surgery, a month of enforced silence, my mother, loneliness, white jeans at the worst possible moment, and what comes next.

If you’re interested, this is it:

link to the interview

And while you’re there, have a rummage through her archive. It’s quite something.

An aside: Okay, this is a big deal for me. This is the first time I’ve actually done this voiceover in my voice. We are still only at the two-month phase now, and so we haven’t really done a lot in terms of altering pitch, etc. It’s better than it was, but we’ve got a long way to go. Hopefully I’ll record with my voice over the next few months and it will sound better. We will see.

It’s Sunday morning in rainy Cork and I’m sitting in my office with Chester on my knee, his favourite place when I’m working.

Thank God he’s a chihuahua and not a Labrador.

I’m looking out of the window at the grass, which has now turned into a meadow after three weeks of neglect, and trying, for about the fourth time, to write an essay I’ve wanted to write for a very long time.

Over the last couple of years I’ve had a lot of conversations with trans women about mental health. I’ve never wanted to break anybody’s confidence, so the people in this essay are composites. Circumstances have been altered, timelines moved, details merged. The psychology is real. The biographies are not.

What has stopped me writing it before is that I’ve never quite known what the question was.

I think I do now.

Why do so many transgender people seem to struggle with their mental health?

Even writing that makes me uncomfortable because I know exactly what people hostile to us will do with it. Aha, they’ll say. There you are. You’re all mentally ill in the first place.

No.

It really isn’t that simple.

But I am equally unsatisfied with the opposite explanation, which is that the whole thing can essentially be filed under minority stress and we can all go home. Minority stress is real. Rejection is real. Discrimination is real. Fear is real. I have experienced enough of all of them to have no interest in pretending otherwise.

But I don’t think they explain everything.

So which came first?

The chicken or the egg?

Are some people already psychologically vulnerable before transition? Does dysphoria create that vulnerability? Does transition improve mental health while simultaneously putting it under enormous strain? Does the reaction of everyone around you do the damage? Does passing matter? Does money matter? Does age matter? Does social media make the whole world feel much more frightening than the one outside your front door?

Or have I simply met an unusually troubled bunch of transgender people and built a theory around a distorted sample?

That last possibility deserves taking very seriously.

My introduction to Transgenderland was hardly random.

Before I transitioned, I searched obsessively for examples of what was possible.

Not research in the proper sense. More like longing with Google.

I found trans women who represented something I wanted to believe could happen to me. Successful women. Beautiful women. Women who had transitioned late and somehow landed elegantly on the other side.

And, if I’m being completely truthful, I also performed a private feasibility study while scrolling.

I think I could look better than that.

I think I could look better than that.

I think I could look better than that.

Oh. Probably not her.

I think I could look better than that.

Awful? Maybe.

Human? Definitely.

I wanted to know what was possible.

Eventually I joined an online fitness community for trans women. The fitness was almost incidental. What I really needed was people. At that point almost everybody from my previous life had rejected me, so I entered eagerly.

And holy fuck.

My previous social world had been almost comically respectable. Bankers, architects, teachers, doctors, professionals. Nice houses. Sensible jobs. Dinner parties. Ocado.

Then suddenly I was surrounded by addiction, psychiatric crises, interpersonal chaos, paranoia, people falling in and out with one another, families in pieces. For a while I developed what I can only describe as an uncomfortable Queen Bee of Normality feeling.

Am I the only person here whose life isn’t permanently on fire?

But the obvious problem with that conclusion is that my previous world had been massively filtered. I just hadn’t noticed the filters: education, career, income, geography, marriage, professional networks, social class, temperament.

Transgenderland selects primarily on one thing.

Being transgender.

That is an incredibly broad filter.

And a support community filters again for people actively looking for support.

Perhaps I had walked into the psychological equivalent of A&E and concluded everybody in Britain had a broken leg.

Instagram gives you the opposite distortion. Look there and you can find an endless parade of gorgeous young trans women who appear to have their shit spectacularly together. Perfect hair, tiny waists, friends, holidays, crop tops, smiling into the camera. Happy as Larry.

But Instagram is no more representative than a support group. The algorithm does not preferentially serve you somebody lying under a duvet having a nervous breakdown.

So somewhere between the support group and the impossibly glossy reel, there must be something resembling reality.

And reality, from what I can see, is wildly varied.

I know a woman who remains deeply unhappy after transition. She has a close relationship with her child and, from where I stand, things in her life that I would once have given almost anything for.

One night she was particularly low and I said something like, “At least your child still talks to you.”

“Yes,” she said. “She’s asleep beside me.”

That stopped me.

I had not seen my own children for more than a year.

I was tentatively trying to rebuild those relationships from a distance, and here was somebody lying beside one of the things I missed most in the world and still unable to feel comforted by it.

That does not make her ungrateful.

It means we are psychologically different.

Her glass can be half full and she can somehow experience it as three-quarters empty.

I tend to do the opposite. Not always. I have had very bad periods. I have drunk too much at times. I have sat alone and wondered what the fuck I had done.

But eventually my engine restarts.

Work. Build something. Research something. Fix something. Make a plan. Move.

I love working. Give me something interesting and I become a small overcaffeinated dynamo. Perhaps that is healthy. Perhaps sometimes it is avoidance.

Probably both.

I have also known women whose addictions or other serious psychological problems predated transition by years. When things start to fall apart again, I have sometimes found myself saying some version of: get rid of what you have, call somebody qualified, and do it now.

Friendship has limits.

Sometimes the most useful thing you can do is recognise when you have reached yours.

And this is where the simple causal story breaks down. If somebody has a long history of trauma, addiction or psychiatric instability, it becomes intellectually ludicrous to meet her after transition and say: see, transgender people are mentally unstable.

There is an entire human biography sitting there.

Transition is part of it.

It is not all of it.

Then there are women whose transition itself goes reasonably well while the surrounding architecture of their lives begins to collapse. Marriage. Family. Home. Identity.

They sometimes frame the pain as people being unable to accept the real them.

And I keep wanting to say something less comforting.

Your partner can love you and still not be attracted to the woman you have become. Your children can love you and still struggle. Your transition can be right and still hurt other people.

Those things are not mutually exclusive.

Transition can be absolutely right and still create casualties.

And then there’s Sarah.

Sarah has a sensible job in procurement, a nice enough house, a cat and a garden she remembers to mow more often than I do. Her Instagram is full of material so catastrophically uneventful that I find it strangely soothing. A while ago she posted a short video of herself making lasagne.

Two hundred and eleven likes.

I adore Sarah.

Nothing is on fire.

She goes to work. She comes home. She potters. She meets friends. She does normal things and, as far as I can tell, being transgender is simply one fact about her rather than the organising principle of her entire existence.

Which raises the question I keep coming back to.

What separates one outcome from another?

And, more awkwardly, what separates me?

Because externally my transition was a fucking explosion.

My marriage ended. My relationship with my children collapsed. Friendships disappeared. Almost my entire previous social architecture went with it.

If the theory is simply that rejection destroys the mental health of trans people, I should be in pieces.

And yet my mental health improved.

Dramatically.

Before transition I was an angry man. Not permanently. Not cartoonishly. But increasingly angry.

Political obsession. Bitcoin libertarianism. Ayn Rand. Stupid ideological battles. Constantly projecting outward. Solve the world. Fix the world. Argue with the world.

Angry, angry, angry.

Looking back, I don’t particularly like him.

I sometimes wonder how my wife tolerated him.

Then I transitioned and enormous amounts of that simply evaporated.

That is the paradox at the centre of this essay.

Internally, transition made me healthier.

Externally, it blew my life to pieces.

The thing that improved my mental health was also the thing that created the circumstances in which I needed every ounce of mental health I had.

And that is why I distrust the idea that transition simply “makes you happy”.

Sometimes people approach it with the same magical logic as the miserable couple who decide to have a baby to bring them closer together.

You think: Oh Christ.

A baby may be wonderful. It may also introduce sleep deprivation, money worries, arguments, fear, responsibility and an astonishing quantity of shit.

Transition can be similar.

It can fix something absolutely fundamental without fixing everything else. It does not cure loneliness, addiction or trauma. It does not change your personality. It does not make your spouse gay. It does not manufacture friends.

It may solve the thing that made it necessary and introduce five completely new problems before lunchtime.

I knew this intellectually before I transitioned. I deliberately guarded against the utopian idea that once I became a woman everything would become marvellous.

This was not a ticket to Disneyland.

It was something I needed to do.

Then I would still have to live.

I think that matters.

Call it self-awareness, metacognition, expectation calibration, whatever you like. Some people seem better able to watch themselves thinking, to notice catastrophising, to distinguish “this is awful” from “everything is awful”.

That ability probably existed before transition.

And increasingly I wonder whether transition, rather than creating an entirely new psychology, often amplifies the psychological equipment you bring with you.

Not inevitably. Not in everyone. But transition places extraordinary pressure on identity, uncertainty, relationships, embodiment, grief and hope. Under that sort of pressure, the ways you already deal with the world suddenly matter enormously.

If you catastrophise, there is plenty to catastrophise about. If you need certainty, transition offers remarkably little. If you externalise every setback, there will be no shortage of people to blame. If you cope through work, humour, planning or sheer bloody-mindedness, those traits suddenly become extremely useful.

Transition may not create those tendencies.

It may simply turn the volume up.

Which brings me to late transition.

Late transitioners often enter this like excited puppies.

I did.

My God, the hope. The possibility. The clothes. The body. The idea that after forty or fifty years you might finally get to do this.

But there is something I would say to the person standing outside looking in.

You have no fucking idea how bad it can get.

I mean that seriously.

Not because transition is wrong.

Because by middle age you have built an enormous structure around yourself: marriage, children, career, money, friends, decades of shared history.

And suddenly every relationship in that structure has to renegotiate itself.

A twenty-two-year-old may have plenty to lose. But usually not forty years of accumulated architecture.

