Interview with Stevie Bennett

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.

 

Monika: Stevie, welcome to The Heroines of My Life! Thank you so much for accepting my invitation and taking the time to share your story with my readers. I'm really happy to have you here. How are you feeling about being on the other side of the interview for a change?

Stevie: Slightly nervous, which is ridiculous for a woman who publishes essays about her own divorce, surgery and hormone levels for anyone with an internet connection to read. But writing about yourself is one thing. Answering someone else's questions is another. You lose control of the framing. So thank you for having me, Monika. I went down the rabbit hole of your archive for an entire evening, and it is quite something.

Monika: I have to admit, I am amazed by people who do Ironman. The thought of swimming, cycling and running such long distances in one event is completely beyond me! What made you take up a sport that demands so much time, discipline and physical endurance?

Stevie: The truthful answer starts long before the bike. I spent my twenties absolutely wedged in gender dysphoria, a complete mess, an absolute disaster for a human being. Drugs, cross-dressing and computer programming were my life. And it was strange, because I had two obsessions running at the same time: software engineering, and trying to become a woman. At one point I had to make a choice. It was a long, long time ago now, and I chose to try and be a man. 

 

"I spent my twenties absolutely wedged
in gender dysphoria."

Monika: What did that choice cost you?

Stevie: The price was awful. I put on a lot of weight. I looked awful. And then I developed this weird obsession with my body, but not like the looks-maxing kids are obsessed with theirs. I didn't care how it looked. I was obsessed with metrics and stats, with what I could make it do. And if you're going to end up obsessed with metrics and stats about what your body can do, all roads lead to Ironman.
I was an appalling swimmer, a good cyclist and an average runner, which at Ironman distance makes you an average everything at best. Enter the London marathon and you can look around and spot the amateurs, the ones doing it for fun. Nobody enters a full Ironman for fun. Everyone on that start line means business and has spent a year and a half training, at least. There is nobody on that start line who is the rank amateur, the poor candidate. It's probably you.

Monika: I'm fascinated by what happens when you're deep into an Ironman and your muscles and body are screaming that they've had enough. Is there a point where your brain somehow switches off or changes the way you perceive the pain, allowing you to keep going when physically you feel you should stop?

Stevie: I could give you the stock answer, the cliché about the mind eradicating the pain and all that. The truth is more ordinary. I did a lot of events, mainly long-distance cycling, and I was good when things were going well. But when things started to slip, when I wasn't making the times I wanted or the power numbers weren't where they should be, I have to admit I struggled. Sometimes I gave in a little bit and just got through. I think that's everyone's battle with these things. It is so mental, over physical.
And the truth is, I overtrained. I wasn't young even then. I was in my forties, and I was generally better trained a month before an event than by the time I got to it. What carried me through wasn't willpower. I was Steven David Bennett, the Ironman of East Dulwich, the one people saw out training on the ridiculous fancy time trial bike, the one people endlessly asked, how's it going? I couldn't fail because of that. In some ways I used it as motivation. In some ways it was pressure. By race day my back was so screwed I could barely walk, and I did it anyway. I'm a little bit proud of that, and still embarrassed that I wasn't very good.

Monika: You spent years running enormous distances, but looking back, it seems you were also running for a very long time from yourself. Do you ever find it ironic that Stevie, who could finally run an Ironman, was, for decades, also running away from becoming herself?

Stevie: Throughout that entire period of my life, from my late twenties right up to when I finally transitioned, I ran it as a series of bargains. If I just do this, I will be content. If I just do that, I will be content. That is not to say that having a wife and a family didn't make me content. It did. It just wasn't complete. And sport was the same, and money was the same. If I just make this amount, I'll be content. If I just get good enough at this, I'll be content. I was constantly chasing something. That seems so apparent to me now, but I couldn't see it back then at all. Always the next thing.
So was I running from myself? I suppose I was. I just called it ambition. 

 

"So was I running from myself?
I suppose I was."

 

Monika: Do you remember the first time you encountered another transgender woman in real life and thought that perhaps she was showing you something about yourself?

Stevie: I'll be honest, the first transgender person I ever saw wasn't in the flesh. It was Julia Grant, on TV in the UK, back in about 1979. There was a whole documentary series about her, A Change of Sex, I think it was called. I found it really hard to watch, because I sort of knew what I was already by that stage. I'd been dressing as a girl privately since I was five. I always knew it.
And I'll be very honest about the real-life half of the question too. The first time I saw a transgender person in the flesh, I think I felt really uneasy. She didn't pass well, and I remember thinking, I could never be that brave, I just can't do it, I'm just going to have to get on with it somehow, aren't I? But yes, I was fascinated by Julia Grant.

