2026

I’m sitting here tonight watching Home Alone 2.

I couldn’t find it on Netflix or any of the usual places, so I assumed it wasn’t available. Then, by chance, I found it on Channel 4 Player and put it on. And it’s been an absolute joy.

I love John Hughes films. I always have. I’ve got Ferris Bueller on the wall in my office. Those films are deeply embedded in me. They touch something playful, optimistic, mischievous, and emotionally literate that a lot of people simply don’t have. Hughes understood that part of the human psyche, and his films reach it effortlessly.

Watching it tonight reminded me of something else.

The last time I went to Manhattan, the last time I walked through Central Park, was at the absolute zenith of Steve’s financial power. That was about three years ago now. At the time, I was worth millions. Actual millions. I’d been clever. I’d stacked contracting clients, ridden Bitcoin properly, made disciplined decisions across multiple income streams.

And then I fucked it up. Properly.

I took too much risk. I misunderstood how those risks compounded. I lost vast amounts of money. The sort of losses that, for some people, are genuinely life-ending.

I didn’t jump off a bridge. I transitioned. That’s a joke. But it’s also not.

What that story doesn’t tell people is this: I didn’t get lucky the first time. I had methodology. I had systems. I had models. My entries weren’t the problem. My exits weren’t the problem. The ideas were sound. The signals were clever. The failure was risk management, not intelligence.

And the thing that took me from zero, from a council estate, to millions, is still sitting right where it always was. In my head.

2025 has been the most volatile, painful, astonishing, brutal, extraordinary year of my life. I don’t think anyone could reasonably dispute that.

I’ve been abandoned by much of my family.
I’ve gone from being a burly-looking man to being, frankly, an unignorable-looking woman.
I’ve gone from millions to effectively zero.

But I have not lost the things that mattered.

One of the great misunderstandings about my transition is the idea that it was impulsive, emotional, or vague. It wasn’t. It was one of the most structured, granular, systems-driven projects I have ever undertaken.

I didn’t say, “I want to be a woman” and hope for the best.

I broke it down into goals.
Into body parts.
Into objectives.

What will my skin look like?
How do I get my waist to a size 28?
What interventions achieve a female hairline?
What sequencing minimises in-between phases?
What does the finished state actually look like?

It was a plan. A serious one.

By the end of January, I will have had my vaginoplasty. At that point, Version 1.0 is complete. That plan is finished. There is no going back, and thank God for that.

And so here I am, watching Home Alone 2, and I can feel something else beginning.

A new plan.

The losses I’ve suffered will never be trivial. But they can be absorbed. They can be integrated. They don’t have to define the future. They become part of the story, not the ending.

Version 2.0 is starting to take shape.

And Version 2.0 is about refinement.

Perfecting Stevie. Not just aesthetically, but behaviourally. How I move. How I think. How I operate in the world. How I deploy energy. How I build again, but better.

Because here’s the thing some people don’t like to hear:

Stevie was Steve.
And Steve was capable of making serious money.

I know there are people in my old life who roll their eyes at me. People who describe themselves as “in finance” because they take wealthy clients to lunch and manage relationships. People who mock, who minimise, who quietly hope I’m finished.

Fuck that.

I built risk models. I connected global liquidity to volatility indices. I created indicators to algorithmically trade entries and exits. My work was technical, theoretical, and real. My failure was not stupidity. It was excess risk.

Those are very different things.

So 2026 is coming.

And I don’t feel weak now. I don’t feel petrified. The worst has already happened. The people who were going to leave have left. I can live with that.

As Bob Dylan sang, when you’ve got nothing, you’ve got nothing to lose. I understand that now, properly.

So I’m raising a glass to 2026.

And to every other transgender person reading this: we can do this. We really can. The world will not always believe in us. Sometimes it will actively doubt us.

One last thing. I want to say thank you to everyone who has read, listened to, and engaged with my Substack. I only started writing it about four months ago, with no real expectations at all, and somehow nearly 25,000 people have read pieces I’ve put out into the world. That genuinely astonishes me. The messages, the kindness, the thoughtful responses, and the quiet support from people I’ve never met have meant more to me than I can properly articulate. You’ve kept me going during moments when things were very dark. You really have. I’m deeply grateful to all of you, and I wish you a very happy new year

Stevie Ann Bennett xxx