Do not mistake knowing that you need to transition for knowing what transition is going to do to your life.

Those are completely different forms of knowledge.

Then there is the question nobody particularly likes discussing.

Passing.

I suspect it matters enormously, although I think “passing” may be the wrong word.

The thing that matters psychologically is probably social friction: being stared at, being misgendered, seeing somebody hesitate, wondering whether you have been clocked, bathrooms, dating, talking on the phone.

I cannot know whether I pass completely.

Nobody can.

Unless you crack somebody’s skull open, you cannot know what they have inferred.

I can only observe how I am treated.

And these days I am treated normally.

Maybe people know.

Maybe they don’t.

I have no idea.

Would I have coped as well if my transition had not physically worked out as well as it has?

Probably not.

That sounds shallow.

But I’m not sure it is.

The entire endeavour is partly about embodiment.

My mother told me recently that I looked really pretty.

I welled up.

That mattered.

Appearance also carries extra freight during transition because it is doing several jobs at once: attractiveness, femininity, safety, belonging, and whether the whole bloody thing feels as though it is working.

That is a lot to hang on a mirror.

Then there is uncertainty.

Transition is an extraordinary exercise in surrendering control. You do not know exactly what hormones will do. You do not know what surgery will do. You do not know who will stay. You do not know how your children will react. You do not know whether dating will become easier or impossible.

At one point, before my first major surgery, I stood naked in Istanbul in front of a surgeon and several members of staff while they drew lines all over me and discussed my body in Turkish.

Breasts out. Loose skin. Penis. Everything.

Hmm.

What shall we do with this one?

There is no elegant Instagram caption for that.

Transition contains indignity, fear, disappointment and uncertainty alongside all the joy.

You need to be able to tolerate some of it.

And I am not sure our communities are always very good at saying that.

I understand why.

Trans people are attacked relentlessly. When anything nuanced can be dragged out of context by somebody who thinks your existence is evidence of social collapse, nuance starts to feel dangerous.

So slogans emerge.

It isn’t a choice. Be yourself. Live authentically. Everything will be better.

Some contain important truths.

But slogans are poor preparation for enormous life events.

“Be yourself” is emotionally lovely.

It is not a risk model.

And if somebody is about to reorganise almost every important relationship in their life, perhaps we owe them more than encouragement.

I also think the internet can make all of this worse.

Some trans people I know live in a state of almost permanent political alarm. The threats they worry about may be real. I am not qualified to tell them otherwise.

But I sometimes want to ask a much smaller question.

What actually happened to you today?

Not online.

Today.

You got up. You ate breakfast. You went to work. You came home. You fed the dog. You went shopping. Perhaps someone looked at you. Perhaps nothing happened at all.

Online reality and lived reality are not always the same thing.

Spend enough hours consuming material telling you that the world hates you and eventually your nervous system may start behaving as though the mob is permanently outside your front door.

Again, perhaps I find that easier to say because I move through the world with relatively little social friction.

That caveat matters.

So where does this leave the chicken and the egg?

With something messier.

I don’t think there is one causal arrow.

Some people arrive at transition carrying serious psychological problems. Some have been damaged by years of dysphoria. Some experience transition as an enormous release and then discover that the release came with divorce, loneliness or financial stress. Some are treated badly by the outside world. Some encounter almost no hostility at all.

And underneath all of that sits the person who arrived at the starting line.

Their temperament.

Their history.

Their habits of thought.

Their coping mechanisms.

Their ability to live with uncertainty.

Their capacity to recover.

That is why I keep coming back to amplification.

Not as a law.

As the closest thing I have found to an explanation for why the outcomes can look so radically different.

Transition puts enormous force through a human life.

What happens next depends partly on where that force lands.

I have spent a lot of time wondering what clinicians are supposed to do with any of this.

I don’t know.

Genuinely.

My own path tells me almost nothing about conventional gatekeeping because money and determination allowed me to route around most of it. I decided I was doing this, and then I did it.

Every neat rule I invent immediately produces somebody for whom that rule would be disastrously wrong.

So I am not going to pretend I have solved clinical practice over breakfast.

What I can say is what I would tell the woman standing where I stood a couple of years ago.

The one staring at photographs.

The one imagining hormones.

The one wondering what she might look like.

The one thinking that perhaps, finally, she can live.

I would not tell her not to do it.

God, no.

I would tell her that she has absolutely no idea what is coming.

That she may become happier than she has ever been and lose things she cannot imagine losing.

That those two things can happen at exactly the same time.

For me, transition made me psychologically healthier and made my life objectively harder.

Both happened at once.

That contradiction is not a flaw in the argument.

I think it may be the argument.

For me, it was better on the other side.

Much better.

But better and easier turned out to be completely different words.

I know, I know. Another Wittering article.

But this one is very, very short. It isn’t really a post and it's too long for a Note, so by process of elimination it must be a wittering.

Today was a funny old day.

I mentioned in my previous post that I was interviewed recently for a blog. This afternoon, for no particularly good reason, I looked up who else from Ireland had been interviewed and spotted the name of another transgender woman. Cork, too. Even more strangely, when I looked her up on LinkedIn, we were already first-degree connections. We’d apparently connected about six years ago.

So I sent what I thought was an entirely friendly little message along the lines of:

Hello! Small world. Look at this, we’re already connected from back in the days when I was the other fella.

I may as well have written:

Can I come round to your house and shit in your mouth? Also, I’m a right-wing fascist.

Jesus Christ.

She went off at me. Not mildly irritated. Not slightly frosty. Force Ten. Paragraph after paragraph about inappropriate language, flippancy, over-familiarity, gender dysphoria, trans activism and why on earth had I contacted her in the first place.

I sat looking at the screen thinking: What the fuck just happened?

Because I was talking about myself.

I was the other fella. Or, if you would prefer the official long-form version: six years ago I was still living socially as a man, presenting as male, using a male name and looking considerably less like the woman currently occupying my LinkedIn photograph.

“The other fella” seemed quicker.

It struck me afterwards that if your peace of mind requires everybody around you to use exactly the right language, all the time, according to a very particular interpretation of what that language means, life is going to be extremely hard work.

And in this particular case there was another slightly surreal element to it.

I am quite obviously transgender.

Quite spectacularly so, really.

I write endlessly about transition. I have spent an amount of money on transition that would have bought an extremely respectable Ferrari. I am probably not the first person you’d nominate for the local anti-trans society.

So if even I can accidentally fail the terminology exam while making a joke about my own bloody life, I think we may have made the exam slightly too difficult.

Anyway, I wandered off to Reddit afterwards in a mild huff and looked at the comments on something I’d posted earlier.

And there it was.

A phrase that produces roughly the same physical response in me as Sideshow Bob stepping on a rake.

“When my egg cracked…”

Hnnnnnnng.

I really dislike that phrase.

And I’ve been trying to work out why, because obviously I know exactly what it means. It means the point at which somebody finally realised, accepted or admitted to themselves that they were transgender.

Perfectly reasonable concept.

Still hate the phrase.

I think there are three reasons.

The first is that “my egg cracked” makes an enormously complicated thing sound like a single cute event.

Monday: egg.

Tuesday: crack.

Wednesday: woman.

That isn’t remotely how I understand my own life. There were clues. There were denials. There were periods when I knew things and then somehow managed not to know them again. There were bargains with myself, compromises, stupid decisions, sensible decisions and eventually a point where continuing as I was became impossible.

There wasn’t an egg.

There certainly wasn’t a satisfying little crack.

The second reason is that I find it slightly infantilising. It has the vocabulary of something adorable happening to a baby bird.

My transition has contained many things.

Adorable poultry has not been prominent among them.

And the third and I think this is the big one, is that I don’t like in-group language very much.

Not just this phrase.

Egg.

Egg cracked.

Top surgery.

Bottom surgery.

Baby trans.

There are loads of them.

And before somebody gets cross with me, I am not saying anybody else shouldn’t use them. If “my egg cracked” describes your experience perfectly, crack away. Have an omelette. I genuinely do not care.

What I dislike is the faint sense that once you belong to a particular category of person, you are supposed to inherit its vocabulary as well.

I don’t want to.

I don’t want transition to come with a phrasebook.

I had a vaginoplasty. That’s what the operation was called. “Bottom surgery” always makes me feel faintly as though I’ve been to a garage and had some work done underneath.

And perhaps this is why today’s two completely unrelated encounters ended up joining together in my head.

At one end, somebody was furious because I wasn’t precise enough about my own transition.

At the other, I was irritated by a community vocabulary that sometimes feels too prescribed.

Maybe I’m just awkward.

Actually, scratch the maybe.

But I do think there is something worth defending here: the right to describe your own life in your own language.

I was the other fella.

Somebody else’s egg cracked.

I had a vaginoplasty.

Someone else had bottom surgery.

We all know roughly what everybody means.

Perhaps we could occasionally grant each other that much.

Well, well, well.

Apparently I am now established.

A few days ago I did an interview for Heroines of My Life, Monica’s transgender blog, which has been running for about ten years. There are hundreds of transgender women on there. I searched for a few women I remembered from years ago, women whose transitions had inspired me when I was still standing on the other side wondering whether any of this was actually possible.

There they were.

And from 15 September, apparently, there I will be too.

So. I’ve arrived.

Sort of.

This isn’t actually an article about that, although if Monica lets me, I’ll publish the interview here too.

This is the article I’ve been trying to write for nearly a year and have made a complete arse of about four times.

At one point, while recovering from bottom surgery, I tried to write about why I had gone to Thailand and how I had chosen surgeons. Then I started another article about how to assess different surgical options. Then, even worse, about nine months ago I started writing an incredibly arrogant article about how to transition successfully.

Dear God.

I had theories. I had frameworks. I had sections about embodied femininity. I had more frameworks. I had basically decided that, having transitioned for about five minutes, I had somehow reverse-engineered the entire subject.

I found it recently.

Slightly embarrassing.