Monika: You met your future wife in Dublin when you were thirty-six. What was the attraction between you like, and what did you see in each other at that time?

Stevie: I'll be honest, that's a tricky question, because I'm always very careful not to invade her privacy, and I only ever talk about her in the abstract. But I have nothing but good things to say about my ex-wife. She is an immense human being. She has her blind sides, but they are made up for a thousand times over by her strength. She is an incredible mother, and one of the most capable people you will ever meet. If she has a thousand things to do and you give her another one, it will be done. She has qualities I do not possess. I am great at hyperfocus, but I am appalling at remembering to pay the gas bill.
Monika: What did the two of you have together, at your best?

Stevie: What I remember loving, at the peak of us, was how we communicated. We could play together with a level of metacognition that would probably baffle an outside observer watching it in full flow. We could sit on a Saturday morning chatting playfully away for hours. I genuinely miss that, deeply.
Things turned very sour with us at the end, and they have never really improved. I'm not going to dress it up. In some ways I destroyed her life, and we'll live with that forever. In the end it was a circle that could not be squared. I was this. She felt betrayed, and she was not attracted to this. I have to accept that.

Monika: You went on to marry, raise three children and build a family life together. Did having a wife and children make it easier to keep your transgender identity buried, because you had so many other roles to concentrate on?

Stevie: There are probably two reasons I didn't transition younger, and I'm going to be very honest about both. The first is that I'm quite vain. I didn't want to look bad. I didn't want to not be attractive, and I just didn't think there was any chance I could ever look okay. The second is that I really loved my wife, and I still love my children, and they were the reason I didn't transition. I held that role for many years.
But I felt myself slowly diminishing and shrinking inside it. In the end, I hardly knew anybody. Steve locked himself away in his office and just worked all day. He didn't communicate much with people. He got angry with the world.
Monika: So what finally changed for you?

Stevie: What changed it for me was starting to realise that maybe it could work. Maybe I could look okay, make a success of it, and people would still hire me. And for that I have to thank five or six women I saw on Reddit at the time, women in their late forties and early fifties who had transitioned late, some with backgrounds quite like mine, and who had made a real success of it. Some of them have since disappeared into complete stealth, by the way. They did it that well. And I can respect that. But that was what swung it for me: realising that maybe, just maybe, I could look okay.

Monika: You have written with great honesty about loving your wife while also knowing that something fundamental about yourself remained hidden. Do you think it is possible to have been genuinely happy in that life and still have been deeply unhappy with yourself?

Stevie: It is entirely possible. I was very happy with the people around me, and very unhappy with me, and with my manifestation in that life. That's the line I would draw. I could never be happy with me, but I could be happy with them. And I'll be honest, the version of me they were getting was, over the years, getting worse. 

 

"I was very happy with the people around me,
and very unhappy with me."

 

Monika: Your family eventually lived in rural Ireland. Looking back, when did you first realise that the life you had built was no longer sustainable in the form it had taken?

Stevie: I'm not going to give people specific dates for when I started transitioning, because I don't like doing that. But the true answer to your question is medical more than anything else. The barriers came down, and my brain just couldn't keep it all at bay any more. After a lifetime of holding it, the holding simply stopped being possible. That's the real answer, and I suspect your next question is about to make me explain it properly.

Monika: You have written about developing Graves' disease, a serious condition affecting the thyroid, during the period when your body was also beginning to feminise. For someone like me who knows very little about Graves' disease, could you explain what happened to you, how it affected you physically and emotionally, and how this unexpected health crisis became connected with your decision to transition?

Stevie: My experience is probably unlike anybody else's. I've certainly never heard of another one like it. To understand it, you need three pieces.
First, I had always had pretty low testosterone. Second, I had issues with excess aromatase, even though I was not overweight. For those who don't know, aromatase is the thing that flips your testosterone into estrogen. All men have some of it, you need it, I just seemed to have too much of it. I suspect that's probably what gave me issues with gynecomastia, wider hips than average for a man, and small hands, among other things. I don't know, I'm speculating.
And then the third thing in the trilogy was Graves' disease. It's an autoimmune disorder, and while it can't be stated definitively, it's generally stress-induced, or can be. I developed it not long after some catastrophic losses in trading. I won't go into the numbers, but they were life-changingly bad, and I had never felt so stressed in my life.

 

END OF PART 1

PART 2

 

All photos: courtesy of Stevie Bennett.

© 2026 - Monika Kowalska