Interview with Stevie Bennett - Part 3

Monika: You continued working in technology throughout all of this. Did transitioning change the way your colleagues treated you, particularly in an industry where you spent so much of your professional life being perceived as a man?

Stevie: When I first started going back for interviews, I was very nervous. The first one I did was around crypto and .NET development, my two specialities, and I thought, I should ace this. I didn't even get it. And I'll never know why. That's one of the things nobody warns you about. If you don't get the job, you'll never know whether or not it was that, because they're not going to tell you.
When I did go back to work, what I noticed is that people have a tendency to assume women will be sweeter, less combative. I find I'm treated with less suspicion, seen as somehow more honest. And because I'm not one of the boys any more, they don't feel as threatened by me in some ways. But I am the same uppity woman I ever was, and I think people quickly forget I'm transgender.

Monika: You have gone from quantitative trading and software architecture to writing very personal essays about transition, divorce, ageing, dating and surgery. What made you decide that your private experiences were worth putting on the internet for everyone to read?

Stevie: There are two answers really: the reason it started, and the reason it continued.
Monika: Let's start with the reason it started, then.

Stevie: It started when I came back from my first surgery, in Turkey. I was at home in my old house, my family had gone away on holiday without me, and I had a lot of time alone with the realisation that the people I loved might potentially never speak to me again. And then a darker thought arrived: what if I were to die? The story of who I was would be in other people's hands, and they could say some terrible things about me to my children. They could make me out to be some crazy lunatic who did this thing, and downplay who I actually was. I had this desperate need to write my story down. So I started from the very beginning, thinking, maybe my children won't get to read this now, but maybe one day they can see how all of this happened. A lot of the later material stayed private and was never published, not even on Fast Track Femme. But the earliest parts of my life I did publish, because they didn't affect my children and weren't personal about my marriage.
Monika: And the reason it continued?

Stevie: And then it continued for a different reason. I realised that writing essays was structuring my thoughts in ways I hadn't done before, which is quite good when you have ADHD, because it forces you to stay on one track, although I will admit some of my essays still go all over the place. Then, about four months ago, I started to think, I'm not just transgender, you know, I have other thoughts and other ideas. So I started writing about macroeconomics, trading and investing, AI, fitness, the new things in my life, and the remit changed to being, basically, Stevie's world. If anyone is interested in Stevie's world, that's the place to read it. I will flip from an article about being mute for a month straight to my thesis on global liquidity. And it's quite funny: some of my investment articles get double-digit reads, while something about gender-critical people can get thousands. But I give them all the same love.

 

"I do have a full memoir written."

 

Monika: For a lot of trans girls, loneliness can become a part of life. Did you ever feel that, or were you lucky enough to avoid it?

Stevie: People might assume from the outside that this isn't true for me, but I am extremely lonely. I lost everybody who meant anything to me, apart from my mum, and I had to start all over again. And although I'm doing an okay job of it, you can't replace relationships that lasted decades with ones that have lasted six months. So yes, I struggle. I will say that, considering what I've faced, I think I've done a good job of keeping myself on an even keel. I've written about falling off the wagon at times, on Fast Track Femme, and I'll be honest about it here too. It's still not easy.
My little chihuahua gives me a lot of joy right now. If anything happened to him, I would be devastated. And I'm fortunate that I'm pretty good on my own compared with most people. I do love my own company. But what I crave is that high level of conversational sparring and fun with somebody you're close to. I think that's possibly another reason why I write Fast Track Femme so much. It fills some of that gap.

Monika: Many trans women are writing their memoirs these days. Have you ever thought about writing your own book, and if so, what would its central message be?

Stevie: It's interesting, because I do have a full memoir written. I will never publish it. It contains too much about my wife and my children, and the absolute devastation that took place as things tore to pieces at the start of my transition. I would never share that with the world. It's too much. I have serialised the earlier chapters on Fast Track Femme, but I will never release probably three quarters of the book, because it covers their lives, and that's not fair.
At one point I did think about writing something else, a kind of transition blueprint, for want of a better phrase, because a lot of people have asked me how I did it, what my strategies were, and so on. But I've learned over time that not everybody's transition looks the same. At the start I would have assumed everybody's objectives were the same as mine, and they're really not. We are all very different, and I wouldn't presume to tell people now. I'll probably just write an article about it at some point, without the lecturing that would have come earlier in my transition, when I was a bit more forceful about how it should be done. Besides, the trans women who have asked for my advice have all ignored it anyway, so there's not a lot of point in giving it. The article format suits me better, to be honest.

Monika: And finally, what's next for Stevie? What dreams and goals are you working toward now?

Stevie: I'll give you the practical answer first, and then the dreams.
Monika: Let's start with the career side, then. Where does that leave you?

Stevie: Practically, for my career, I'm absolutely terrified at the moment. I've been building this huge artificial intelligence factory, and it is so powerful, so fast at building software, that it frightens me. It rather puts me out of work, and it won't be long before other companies build things like it and the very nature of my work changes. So I'm in a period of flux, trying to work out how the hell to monetise my life. My feeling is that I'll end up making money from the services the machine produces, rather than from software consulting directly, or from consulting on how to implement systems like this. Time will tell 

"I'm looking to build
a brand called Become."

What I do know is that I'll keep trying hard to be excellent, and I'll keep learning. I have never once gone stale on learning. There have been three periods of my life where I fell in love with a technology and became an expert. The first was the internet, back in the nineties. The second was crypto, which effectively paid for my transition. The third has been agentic AI. All three gave me the life I have today, so I will continue.
Monika: And on a more personal note, is there room in your life for someone else these days?

Stevie: On a personal level, I'm not really keen to jump into sharing my washing machine with somebody else's socks any time soon. Although I would love somebody special, somebody who can spar with me.
And then there's the thing I feel most strongly about. I'm looking to build a brand called Become. It exists because I got tired of a world where services for transgender women are either an afterthought or a compromise, where everything we're offered arrives with an asterisk. I want to build grade-A services, designed for us from the first line, with no asterisk. If in ten years a trans woman anywhere in these islands can say, it's a Become service, so it'll be done properly, that's the whole ambition. Grade A as standard, for people who have been told for too long to be grateful for grade C.
Monika: Beyond Become, what else is on your plate?

Stevie: I'm also looking at building a business around university lecture capture, which is drier and more boring, but there's a good market for it and I know that world well. I'll keep writing Fast Track Femme. And I'll be working to rebuild myself financially from the catastrophic losses I suffered trading a few years ago.
As for surgeries, I'm pretty much done. Although I am considering rib surgery, and lots of people tell me off about that and say I shouldn't. I've never been one to listen.
Monika: And the dream itself, the one behind all of this?

Stevie: And the dream? I want to be an inspirational transgender person for other people. I know that sounds vain and arrogant, but I enjoy that role. I want us to be seen in the world as capable people. As I wrote in an essay recently, I want us to look like everybody else, but not in that beige way. We can be successful and crazy and driven, and everything, and proud. We are not victims. That's what I want Become to look like. And I suppose it's what I want me to look like too.

 

END OF PART 3

Back to PART 1

 

All photos: courtesy of Stevie Bennett.

© 2026 - Monika Kowalska