So let me be clearer about what this one is.

This is a guide to what I did for my transition.

That’s it.

It is not a guide to what you should do. I’m not saying this was the optimal transition, or the safest, or the cheapest, or the most sensible, or the most emotionally enlightened.

It is simply the sequence of things I did, why I did them, what I was thinking at the time, and what I think about those decisions now.

That distinction matters to me because my thinking has changed.

I used to have this blueprint idea in my head: this is how you do it efficiently, this is the correct order, why on earth wouldn’t everybody do roughly what I did?

I don’t think that anymore.

People have different bodies, faces, finances, families, health, appetites for risk, dysphoria, ambitions and definitions of what a successful transition even means.

So this is mine.

Besides, I’ve learned something else over the last couple of years. Transgender people occasionally ask me for advice, I give it, and then they bloody ignore me anyway.

Probably for the best.

I ran it like a military operation

I have said before that I treated my transition like a military operation.

That sounds more dramatic than it was, but fundamentally it is true.

I had a fairly definite aesthetic idea in my head of where I wanted to end up, and I worked backwards from it.

I used a piece of software called Kanban Flow.

Every week I would rearrange the priorities.

What is number one?

What is number two?

What is number three?

What actual things am I doing this week?

At the beginning, the objectives were enormous.

Lose weight.

Sort out my skin.

Deal with facial hair.

Sort out my body.

Sort out my face.

Sort out my voice.

There was always something sitting at the top of the board demanding attention.

I still use the same system now.

The funny thing is that the board has gradually become much more boring.

Voice rehabilitation.

Finish facial electrolysis.

Skin treatments.

Possibly RibXcar.

General maintenance.

I think that is probably progress.

At the beginning, though, I had a visual target.

There were five or six transgender women around my age whose transitions had made a huge impression on me. Most of them have disappeared from public view now and I won’t name them. One who is still very public is Victoria Perera.

What struck me about these women was not simply that they had had good surgery.

They looked like women.

More than that, they seemed to understand how to look like women.

That was what I wanted.

Good face. Good skin. Good brows. Good makeup. Good clothes. Good mannerisms. Good surgery.

Not young. Not some Instagram fantasy of being 23 again.

I was in my fifties.

I wanted to look like an attractive, elegant middle-aged woman.

And I’m not going to pretend attractiveness didn’t matter.

It mattered enormously.

Passing mattered too, obviously, but I did not want merely to cross some technical gender threshold while hating what I saw in the mirror.

I wanted to look good.

That was always part of it.

The thing I hid underneath all the planning

Looking back at the organisation, the dates and the way I moved from one thing to the next, I probably look far more confident than I actually was.

I wasn’t confident at all.

I was terrified.

I have videos from early transition where I used my webcam almost like a confessional diary. I look back at some of them now and find them heartbreaking.

There is one from February 2025 that I have watched perhaps a hundred times.

I am sitting in my office and I say something like this:

In two years’ time, I want to be walking down Oliver Plunkett Street in Cork, with my earrings on, wearing a nice coat, heading back to my Range Rover Evoque.

Someone will look at me and say to her friend:

“Is that woman transgender?”

And the friend will say:

“Yes. I think so. I’m not sure. But she looks all right, doesn’t she?”

And I say:

That’s my dream.

Then I joke that what will probably really happen is people will look at me and think I look ridiculous.

That was where my expectations genuinely were.

Not stealth.

Not perfection.

Not some fantasy where nobody would ever know.

I hoped I might look like a reasonably attractive trans woman who made people hesitate for a moment.

I was scared I was about to throw my entire life away and end up looking awful.

And despite all the planning, I don’t think I properly started believing this could work until June or July 2025.

There is another video from around July where I am sitting in my office cutting between footage of myself then and an old video of myself as a man.

I am laughing.

Actually giggling.

“I cannot believe how much I’ve changed.”

I think that was the point where my internal narrative shifted from:

God, I hope this works.

to:

I think we can do this.

January 2025: the nuclear option

Before the major surgeries, there was skin.

My skin was pretty poor around my face.

I had acne pitting around my chin, old shaving damage, texture problems and generally forty years’ worth of evidence that somebody had been dragging a razor around my face.

I had already been having Botox and fillers for a few months, and my cosmetic doctor told me that the nuclear option for the skin was fully ablative CO₂ laser.

I had it done on 11 January 2025.

I would love to show you the pictures.

I am not going to.

I looked like an actual monster.

Not slightly pink.

Not a bit swollen.

A monster.

For about a week I hid in the house.

When I had to do the school run I put on sunglasses and a woolly hat and tried to move through society without frightening children.

It was brutal.

It also made a massive difference.

A few months later I started doing Sculptra and eventually had roughly four or five sessions.

In February I started Botox into my masseter muscles to reduce the bulk of the jaw muscles. I had it done again around July.

I remember turning up at my cosmetic doctor armed with an enormous amount of ChatGPT-assisted research into transgender Botox techniques.

She looked at me as if she had accidentally booked an escaped medical researcher.

I have also had filler in the medial cheek to soften some remaining hollowness, a couple of millilitres in my lips because nature had given me practically none, and the usual Botox every few months.

In February 2026 I did another round of CO₂ laser, mainly on my chin.

That one disappointed me.

The first treatment made a huge difference.

The second one seemed to do remarkably little.

My chin is still one of the things I am not entirely happy with.

Which may already tell you something about the nature of all this.

The goalposts do move.

The face was the big one

Nothing mattered to me as much as my face.

Nothing.

Not bottom surgery.

Not breasts.

Not my voice.

The face was easily the most important thing.

I had spent months playing with AI and trying to create realistic approximations of what I might look like after surgery. I studied other women. I studied foreheads, jaws, chins and noses until I could probably have sat an exam in facial geometry.

The strange thing is that, initially, I deliberately chose not to make FFS my first major operation.

There was a period early on when I still genuinely believed I could save my marriage.

So I started by speaking to ordinary cosmetic surgeons about a facelift, neck lift and rhinoplasty.

My idea was that I could do those first, sit with the result for perhaps a year, try not to make things any more difficult at home, and then maybe come back later for the forehead, chin, jaw and bone work.

In March 2025 I went to see Facial Team in Spain and explained this.

I effectively told them:

“I know this is completely arse-about-tit surgically, but I have personal reasons.”

They thought it was arse-about-tit too.

They were right.

I was trying to organise surgery around preserving something in my personal life.

By May, I knew my marriage was over.

And once I accepted that, my entire strategy changed.

The question stopped being:

How do I make this easier for everybody around me?

and became:

If I am doing this, what actually gives me the best chance of the result I want?

Facial Team remained my likely choice for perhaps another couple of months.

There were things I liked about them.

But I became increasingly uneasy about the aesthetic direction.

I went through their website looking particularly at older women.

I kept seeing phrases like:

“natural result”

“subtle”

“not overdone”

And during consultation I repeatedly heard versions of:

“You need to be realistic about what can be achieved at your age.”

Now, they did not literally say:

“Be realistic, love, you’re an old bag.”

But that was increasingly how it felt to me.

And my brief was quite specific.

I said:

I want to look like a woman over 50 who has had a bit of work done.

I didn’t particularly care if somebody could tell I’d had cosmetic surgery.

I cared whether it was good cosmetic surgery.

Those are not the same thing.

How do you choose a surgeon?

This became one of the harder questions.

Initially, I put enormous weight on before-and-after photographs.

Then I started thinking about what those photographs actually mean.

Imagine a surgeon performs a thousand FFS procedures.

There will almost certainly be five spectacular results.

Those five will be on the website.

What I actually wanted to know was:

What does the median result look like?

And, even more specifically:

What happens to someone my age, with my starting face, my skin, my bone structure and my particular problems?

That is almost impossible to know.

The ideal experiment would be to take a hundred sets of identical transgender twins, send them to different surgeons and compare the results.

Sadly, this research design appears to have some ethical shortcomings.

So over time I relied on two things:

before-and-after photographs, and personal recommendation.

Photographs told me whether a surgeon was capable of producing an aesthetic I liked.

Recommendation gradually became more important.

Several of the women whose results had originally made me believe transition could work at my age had been treated by Jordan Deschamps-Braly.

Eventually I thought:

Why am I gravitating towards Spain because it is convenient when the results I actually admire seem to be coming out of San Francisco?

June 2025: Turkey first

Before I got to San Francisco, however, an opportunity opened up to deal with my body.

Years earlier I had gained a lot of weight and later lost it. I was left with poor skin around my abdomen that was never going to disappear through diet or exercise.

So the core procedure was a tummy tuck.

My theory at this stage was very simple:

If I am going under general anaesthetic, I want to get as much useful work done as reasonably possible.

So I added lipo 360.

And a Brazilian butt lift.

Because who doesn’t want one of those?

I was also very tempted to have breast implants done at the same time.

Right until the last few days, I was considering it.

Again, I held back because of family circumstances. I thought coming home having visibly altered absolutely everything at once was perhaps a little much.

With hindsight, I probably would have done the breasts in that operation too.

The surgery was scheduled for 6 June 2025.

I went in, stripped off, stood naked while the surgeon and his assistant drew circles and arrows over me showing where they were going to remove fat, cut skin and inject fat.

They kept pointing at different bits of me and saying:

“Not much fat.”

“Not much fat.”

“Not much fat.”

Probably the nicest insult I have ever received.

Then I went into theatre.

I was strapped down.

Anaesthetic.

And then I woke up.

Nothing hurt.

Nothing had happened.

There was a cardiologist there. The anaesthetist. Other people. Somebody translating.

They told me they had aborted the operation because my heart rate had dropped badly under the anaesthetic.

After they left, I burst into tears.

My first thought was:

That’s it. I’ve half-transitioned myself and now I’m stuck.

I thought maybe I simply could not tolerate general anaesthesia.

And within minutes I started bargaining with myself.

It’s all right.

I don’t look that bad.

