I am proud to share that today, June 19th, marks the first day of my social transition. What once seemed impossible - a distant, shimmering mirage -has finally become my reality. At 49 years old, I am officially beginning my life as the woman I have always been.

Surprisingly, this piece isn’t really about me. It’s about everyone else.

We are told constantly that the current political and social climate is “anti-trans.” There is, sadly, no shortage of evidence regarding the cruelty and dehumanization directed at our community. But as many have observed, this vitriol is often driven by a loud, radical minority. Much has been written on their tactics, and it is not my intention to give them more oxygen here.

Instead, I want to talk about the humans I actually interact with. The family, the friends, the colleagues, and the strangers in gyms and coffee shops. I want to talk about the “Tidal Wave of Support” that met me when I finally stepped into the light.

The Power of Allies
Before I continue, I must acknowledge my privilege. I have had a “lucky” path. My heart breaks for every transgender person who has faced rejection, violence, or oppression. I do not write this to diminish those very real struggles; I write this to offer a roadmap of hope and to celebrate the allies who make life livable.

My most consistent champions have been my daughters. They have taught me strength and courage through their own lived experiences. They are amazing young women who live their values with fierce conviction. I could not have reached this milestone without them. Who knew that being a “very imperfect parent” would result in such a perfect support system?

I have also found a new “chosen family.” Among a beautiful circle of cis and trans friends, I found a transgender sister. We are like twins in every way that matters - even born less than 24 hours apart. She has been one of the greatest and most unexpected gifts of this journey.

Safety in the Boardroom
Perhaps the most surprising support has come from the wider circles of my professional life. I am a senior executive at a small, VC-backed company. In that world, the pressure to avoid “distraction” or “risk” is constant. It would have been easy for my leadership team to quietly dissuade me.

Instead, my colleagues have been steadfast. Not once has anyone questioned my decision or treated me as “less than.” They value what I bring to the table as a professional, and they have made it clear that my gender does not change my value. My team views my ability to transition safely as a reflection of the healthy, inclusive culture they’ve worked hard to build.

The Quiet Moments of Grace
Then there are the people who help us rebuild ourselves in the small, quiet moments of the day.

A year ago, I started working with my PT, Mark, to reverse years of sedentary living and “numbing out” with alcohol. Mark is a natural observer of the human condition. When I told him I was transgender, he didn’t blink.

He simply said: “Great. When you’re ready to transition at the gym, tell me. I’ll be there with you for your first session.”

At the time, I was still struggling with my weight and living in a very dark place. He will never fully know how much that simple promise of protection meant to me.

More recently, I found an unexpected ally in Sarah, who makes my coffee every morning. Our office is on a science park with an excellent cafe, and when I first opened up to her, I had no idea how powerful her support would be.

I’ve come to realize that the most impactful things are often the smallest. Every day since I shared my news, Sarah has greeted me with a specific kind of warmth and affirmation. She made me realize I could begin expressing myself differently even before my “official” transition date. Visiting her has become my daily guilty pleasure; she pours so much joy into my emerging story that I often find myself forgetting the fear I carried for so long. (And she makes a truly amazing Americano.)

Finally, there is Ellie. For those who know the grueling “joy” of electrolysis, Ellie is the calm in the storm. She makes two-hour sessions of discomfort endurable. Six months ago, I finally found the nerve to show her a photograph of my authentic self.

She looked me in the eye and said she didn’t understand why I hadn’t transitioned already.

I had a thousand logical reasons ready - excuses I’d been rehearsing for decades. But in the warmth of her gaze, they suddenly didn’t matter. Her comment unleashed a wave of euphoria I can’t begin to describe. It was the final permission I needed to stop waiting.

The Reality of Transition
Today, I step out as myself. The world can be a loud, scary place, but my “real world” - the people who see me, work with me, and love me - is filled with grace.

To the allies who didn’t blink: Thank you. You saved my life.

I have had a sense of femininity since age 3 or 4 that has stayed with me my whole life. Often I have buried this part of myself, hidden it in boxes and tried to pretend it was just a random thought (or equally absurd, everyone thinks like this). She was always in my dreams. Very intensely in my teens and 20s. And again in recent years. It breaks my heart that in my earlier life she was mute. Her voice was never permitted in my dreams let alone considered in my day to day reality. She was just there, with sad eyes and at times, a look that sat in between pain and hope.