I can live with this.

It could be worse.

There was an added reason I was terrified.

I had previously had Graves’ disease. My heart had misbehaved in the past and had gone into AFib a couple of times. I had failed an ECG before.

So cardiac testing scared the living daylights out of me.

They put me on a 24-hour ECG.

Then they put me on a treadmill with another ECG connected and gradually increased the speed.

I was pretty fit at the time.

They turned it up.

I said:

“Higher.”

They turned it up again.

“Higher.”

Eventually they stopped.

“That’ll do.”

“I could have gone much higher than that.”

Apparently even terror does not entirely suppress my competitive instincts.

The cardiologist eventually came back and told me my heart was healthy.

The problem was how my heart rate had responded to that particular anaesthetic approach.

They could alter the protocol.

All systems go.

The relief was enormous.

On 7 June, they performed the surgery.

When I woke up properly after the tummy tuck, I discovered something else.

Pain.

Christ alive.

It felt like somebody had shot me through the stomach.

I remember basically shouting:

“Morphine. Morphine.”

Somebody came along, gave me some, and the modern pharmaceutical industry restored order remarkably quickly.

The first three days were fairly rough.

Then it improved much faster than I expected.

About two weeks after I came home, I put on something I called my benchmark dress.

It was a fake pleather bodycon dress.

Not something I intended to wander around Cork wearing.

It existed almost as a measuring device.

I still had post-operative leggings on underneath.

I put it on, stood in front of the mirror and took a photograph.

And I remember thinking:

Holy fuck. I look like a woman.

That was the moment.

Not “my waist looks better”.

Not “this surgery has worked”.

It was the first time I looked at the complete silhouette and thought:

That is unmistakably female.

The hotel in Turkey was almost worth an article of its own.

It was included in the surgical package and seemed to be populated almost entirely by men recovering from hair transplants and women recovering from mummy makeovers.

We all shuffled around with drains hanging out of us, nodding politely at each other.

A sort of international cosmetic-surgery veterans’ association.

The whole operation was under €10,000.

For that particular group of body procedures, Turkey made sense to me because it was a huge, high-volume cosmetic-surgery market and this kind of work was routine there.

2 August: San Francisco

On 2 August I flew to San Francisco to consult Jordan Deschamps-Braly.

I stayed at the Taj Hotel beside his office.

The barman and I got talking.

“He comes in here.”

“What do you mean?”

“His name is on the bar.”

I walked over.

There was a bloody plaque with Jordan Deschamps-Braly’s name on it.

Then one day, while I was sitting there, he walked in.

The barman gave me a little wink.

So I went over.

Jordan looked at me.

“Who the hell are you?”

“I’m tomorrow’s patient. I’ll see you then.”

He was lovely.

I liked him enormously.

He had some connection with Manchester and knew an alarming number of English and Northern English expressions, which was quite funny coming from a Californian surgeon.

I was impressed.

I paid my deposit.

I was ready to proceed.

Then Thailand appeared.

Someone whose opinion I trusted in transgender medicine said to me:

“He is very good. But I don’t send my patients to him. I send them to this surgeon in Thailand.”

That threw everything up in the air.

I did not have the same volume of before-and-after photographs.

It was not about cost.

I trusted the recommendation.

There was another factor.

Other surgeons had told me the facelift and neck lift would need to be separated from the skeletal FFS work.

The surgeon in Thailand was prepared to combine them.

He was also prepared to do my breast augmentation at the same time.

For someone trying to compress the surgical phase into as few anaesthetics and recoveries as possible, that mattered.

So, at the last minute, I changed course.

7 and 8 September: seventeen hours

I flew to Thailand on 7 September.

The operation was too large to perform in a single day.

It became roughly 17 hours of surgery across two consecutive days.

Day one:

• breast augmentation

• lip lift

• tracheal shave

• open rhinoplasty

The nose was a major reconstruction.

They harvested rib cartilage, opened the whole thing and rebuilt it.

Then I woke up knowing that the following morning I was going back under.

And day two was the bigger one.

• Type III forehead reconstruction

• titanium plate

• facial fat grafting

• genioplasty

• jaw work

• deep-plane facelift

• neck lift

I have scars running behind my ears, around them, across my forehead and down the other side.

If you joined everything together at the back, you could probably peel the skin off my entire head.

That recovery was the hardest of the lot.

Not vaginoplasty.

FFS.

Simply because of the sheer volume of surgery.

I needed ice packs constantly.

I was swollen, bruised and absolutely battered.

But psychologically I dealt with surgery surprisingly well.

I approached it in much the same way I used to approach triathlon or endurance sport.

This part is going to be horrible.

Fine.

It ends.

Get through it.

By the time I reached voice surgery months later, the whole theatre ritual had become almost familiar.

Here we go.

Anaesthetist.

Hello boys.

Surgeon.

Nice to meet you.

Let’s do this thing.

Seeing my face

I stayed in Thailand for a month after the facial surgery.

For much of that time I looked as though I had been attacked by agricultural machinery.

But even very early on, there were glimpses.

There is a photograph of me in a bikini only seven or eight days after surgery.

I was still bruised and swollen.

And even then I remember looking at it and thinking:

Jesus Christ.

I look like a woman.

Then, towards the end of my stay, the clinic offered to take me to a makeup artist.

The idea was to disguise the remaining bruising and let me see the face underneath properly.

I cannot imagine many clinics in the West offering that.

Obviously I said yes.

She did the makeup.

I looked in the mirror.

And for the first time I could really see it.

The strange thing is that psychologically I accepted the new face almost immediately.

Within a couple of weeks it simply felt like mine.

The physical settling took vastly longer.

The forehead came in relatively quickly.

The chin took months.

The skin around the jaw and neck kept changing.

And the nose took the longest of all.

The tip gradually lifted and refined itself over months.

I used to look at it and think:

I’m not sure.

Now I actually quite like it.

If I compare photographs from one month after surgery with photographs now, the difference is enormous.

At the time I thought the one-month result looked wonderful.

Now I look back and think:

Oh dear.

I had a chin like Bo’ Selecta.

That is one of the stranger things about facial surgery.

A couple of millimetres here or there make an enormous visual difference.

At one month I now see swelling.

At one year I see my face.

And the part I love most surprised me.

My eyes.

I never particularly thought:

I hope I end up with lovely eyes.

But they are my favourite thing now.

I think they look natural.

I think they look feminine.

I like them.

I never expected that.

There are still things I would change.

I wish my nose were slightly smaller.

The surgeon explained that he could potentially have reduced it further, but that he was concerned about function.

I would rather be able to breathe, thank you.

I wish my chin were fractionally smaller.

I wish the facelift had been slightly tighter.

But these are now refinements, not catastrophes.

11 January: while you’re in there…

Four months later, on 11 January 2026, I went back to Thailand for vaginoplasty.

I have already written quite a lot about that:

So I am not going to reproduce the entire story here.

But I did continue my slightly deranged habit of asking:

If I am already under anaesthetic, is there anything else useful we can do?

My mid-face was still slightly hollow after the original fat grafting.

Jordan Deschamps-Braly had actually told me that facial fat grafting often required more than one round because not all of it survives.

So, while I was having vaginoplasty, I added cheek implants.

And some upper-back liposuction.

Because apparently I am incapable of booking a single-purpose anaesthetic.

I also asked about a leg lift.

The surgeon said no.

There are limits.

A leg lift and vaginoplasty put too much surgical tension and too many wounds in the same area.

So that one stayed off the list.

The vaginoplasty recovery itself was surprisingly manageable.

I had an epidural, which helped enormously.

What I did notice by then was the cumulative effect of all this surgery.

I had compressed a huge amount of physical trauma into a short period.

My exercise routine repeatedly disappeared because every time I started to recover and train properly again, another operation arrived.

I seemed to get ill more easily.

I had colds and flu more often.

I developed some horrible nerve and shoulder pain after vaginoplasty and had a few episodes of back trouble. I suspect some of that may have been connected to long periods immobilised on operating tables, although that is only my theory.

There was a physical cost to doing everything quickly.

Would I therefore conclude that I should have slowed down?

No.

That may be the lesson some people expect me to have learned, but it isn’t mine.

For me, getting through the major surgical phase quickly was still the right decision.

Makeup: the Laura Ashley years

One thing I underestimated massively was how much work goes into presenting yourself the way you want to.

Skin.

Brows.

Makeup.

Clothes.

Exercise.

Treatments.

Maintenance.

It is like painting the Forth Bridge.

You finish one end and immediately discover the other end needs doing again.

When I first started experimenting privately with makeup, I bought some cheap products online and vaguely remembered how I used to do makeup in the 1990s.

I looked like a model from a Laura Ashley catalogue.

I wasn’t completely clueless.

I had worn makeup before.

But modern makeup?

Correct foundation shades?

Not looking dated?

Not looking ridiculous?

I had work to do.

So I watched tutorials.

I experimented.

By April 2025 I would say my makeup was still a bit shit.

By July it was getting better.

Around November I booked a proper lesson.

I was supposed to be there for an hour.

I stayed for nearly three.

I offered to pay extra and she said it had been a pleasure.

She did say I already knew more than she expected, which was nice, but more importantly she taught me a lot.

Then a friend recommended another makeup artist, so I booked her too.

Again, I learned more.

That is basically how the whole thing worked.

Try something.

Get it wrong.

Improve it.

Repeat.

These days I can put on liquid eyeliner without making a complete arse of it.

I regard this as progress.

My two-mode eyebrows

My eyebrows were hilarious.

Even before I was fully out, while I was still sometimes presenting as male, they were already becoming suspiciously well shaped.

I had two eyebrow pencils.

One for female presentation.

One for male presentation.

If I was going out as myself, I would emphasise the arch.

If I was going out in male mode, I would literally colour the arch back in to make the eyebrow look less shaped.

A kind of eyebrow witness-protection programme.

The funny thing is that almost nobody noticed.

My wife occasionally did.

She would look at me and say something like:

“Jesus Christ, the state of your eyebrows.”

But somehow I mostly got away with it.

Three wardrobes

Clothes also went through phases.

I effectively have three generations of wardrobe.

The first is the pre-coming-out stuff, much of which I don’t particularly like anymore.

Then came the emergency wardrobe.

I suddenly needed enough women’s clothes to actually function, so we hit Shein hard.

Cheap dresses.

Cheap tops.

Experiments.

Some worked.

Some very much did not.

Then, gradually, my actual style developed.

I think that is inevitable.

You buy too much.

You try things.

You discover that something you loved six months earlier now makes you wonder what on earth you were thinking.

Eventually it starts to sort itself out.

I generally knew the direction I wanted to go in from the start.

Not theatrical femininity.

Not costume.

Just an attractive, fairly elegant woman in her fifties.

One problem disappears, another becomes louder

One thing I noticed repeatedly during transition was that whatever bothered me most would dominate everything.

Then I would deal with it.

And almost immediately something else would move to the top of the list.

Initially, the face was everything.

Nothing else came close.

Then the face was done.

And suddenly my attention moved elsewhere.

I would look at myself without clothes and think:

Christ.

This configuration now looks a little bit like a porn star.

There are trans women who are completely comfortable with that.

Fine.

I wasn’t.

So bottom surgery moved up the list.

Then bottom surgery was done.

And what was left?

The voice.

I don’t think the goalposts ever completely stop moving.

What changes is the urgency.

Earlier things felt like:

I need to fix this.

Now something like RibXcar feels like:

That would be nice.

Quite a difference.

The voice

Originally, I genuinely hoped I would avoid voice surgery.

I worked with Seattle Voice Lab.

I practised.

I tried.

I got frustrated.

And I became disappointed in myself.

I thought I was just bad at it.

By around March or April 2026, I had begun thinking:

I am probably going to have to operate on this.

Later it turned out that I had an unusual congenital problem in my larynx and extremely abnormal airflow characteristics.

That changed how I looked back on the whole thing.

I had spent months thinking I was failing at something that, anatomically, was going to be unusually difficult for me in the first place.

I have written separately about choosing VFSRAC and going to Yeson in Seoul:

The surgery was on 15 July 2026.

Physically, compared with everything else?

Nothing.

A walk in the park.

I was discharged the same day.

The hard part was the silence afterwards and the slow recovery.

What shocked me came later.

I played a video recently that I had recorded the day before surgery.

Oh my God.

My voice sounded so male.

I had not understood quite how male it sounded.

What should have told me was the reaction I used to get in public.

I would walk up to a counter.

Someone would greet me normally.

Then I would speak.

And I could see the tiny flicker of recognition.

Oh. You’re transgender.

When I was completely mute after surgery, that stopped happening.

Which was a fairly useful accidental experiment.

Now I am speaking again.

And increasingly, that reaction does not appear to be coming back.

Yesterday was the first day where the voice came out of my mouth almost exactly the way I had hoped it eventually would.

Softer.

Sweeter.

Not forced.

And I thought:

Wow. I think we’re getting there.

What would I actually change?

The obvious retrospective lesson would be:

You moved too quickly.

Slow down.

Take your time.

Spend years finding yourself.

Oddly, that is not my conclusion.

For me, moving quickly was one of the decisions I would make again.

There are things I would change.

I might have done the face before the body surgery because the face mattered more to me than anything else.

Although, ironically, doing the tummy tuck first may actually have helped the overall schedule because I needed recovery time before vaginoplasty anyway.

I probably would have added breast augmentation to that first Turkish operation.

I would probably have booked the voice surgery earlier.

I might have asked for the facelift to be slightly tighter.

These are details.

What strikes me more when I look back is how modest my original expectations were.

I genuinely believed that perhaps, after all this, strangers would look at me and think:

Yes, probably transgender.

But she looks all right.

That was my dream.

The outcome exceeded that dream.

I’m allowed to be pleased about that without pretending it means there is some universal formula behind it.

The thing I thought I would have to learn

Another thing I got wrong was mannerisms.

I genuinely assumed I would have to learn how to move like a woman.

How to sit.

How to gesture.

How to hold myself.

Somewhere in my head, I had created another entire training programme.

Then I started watching myself on video.

And realised:

Oh.

A lot of it is already there.

That was one of the stranger discoveries.

I had expected femininity to involve much more conscious performance than it actually did for me.

Instead, quite a lot of what I thought I would have to construct simply appeared once I stopped suppressing it.

Money

There is an important caveat to everything I have written here.

I had a financial advantage that many people do not have.

Cost did not dictate my choice of surgeon.

That obviously changes the available options enormously.

And even with that advantage, transition cost an astonishing amount of money.

I have never added it up.

I don’t want to add it up.

It isn’t only surgery.

Flights.

Hotels.

Consultations.

Clothes.

Makeup.

Laser.

Electrolysis.

Skin.

Treatments.

Everything.

It is a bloody fortune.

I would prefer not to know the number.

The other cost

The financial cost was not the most important one.

My transition cost me almost everybody in my life.

I had to start again.

Some relationships are slowly rebuilding.

Some are not.

There are people who were once extremely close to me who have never come back and may never come back.

That belongs in any honest account of what happened.

I don’t want to turn this article into an analysis of those relationships, so I will leave it there.

When transition stopped being the main project

Something changed around March this year.

Transition stopped being the main thing in my life.

Not because there was nothing left to do.

It just lost first place.

And what replaced it?

Work.

Obviously.

The crazy bitch who works fourteen hours a day came back.

Technology.

Software.

Learning.

Building.

Ideas.

Trying to understand things nobody has asked me to understand.

I basically moved from one obsession to another.

And strangely, that made me realise how much of me had stayed exactly the same.

All the things I genuinely liked about myself before transition were still there.

Technology.

Finance.

Exercise.

Learning.

Improving myself.

Building things.

The difference was that I was calmer.

Less angry at the world.

I used to spend an enormous amount of time trying to understand everything outside myself.

Politics.

People.

Systems.

The entire bloody universe.

Looking outward, perhaps partly because it stopped me looking inward.

I don’t do that nearly as much now.

I am also less interested in material accumulation.

I still have ridiculous ambition about doing things.

Achievement still matters enormously to me.

But bigger house, bigger car, bigger everything?

Not so much.

The idea of living in an enormous house now sounds exhausting.

Five bathrooms?

Why?

I’ll have one, thank you very much.

In some strange way, transition did not destroy the person I had been.

It made me a happy Stephen David Bennett.

That sentence probably sounds odd.

But it is what I mean.

Same person.

Much more peaceful.

Age

I also want to look young.

There.

Like practically every other woman, I would quite like time to stop attacking my face.

I was never under any illusion that I was going to transition in my fifties and emerge looking 25.

But I absolutely wanted to look good for my age.

Hormones changed things.

Skin treatments changed things.

The facelift changed things.

Fat grafting changed things.

The whole face changed things.

If somebody asks me what my anti-ageing secret is, I do not pretend it is green juice and positive thinking.

My standard answer is:

Seventeen hours of plastic surgery.

RibXcar

There is one more thing I am considering.

RibXcar.

I am speaking to a surgeon in Poland on 9 Octobe

r

Do I need it?

No.

That is the difference.

The face felt urgent.

Bottom surgery became urgent.

The voice felt urgent.

Rib surgery does not.

It sits in a completely different category.

Nice to have.

I just want to look fucking snatched.

That, more than anything, is probably how I know I am approaching the end.

I may have another facelift when I am in my early sixties.

The first one was done alongside enormous skeletal changes, so there was always going to be an element of judgement about how aggressively to tighten everything before all the swelling had settled and the bones had found their final position.

If I have another one later, I would not really count that as transition.

That is just ordinary vanity.

Gravity can still fuck off.

One year later

Yesterday was the first anniversary of the second and biggest day of my facial surgery.

One year.

And a huge amount has happened since then.

My face has finally settled.

My voice is beginning to arrive.

The enormous items on the Kanban board have mostly disappeared.

My work has taken over my brain again.

I am about to appear on Heroines of My Life, which still feels faintly surreal given that I once looked at women on sites like that and wondered whether I could ever get anywhere close.

And yet there is one thing that has not happened as quickly as I thought it would.

Last week I recorded another video.

In it, I said something like:

I cannot fucking believe how often the word transgender still appears in my day.

Still.

In conversations.

In my thoughts.

In things I read.

In things I write.

In the way I analyse myself.

I thought that by now it would have faded further into the background.

It hasn’t.

Not yet.

And I cannot wait for it to.

Not because I am ashamed of being transgender.

Not because I want to rewrite my history.

I just don’t want it to remain the organising principle of my life.

Maybe transition doesn’t end with the final operation.

Maybe it doesn’t end when your face settles.

Maybe it doesn’t end when your voice changes.

Maybe it ends on some utterly unremarkable Tuesday when you suddenly realise:

I haven’t thought about being transgender for a day.

I think I would like that.

Until then, there is still some electrolysis.

A voice to finish rehabilitating.

Possibly some ribs to rearrange.

And, finally, rather more life than transition to get on with.

A few people have asked me a perfectly reasonable question.

You’re a software engineer. You’ve spent years building software products for clients and being paid to deliver them.

And now you appear to have developed a machine that can build software at a frankly rather frightening rate.

Well, always one to have a Dick Dastardly plan up my sleeve. Relay is going to be a lot more than a software development tool. Read on…

Relay can architect things, break them into work, dispatch engineers, review what comes back, test it, reject bad work, fix things, integrate everything and keep going. We’re approaching the point where producing three or four functioning software systems in a day doesn’t sound completely ridiculous anymore.

Which raises an obvious question.

Why the fuck would anybody need to do that?

Who needs four software systems a day?

What’s the commercial point?

What exactly am I planning to do with this bloody thing?