Approaching the 50 year milestone, I find myself actively embracing a choice I never felt that I could make. Over three years into HRT and with close to 100 hours of therapy under my belt, I am committed to choosing the real me, not the shadow I was told to be. This has been harder than I care to admit. Other life events didn’t stop simply because I started questioning my gender. And that questioning, even before I reached a decision has had consequences. My second marriage is now fully adrift and we will separate as good friends. This has been the biggest single pain point for both of us and I am grateful to my wife for her courage in not taking any of the easy options. Without her, I would not be here. In parallel, I continue to put tremendous energy into my parental role, struggling at times to help my children overcome the challenges that modern life throws at them. My children have been wonderful supporters of my journey and continue to teach me that I overthink things. Their love has been key to me leaning into this next chapter and I would have struggled to move forward as I have without their blessing. I am lucky to have found a small band of friends who get me, and I them. I’ve never experienced that before (not without masking and people pleasing) and there isn’t a day that goes by that I don’t connect with at least one of them. I have made some of my own hard yards along the way. Weight loss has come through steady work on my diet and at the gym; I find myself loving my body for the first time in my life! My feminization road map continues to evolve with hair removal, voice lessons and a feminine capsule wardrobe which now exceeds my masculine wardrobe. And make up and self care are now sources of joy rather than a dreaded task!

Before 2026, I could not have believed that my journey would look like this, specifically that I would have the courage and means to choose being a woman of transgender experience full time. My plan is to make the the full time transition in October this year, which gives me time to sort out some of the administrative and medical challenges. I now have adopt my female name increasingly with my online shopping and have started to plan for moving different accounts including bills, bank accounts and identity documents “across” to my new identity. I have engaged with my work and they have been warm and supportive. At this stage all of the major people in my life know and it is a matter of counting down until October!
The dysphoria is still there but my relationship with it has changed. It is more of a “dissonant north star” than a monster these days. Accepting that my dysphoria is part of me being transgender has given me a more balanced outlook on life. It is not something to hide from or be afraid of. I sit with it and learn from it. As a result, validation is something I do increasingly for myself, rather than through others, a necessary life lesson I’d been avoiding for over 40 years. Having spent the longest time wishing I could achieve “stealth status” and pass as a cis-woman, I have moved on. I am a proud transgender woman and I will not apologize to anyone for that. I look forward to wearing my identity with pride and finding the joy in all the little things! This is my reality now; it’s no longer a dream.

I started to crack my egg just before the world went sideways. I have been on HRT for almost 2 years now with a higher dose over the last 9 months including GnRH agonist injections, supplemented with a high dose of progesterone in the last six months. I have embraced all of the HRT induced changes, the most recent and pronounced being my breast development. Just shy of 49 years old, I am grateful to have a strong and very natural B cup. The most important changes have been to my emotional processing and to my skin.

During my HRT journey I have watched the world turn against transgender people. Blind hatred, ignorance and increasingly hostile legal positions both in the UK and US have really challenged many of us. And to my surprise, as a conformist, I have not stopped my journey. Up until now I’ve been in a relative degree of stealth with family, close friends and my employer aware but still presenting as something between male and androgynous. For the longest time I daren’t have believed that I could further.

So what changed? If we start with the short version, reality hit. And at times it really “HIT”. As a parent, remarried and with a fairly senior role in my industry which involves transatlantic travel, the path forward was always going to be fraught. Lots of excuses to blame everyone else and just hide. But the most important people to me in my life, my wife and my kids have stepped up. Before you think it’s happily ever after in the style of Hollywood, I need to quash that idea. In making this journey with my wife, I am losing my marriage but regaining my best friend. It’s bittersweet but in so many ways it is the right path. Independent of me and based on her own experiences of the last decade, she has realised that her personal space is important to her. Adding my transition is just too much and is not the right romantic fit. I respect that deeply. That said, she is (and has been) my greatest champion. Even in moments when I wavered.

This weekend is extra special…having briefed both her sibling and her Mum previously, she told the rest of her family. They want the best for both of us and I’m humbled by their love and acceptance of this development. They are part of my chosen family.

So what does the future hold? I will be honest and say much of it is opaque. But I see me evolving my career to be less investor/customer facing, more authentically me and living near my best friend while also holding space for my kids as they move through their mid to late teens. I believe social transition is 18–24 months away and part of that will involved surgery. I support everyone’s’ expression of gender; just in my case I lean to a more binary expression of myself. I am grateful for this space and to be able to share with you all. Thank you x

For me it is something I’ve hidden from for most of my life and only recently tried to understand if you’ve read any of my writings on Medium. Put a different way, I’ve tried to find every reason I could not to be trans, to explain it a different way or when all else fails, to suppress myself and who I am.