And I think I’ve done a slightly poor job of explaining the answer, because Relay isn’t really about producing software quickly.

That’s just one third of it.

The bigger idea is closer to an automated venture studio. Or, in some respects, a venture capital company which can make hundreds of tiny investments, except instead of primarily investing money into other people building companies, the machine can discover the opportunity, investigate it, build the product, take it to market and then decide whether to keep investing in it.

That’s the actual thesis.

And it starts from an assumption which is hardly revolutionary anymore:

The cost of creating software is collapsing.

We all know this.

You don’t need another article from a software engineer breathlessly announcing that AI can write code.

Yes. It can.

Next.

The interesting question is what happens after that becomes normal.

Because if producing the software itself stops being the expensive part, the economics of starting digital businesses change rather dramatically.

And that’s what I’m building Relay to exploit.

The software isn’t the system

For most of my career, software production was the enormous constraint.

Somebody had an idea. Then you needed developers, architects, testers, infrastructure people, product managers and somebody to manage everybody else.

Then meetings.

Obviously meetings.

Possibly even meetings to discuss why the previous meeting hadn’t resulted in anything actually being built.

Eventually, after spending £100,000 or £500,000 or £2 million, some software might appear.

That meant you couldn’t pursue every vaguely interesting idea.

You had to choose.

And you had to choose bloody carefully.

AI is making that constraint disappear remarkably quickly.

But here’s the thing.

If software costs almost nothing to produce, that doesn’t mean opportunity costs almost nothing to find.

The difficult things become everything around the software.

Which markets are worth entering?

What problems are actually painful enough that people will pay to solve them?

What regulatory change has just created a new requirement?

What tiny community is currently fighting with spreadsheets because nobody has bothered building the obvious tool?

Is there distribution?

How many customers exist?

What are they worth?

Can you reach them?

Are you three years too early?

Six months too late?

Is there already somebody much better?

Are people complaining loudly enough that a business might exist?

And, inevitably, are you lucky?

Those become the scarce resources.

So Relay isn’t intended merely to industrialise software creation.

The eventual system industrialises the entire process of finding, creating and testing businesses.

There are three parts.

1. Discovery

The first part barely exists today.

It’s opportunity discovery.

Think R&D, market research and a slightly deranged investment analyst rolled into one.

There will be looping research agents whose entire job is to go hunting.

New markets.

Bad existing products.

Regulatory changes.

New APIs.

Search trends.

Industry complaints.

Communities with unsolved problems.

Changes in technology.

New ways of combining things which weren’t economically viable twelve months ago.

Potential opportunities enter a funnel.

Then other processes attack them.

How many potential users are there?

What do they currently use?

How much do they currently pay?

Who are the competitors?

How hard would it be to reach customers?

What’s the support burden?

What’s the regulatory exposure?

What’s the realistic revenue at 0.1%, 1% or 5% penetration?

How expensive would this thing be to build and operate?

Most ideas should die here.

In fact, I want an absolute massacre.

A thousand possibilities might become fifty serious investigations.

Fifty might become five.

And perhaps one gets built.

That isn’t failure.

That’s the machinery working.

Traditional venture capital operates on a related principle. You don’t expect every investment to become enormous. You build a portfolio because the returns are asymmetric: a small number of exceptional winners can pay for an awful lot of losers.

I’m applying something similar much earlier in the chain.

Except rather than waiting for entrepreneurs to bring opportunities to me, I want machinery continuously looking for them.

2. Relay

Then the survivors reach Relay.

Relay is the factory.

This is the bit I’ve been obsessively building.

It contains the engineering organisation: architects, workers, reviewers, publishers, governance, work decomposition, memory, escalation, testing and all the assorted machinery required to stop autonomous AI agents wandering around setting fire to things.

Once an opportunity has survived the research funnel, Relay gets a wonderfully simple instruction:

Build the bloody thing.

Not prepare a twelve-month roadmap.

Not create a 73-slide PowerPoint presentation about the transformational potential of the initiative.

Build it.

Put it somewhere people can use it.

Then find out whether the original hypothesis was right.

This is where extremely high software throughput suddenly makes commercial sense.

I don’t actually need four new software products every day.

I need the ability to produce four because that means the cost of testing each opportunity becomes tiny.

And that fundamentally changes what constitutes a viable opportunity.

3. Imprint

Then comes the third part.

Imprint.

Software engineers have a wonderful habit of believing that if they build something sufficiently clever, humanity will somehow detect its existence through vibrations in the Earth’s crust.

Unfortunately, this does not appear to be how markets work.

Somebody has to distribute the bloody thing.

That’s Imprint.

Imprint is the outreach and distribution organisation.

Instagram.

Reddit.

YouTube.

SEO.

Email.

Partnerships.

Community outreach.

Landing pages.

Tutorials.

Advertising experiments.

Articles.

Videos.

Hundreds or potentially thousands of small attempts to put a product in front of the people who might care about it.

But Imprint isn’t merely a marketing department endlessly pumping content onto the internet.

Its most important output is signal.

This audience responded.

That one didn’t.

This Reddit post generated twenty registrations.

That Instagram reel generated absolutely bugger all.

People are signing up but not paying.

People keep requesting the same feature.

We thought accountants wanted this, but for some inexplicable reason German dentists appear to be going berserk for it.

Those signals return to the system.

And that’s where the three pieces become one thing.

The loop is the product

Discovery finds something.

Relay builds it.

Imprint pushes it into the world.

The world responds.

Those responses become signals.

Relay changes the product.

Imprint changes the message.

Discovery recalculates whether the opportunity still deserves investment.

Then it goes around again.

Discover → analyse → build → distribute → measure → learn → reinvest or kill.

That’s Relay.

Or at least that’s what Relay is becoming.

And this is why merely saying “AI makes software cheaper” misses the interesting part.

Cheap software is just the enabling condition.

The actual opportunity is what you can build around that fact.

You don’t have to be right very often

This might be the part that excites me most.

Conventional software economics force you to be right quite a lot.

If every attempt costs £500,000, you cannot casually test twenty ideas.

But suppose the cost falls by two orders of magnitude.

Now you can be wrong.

A lot.

And being allowed to be wrong is incredibly powerful.

I don’t necessarily need a magical AI capable of identifying the next billion-dollar company with prophetic accuracy.

I’d actually be deeply suspicious of anybody claiming to possess one.

I need something much less glamorous.

I need a machine capable of finding plausible opportunities cheaply enough that we can test a lot of them.

That’s essentially portfolio theory applied to building businesses.

Some go immediately to zero.

Fine.

Some survive but never become particularly exciting.

Fine.

Some become small profitable products.

Lovely.

And perhaps occasionally one goes absolutely fucking bananas.

That’s where the return comes from.

The machine doesn’t have to predict the winner perfectly.

It just has to keep producing sufficiently cheap bets.

Small suddenly becomes interesting

And collapsing development costs do something else.

They make markets interesting which traditional software companies wouldn’t touch.

Imagine a software product capable of making €8,000 a month.

For a conventional funded startup, that’s barely worth getting out of bed for.

You’ve got engineers, managers, salespeople, offices, SaaS subscriptions, investors and an expensive espresso machine to pay for.

But if that €8,000 product cost almost nothing to create and requires almost no human labour to operate?

That’s a lovely little business.

Now have fifty of them.

This is where the venture-capital analogy actually becomes rather useful.

I’m not necessarily looking for one company which consumes every resource I possess.

I’m thinking in terms of a portfolio.

Except instead of owning shares in fifty companies, the system can potentially create and operate the fifty companies itself.

And because the cost base is radically different, the minimum viable market becomes radically smaller too.

There could be thousands upon thousands of profitable little niches which historically weren’t worth serving because the economics of software development made them ridiculous.

Those become interesting again.

So that’s the actual plan

That’s why I’m building Relay.

Not because the world desperately needs a machine capable of producing four software systems before lunch.

That would be an extraordinarily stupid objective on its own.

I’m building the engineering machinery because it sits in the middle of something much bigger.

Discovery finds opportunities.

Relay turns them into reality.

Imprint puts them into the world and listens to what comes back.

Then the whole thing reallocates its effort based on what it learns.

It’s part software factory, part R&D organisation, part marketing operation, part venture studio and, in a slightly peculiar sense, part venture capital portfolio.

The long-term objective is not:

“Build software incredibly quickly.”

It’s:

“Continuously discover potentially profitable things, test them incredibly cheaply, and invest more heavily in the ones which show signs of life.”

Maybe it doesn’t work.

Entirely possible.

I may ultimately discover that I’ve spent an extraordinary amount of effort constructing the world’s most sophisticated autonomous machine for producing software nobody wants.

There would be something magnificently appropriate about that.

But that’s the bet.

Software becoming cheap isn’t the destination.

It’s the starting gun.

Because once execution becomes cheap enough, you don’t need to make one enormous bet.

You can make hundreds of tiny ones.

And that’s my slightly deranged Dick Dastardly, rubbing-my-hands-together-in-the-corner plan.

Relay isn’t being built so that I can create four software products a day.

It’s being built so that, eventually, I can afford for three of them to be wrong.

A few people have asked me a perfectly reasonable question.

You’re a software engineer. You’ve spent years building software products for clients and being paid to deliver them.

And now you appear to have developed a machine that can build software at a frankly rather frightening rate.

Well, always one to have a Dick Dastardly plan up my sleeve. Relay is going to be a lot more than a software development tool. Read on…

Relay can architect things, break them into work, dispatch engineers, review what comes back, test it, reject bad work, fix things, integrate everything and keep going. We’re approaching the point where producing three or four functioning software systems in a day doesn’t sound completely ridiculous anymore.

Which raises an obvious question.

Why the fuck would anybody need to do that?

Who needs four software systems a day?

What’s the commercial point?

What exactly am I planning to do with this bloody thing?

And I think I’ve done a slightly poor job of explaining the answer, because Relay isn’t really about producing software quickly.

That’s just one third of it.

The bigger idea is closer to an automated venture studio. Or, in some respects, a venture capital company which can make hundreds of tiny investments, except instead of primarily investing money into other people building companies, the machine can discover the opportunity, investigate it, build the product, take it to market and then decide whether to keep investing in it.

That’s the actual thesis.

And it starts from an assumption which is hardly revolutionary anymore:

The cost of creating software is collapsing.

We all know this.

You don’t need another article from a software engineer breathlessly announcing that AI can write code.

Yes. It can.

Next.

The interesting question is what happens after that becomes normal.

Because if producing the software itself stops being the expensive part, the economics of starting digital businesses change rather dramatically.

And that’s what I’m building Relay to exploit.

The software isn’t the system

For most of my career, software production was the enormous constraint.

Somebody had an idea. Then you needed developers, architects, testers, infrastructure people, product managers and somebody to manage everybody else.

Then meetings.

Obviously meetings.

Possibly even meetings to discuss why the previous meeting hadn’t resulted in anything actually being built.

Eventually, after spending £100,000 or £500,000 or £2 million, some software might appear.

That meant you couldn’t pursue every vaguely interesting idea.

You had to choose.

And you had to choose bloody carefully.

AI is making that constraint disappear remarkably quickly.

But here’s the thing.

If software costs almost nothing to produce, that doesn’t mean opportunity costs almost nothing to find.

The difficult things become everything around the software.

Which markets are worth entering?

What problems are actually painful enough that people will pay to solve them?

What regulatory change has just created a new requirement?

What tiny community is currently fighting with spreadsheets because nobody has bothered building the obvious tool?

Is there distribution?

How many customers exist?

What are they worth?

Can you reach them?

Are you three years too early?

Six months too late?

Is there already somebody much better?

Are people complaining loudly enough that a business might exist?

And, inevitably, are you lucky?

Those become the scarce resources.

So Relay isn’t intended merely to industrialise software creation.

The eventual system industrialises the entire process of finding, creating and testing businesses.

There are three parts.

1. Discovery

The first part barely exists today.

It’s opportunity discovery.

Think R&D, market research and a slightly deranged investment analyst rolled into one.

There will be looping research agents whose entire job is to go hunting.

New markets.

Bad existing products.

Regulatory changes.

New APIs.

Search trends.

Industry complaints.

Communities with unsolved problems.

Changes in technology.

New ways of combining things which weren’t economically viable twelve months ago.

Potential opportunities enter a funnel.

Then other processes attack them.

How many potential users are there?

What do they currently use?

How much do they currently pay?

Who are the competitors?

How hard would it be to reach customers?

What’s the support burden?

What’s the regulatory exposure?

What’s the realistic revenue at 0.1%, 1% or 5% penetration?

How expensive would this thing be to build and operate?

Most ideas should die here.

In fact, I want an absolute massacre.

A thousand possibilities might become fifty serious investigations.

Fifty might become five.

And perhaps one gets built.

That isn’t failure.

That’s the machinery working.

Traditional venture capital operates on a related principle. You don’t expect every investment to become enormous. You build a portfolio because the returns are asymmetric: a small number of exceptional winners can pay for an awful lot of losers.

I’m applying something similar much earlier in the chain.

Except rather than waiting for entrepreneurs to bring opportunities to me, I want machinery continuously looking for them.

2. Relay

Then the survivors reach Relay.

Relay is the factory.

This is the bit I’ve been obsessively building.

It contains the engineering organisation: architects, workers, reviewers, publishers, governance, work decomposition, memory, escalation, testing and all the assorted machinery required to stop autonomous AI agents wandering around setting fire to things.

Once an opportunity has survived the research funnel, Relay gets a wonderfully simple instruction:

Build the bloody thing.

Not prepare a twelve-month roadmap.

Not create a 73-slide PowerPoint presentation about the transformational potential of the initiative.

Build it.

Put it somewhere people can use it.

Then find out whether the original hypothesis was right.

This is where extremely high software throughput suddenly makes commercial sense.

I don’t actually need four new software products every day.

I need the ability to produce four because that means the cost of testing each opportunity becomes tiny.

And that fundamentally changes what constitutes a viable opportunity.

3. Imprint

Then comes the third part.

Imprint.

Software engineers have a wonderful habit of believing that if they build something sufficiently clever, humanity will somehow detect its existence through vibrations in the Earth’s crust.

Unfortunately, this does not appear to be how markets work.

Somebody has to distribute the bloody thing.

That’s Imprint.

Imprint is the outreach and distribution organisation.

Instagram.

Reddit.

YouTube.

SEO.

Email.

Partnerships.

Community outreach.

Landing pages.

Tutorials.

Advertising experiments.

Articles.

Videos.

Hundreds or potentially thousands of small attempts to put a product in front of the people who might care about it.

But Imprint isn’t merely a marketing department endlessly pumping content onto the internet.

Its most important output is signal.

This audience responded.

That one didn’t.

This Reddit post generated twenty registrations.

That Instagram reel generated absolutely bugger all.

People are signing up but not paying.

People keep requesting the same feature.

We thought accountants wanted this, but for some inexplicable reason German dentists appear to be going berserk for it.

Those signals return to the system.

And that’s where the three pieces become one thing.

The loop is the product

Discovery finds something.

Relay builds it.

Imprint pushes it into the world.

The world responds.

Those responses become signals.

Relay changes the product.

Imprint changes the message.

Discovery recalculates whether the opportunity still deserves investment.

Then it goes around again.

Discover → analyse → build → distribute → measure → learn → reinvest or kill.

That’s Relay.

Or at least that’s what Relay is becoming.

And this is why merely saying “AI makes software cheaper” misses the interesting part.

Cheap software is just the enabling condition.

The actual opportunity is what you can build around that fact.

You don’t have to be right very often

This might be the part that excites me most.

Conventional software economics force you to be right quite a lot.

If every attempt costs £500,000, you cannot casually test twenty ideas.

But suppose the cost falls by two orders of magnitude.

Now you can be wrong.

A lot.

And being allowed to be wrong is incredibly powerful.

I don’t necessarily need a magical AI capable of identifying the next billion-dollar company with prophetic accuracy.

I’d actually be deeply suspicious of anybody claiming to possess one.

I need something much less glamorous.

I need a machine capable of finding plausible opportunities cheaply enough that we can test a lot of them.

That’s essentially portfolio theory applied to building businesses.

Some go immediately to zero.

Fine.

Some survive but never become particularly exciting.

Fine.

Some become small profitable products.

Lovely.

And perhaps occasionally one goes absolutely fucking bananas.

That’s where the return comes from.

The machine doesn’t have to predict the winner perfectly.

It just has to keep producing sufficiently cheap bets.

Small suddenly becomes interesting

And collapsing development costs do something else.

They make markets interesting which traditional software companies wouldn’t touch.

Imagine a software product capable of making €8,000 a month.

For a conventional funded startup, that’s barely worth getting out of bed for.

You’ve got engineers, managers, salespeople, offices, SaaS subscriptions, investors and an expensive espresso machine to pay for.

But if that €8,000 product cost almost nothing to create and requires almost no human labour to operate?

That’s a lovely little business.

Now have fifty of them.

This is where the venture-capital analogy actually becomes rather useful.

I’m not necessarily looking for one company which consumes every resource I possess.

I’m thinking in terms of a portfolio.

Except instead of owning shares in fifty companies, the system can potentially create and operate the fifty companies itself.

And because the cost base is radically different, the minimum viable market becomes radically smaller too.

There could be thousands upon thousands of profitable little niches which historically weren’t worth serving because the economics of software development made them ridiculous.

Those become interesting again.

So that’s the actual plan

That’s why I’m building Relay.

Not because the world desperately needs a machine capable of producing four software systems before lunch.

That would be an extraordinarily stupid objective on its own.

I’m building the engineering machinery because it sits in the middle of something much bigger.

Discovery finds opportunities.

Relay turns them into reality.

Imprint puts them into the world and listens to what comes back.

Then the whole thing reallocates its effort based on what it learns.

It’s part software factory, part R&D organisation, part marketing operation, part venture studio and, in a slightly peculiar sense, part venture capital portfolio.

The long-term objective is not:

“Build software incredibly quickly.”

It’s:

“Continuously discover potentially profitable things, test them incredibly cheaply, and invest more heavily in the ones which show signs of life.”

Maybe it doesn’t work.

Entirely possible.

I may ultimately discover that I’ve spent an extraordinary amount of effort constructing the world’s most sophisticated autonomous machine for producing software nobody wants.

There would be something magnificently appropriate about that.

But that’s the bet.

Software becoming cheap isn’t the destination.

It’s the starting gun.

Because once execution becomes cheap enough, you don’t need to make one enormous bet.

You can make hundreds of tiny ones.

And that’s my slightly deranged Dick Dastardly, rubbing-my-hands-together-in-the-corner plan.

Relay isn’t being built so that I can create four software products a day.

It’s being built so that, eventually, I can afford for three of them to be wrong.

Most people who encounter me now probably think I am a fairly confident, capable and presumably quite popular human being.

Professionally, online, through Fast Track Fem, and through the various strange corners of my life I seem to have accumulated, that is probably the version of me people see.

Hell, last weekend I ended up on stage in Wild nightclub doing a Katy Perry impersonation with the drag queens.

They did ask who wanted to do it.

“Me,” I said, obviously.

But I have also made no secret whatsoever of the fact that after I transitioned, almost everybody from my previous life wanted absolutely nothing to do with me.

And I mean almost everybody.

My marriage ended. My children wanted little or nothing to do with me. Friends disappeared. Family disappeared. At one point I was left with about two people, and one of them was my mother.

That is quite an extraordinary thing to happen to a human being.

And I have spent an enormous amount of time trying to understand why.

There is, of course, an obvious explanation available: transphobia.

And with some people, I am sure that is part of it. There are people who have a visceral dislike of the whole idea of somebody being transgender.

Oddly, I am not particularly exercised by that.

I don’t think everybody has to agree with the concept. I don’t think everybody has to believe that I am a woman. They can think whatever they like. I have said that many times before.

But I don’t think transphobia explains most of what happened to me.

Because I suspect many of the same people who wanted nothing to do with me would be perfectly pleasant to a transgender colleague. They might work with her. Befriend her. Go for a drink with her. They might even consider themselves completely accepting.

With me, it was different.

And I have thought about that difference over and over again.

Why?

Why did so many people who had loved me, liked me, lived with me, grown up with me or known me for decades turn away so completely?

I think, eventually, I arrived at the answer.

One word.

Choice.

They believe I made one.

And the uncomfortable thing is this:

I think they’re right.

That is the case against me.

I had a wife. I had children. I had a family. I had friends. I had a house, a career and a life which, from the outside, looked not merely functional but pretty successful.

Then I transitioned.

And the consequences were catastrophic.

I wasn’t an idiot. I understood perfectly well that I was pulling a pin from something extraordinarily complicated.

I knew my marriage might not survive. I knew my children might struggle with it. I knew my family might react badly. I knew friendships could disappear.

I didn’t wake up one Tuesday morning, put on some lipstick and think, Christ, I wonder what will happen now.

I knew there was risk.

And there is therefore a version of events which is simple, coherent and, on the face of it, pretty damning.

Stevie chose herself.

She had responsibilities to other people, particularly her children, and she chose what she wanted instead.

I know that argument very well because I have made it against myself approximately four million times.

I also know that quite a few people from my old life read what I write.

They would never dream of telling me, obviously.

They would apparently rather gnaw through their own forearm.

But they do.

I’m not stupid.

So I don’t particularly want to construct a comforting little courtroom in which I appoint myself judge, jury and glamorous middle-aged defendant, dismiss all charges, congratulate myself on my bravery and then go for lunch.

I think the prosecution has a case.

I made a choice.

And that is precisely why I have such difficulty with one of the standard stories we tell about transition.

“I had no choice.”

We have all heard versions of it.

I was a woman trapped in a man’s body.

I had gender dysphoria.

I had to transition.

There was no alternative.

And I understand why that story exists. It does a tremendous amount of moral heavy lifting.

If I genuinely had no choice, then there isn’t really much left to discuss.

Nobody has to ask what I owed my wife.

Nobody has to ask what I owed my children.

Nobody has to ask whether I was entitled to cause enormous pain to other people in order to stop living in a way that caused enormous pain to me.

If there was no choice, there was no decision.

Something happened to me.

I responded.

End of story.

But I don’t think that is true of me.

I did have another choice.

I could have carried on.

In fact, I have unusually good evidence that this was possible because I had already done it for decades.

I had wanted to be female for as long as I can remember.

I had spent an enormous part of my life negotiating with that fact, suppressing it, indulging it privately, becoming frightened by it, putting it back in its box and then discovering several years later that the bloody thing had escaped again.

But I functioned.

More than functioned, really.

I made money. I built a career. I got married. I became a father. I wrote software. I paid bills. I went to school events. I did children’s birthdays and family holidays and all the other things society generally uses as evidence that somebody is getting on perfectly well with being alive.

I wasn’t going to drop dead if I didn’t transition.

That matters to me because I don’t want to retrospectively turn my life into a medical emergency simply because doing so would make the story morally cleaner.

And I have never been particularly fond of the way the phrase “gender dysphoria” is sometimes used as though it explains everything.

It is a useful clinical term. I understand what it means.

But sometimes it feels less like an explanation and more like a full stop.

Why did you transition?

Gender dysphoria.

Ah. Very good. Case closed.

Except what did that actually mean?

For me, it meant that I wanted, with extraordinary persistence, to be a woman.

I wanted my body to be female.

I wanted to move through the world as a woman.

I wanted other people to see me that way.

And I wanted it badly enough that the desire survived decades of negotiation, denial, distraction, work, marriage, children, money and every other thing I threw at it.

You can call that dysphoria if you like.

But giving something a clinical name doesn’t magically remove the question of choice.

Which brings me, somewhat unexpectedly, to Torremolinos.

Buying a flat in Torremolinos is a choice.

Walking out of a burning building is also a choice.

Technically, you can remain in the burning building.

Nobody has removed your free will. You can sit on the sofa while the curtains catch fire and maintain a principled commitment to staying exactly where you are.

But nobody would describe those two decisions as belonging to the same category.

Nobody says, “Well, she chose to leave the burning building, didn’t she? She could have stayed.”

The interesting choices in life are usually somewhere between Torremolinos and the burning building.

Most of life happens there.

Someone leaves a miserable marriage. They could have stayed.

Someone walks away from a career that is destroying them. They could have carried on.

Someone comes out.

Someone leaves the religion they were raised in.

Someone emigrates.

Someone decides not to spend another twenty years living according to expectations which make everybody around them comfortable.

There is nearly always another available option.

The important question is what that option costs.

And I think this is where the word “choice” becomes dangerously slippery.

Because we often judge somebody’s decision by looking only at the thing they chose.

We don’t look closely enough at the thing they rejected.

I could have remained Stephen.

That sentence is true.

I had the necessary clothes.

I had the passport.

I had an established social identity and decades of experience performing the role.

I was actually rather good at it.

What I don’t know is what another twenty or thirty years of doing it would have cost me.

And that is where the neat moral arithmetic starts to fall apart.

Because now there are two sets of suffering.

Mine and theirs.

If transition made my life more bearable but made the lives of people I loved less bearable, how exactly are we supposed to calculate that?

Do I get priority because it is my life?

Do my children get priority because I brought them into the world and therefore accepted obligations which should outrank my desire for personal fulfilment?

Does my wife get priority because she married one person and was entitled to expect some basic continuity in the bargain?

How unhappy was I required to become before I had permission to change things?

How much of yourself are you morally required to sacrifice for the people you love?

There is an extremely seductive answer to that last question.

Everything.

Parents sacrifice for children.

Partners sacrifice for one another.

Families work because people constantly suppress what they would individually prefer for the benefit of the whole.

Civilisation would collapse fairly rapidly if everybody woke up tomorrow morning and announced that they were going to live their authentic truth regardless of who had to pick up the pieces.

I believe in responsibility.

Which is inconvenient, because responsibility is a much easier principle to hold when it is somebody else who has to make the sacrifice.

But there has to be a limit.

There has to be some point at which a life belongs, at least partly, to the person living it.

Otherwise we arrive at a fairly grotesque principle.

Once enough people depend upon a particular version of you, you acquire a moral duty to remain that person indefinitely.

Even if maintaining it requires you constantly to suppress something fundamental about yourself.

Even if the person everyone wants you to remain is becoming increasingly difficult for you to inhabit.

Even if everybody else gets the version of your life they want because you have agreed not to have yours.

That doesn’t make leaving painless.

It doesn’t make the damage unreal.

And it certainly doesn’t mean the people who were hurt are required to applaud.

This is perhaps what frustrates me about both of the simple stories we tell about transition.

One removes choice altogether.

No choice. No responsibility. Nothing to discuss.

The other treats it as completely ordinary choice.

You wanted something. You chose it. Your family paid the price.

I don’t believe either describes what happened.

I chose.

But a choice can be real without the alternatives being equal.

A choice can be technically available while carrying a cost that nobody else can see.

And acknowledging that I made a decision doesn’t require me to pretend that remaining exactly as I was would have been a neutral option with no consequences of its own.

Perhaps that is the thing I wish some people from my old life understood.

Not that they were wrong to be hurt.

Not even necessarily that they were wrong to be angry.

Just that the choice they think I made may not be the choice I experienced.

From their side, there were two doors.

Behind one was the existing family, the existing marriage, the existing person.

Behind the other was transition.

And I walked through the second one.

From their side, I can understand how brutal that looks.

What they could not see was what was written on the first door.

And perhaps neither could I, fully.

I once came across an idea that has stayed with me ever since.

At the end of your life, there are only two people you really need to please.

You at eight.

And you at eighty.

It sounds like the sort of sentence somebody sticks over a photograph of a mountain on Instagram, which should immediately make me hate it.

Unfortunately, I don’t.

I think about it all the time.

The eight-year-old version of you, before the compromises, the bills, the sensible decisions and the careful construction of an adult life.

And the eighty-year-old version, looking backwards, when there is very little time left for bullshit.

I think I can face those two people.

The little boy I was would be astonished by me.

Not just because I eventually became the woman he so desperately wanted to be.

He would recognise everything else too.

The endless love of cycling. The obsession with computers. The need to build things, fiddle with things and make things work. He built dens, go-karts and ridiculous contraptions with CB radios attached to them. Then computers arrived, I started coding, and in many ways I never really stopped doing the same thing.

I did not destroy the person I was.

I became even more the person I was.

I think he would recognise that immediately.

The wanting. The making. The tinkering. The curiosity. The refusal to leave things alone when they could be rebuilt into something better.

I carried all of it with me.

I saw it through.

And the eighty-year-old woman?

I hope I get to meet her.

I don’t think she will let me pretend nobody was hurt.

I don’t think she will let me rewrite the past into a comforting story in which I had no agency and therefore no responsibility.

I think she will see the wreckage as well as the victories.

But I hope she will think I was brave.

I hope she will think that eventually, after an absurd amount of hesitation, I accepted that this was also my life.

Maybe that is selfish.

Maybe, at some level, every serious act of self-preservation is.

But I no longer think the opposite of selfishness is necessarily goodness.

Sometimes it is simply disappearance.

So yes.

I had a choice.

I think that is what makes the decision morally interesting.

And I think I made the right one.

And as I have already said, there will be people from my old life who read this.

I would bet my bottom dollar that at least one of them will get to the end and say:

“Yes, but you still had a bloody choice.”

To which I would answer:

You didn’t read the bloody essay.