I am done with that!

So here I am…a partially cracked egg and not fully out. I thought it would always be about the big reveal…telling people I’m “me” and that I don’t fit the gender binary. Naively I believed that was it. All of it. I was so wrong. At my age it is hard to suddenly change the fundamental assumptions of…well…everything. The platform wasn’t designed for it! Let me put it another way, my feminine sense of me is resplendent in every sense of the word. She is not letting me pick a date in a my first decade and saying “let’s start here”.

It is devastating to realise how much I have missed about myself and the memories I’ve not created either as a masculine or feminine person. Because therein lies the truth. You can’t fully be what you think you are if you can’t reconcile yourself with the things most important to you. My feminine sense of me lacks a range of experiences inherent to who I feel I am. Some aspects are out of range…I will never be pregnant for a start. Ever!

I “skipped” past what should have been key moments in my life.

But honestly the greater challenge is temporal. I “skipped” past what should have been key moments in my life. As I undergo a second puberty (I’m tentatively two years into this), my experience is compressed. Both temporally and in terms of perceptive. The two things overlap but they are not the same, not even close. What I can tell you is that in each decade that I live beyond the age of four, I felt lost, confused and genuinely unable to fit correctly in the world. And now that I feel it makes sense, the world has passed me by. No amount of giving up “white male privilege” seems to matter in the eyes of the world. And in my eyes, I can’t get back what I missed.

I admire the younger generations of trans-folk as they figure this out better than I did. And I don’t want that to sound like cheap praise. I think there are more tools to support transgender people now than ever existed previously but anyone who takes this path now is facing an enemy who perhaps has greater resource and motivation to crush what we are. It is never the easy choice.

The hormones make me a better version of me.

So where does that leave me? Well for a start, therapy is a life line that stops me sliding off the edge of the world (ps. the world is not flat in spite of what of MAGA thinks). The hormones make me a better version of me. I am at peace with my emotions and my physical sense of self continues to evolve positively. I cannot lie, there is a toll on those I love. Lying to them about who I am would be worse in my view but I’m sure there are anti-trans activists all over who would happily counsel me differently.

Please forgive me.

Each time I relax my grip on heteronormativity, each time I share my sense of me with another person, I become more me. And more likely to transition. It brings me joy and scares me in equal measure. I wasn’t given a choice on this. It’s who I am. Please forgive me.

My biggest support comes from my wife and my eldest daughter. I have told close friends but it has been harder to connect with them on this than I thought. None of them are trans or queer. Responses range from warm and generally helpful to slightly awkward and misguided but always with good intent. They all want to help but none of them seem to know what to do. And I don’t know what to ask for!

This has made me realise that I need to move in some new circles with people who are on the same or similar journeys. Which perhaps hides my greatest learning…there is no approval that I can receive from any group of people that is going to make this easy. As an introvert and someone with ADHD, I find this all very challenging. So many signals, no small amount of vigilance and a constant fear of rejection.

I wish I could wake up somewhere new and just be. It’s not a great thought process and I’m aware of that. It does reflect my ongoing sense of stalemate. I am lucky enough to be able to secure hormones in the UK through a private prescription. I recently added progesterone to my regimen which seems to help my ability to sleep. I did taper my oestrogen down somewhat. Mood wise I swing between wanting to take a higher dose of both hormones and then wanting to be cautious. In spite of not taking blockers, I am already at the very lowest edge of the normal male level for testosterone.

So as I’ve drafted this article over a number of weeks, reflected and continued to engage with people, things have happened. I will start with the punchline…I feel a new sense of joy! My body has continued to evolve and I have rediscovered my sense of momentum, working on being healthier and making my peace with my self image. I have told some other friends and former colleagues, not least of all the parents of my god child. They have all been lovely beyond words. At this point I’ve told enough people without a negative reaction that I need to embrace that for what it is. I know many of my fellow trans travellers do not gain acceptance of any sort when trying to come out. To be clear I am still presenting male a lot of the time but with a softer look and people now realise my skin is so different due to oestrogen (not a chemical peel, sunshine or any other number of suggestions I’ve received).

I’ve kept the best to last. My wife and I have had the biggest of big discussions. Possibly the most vulnerable discussion we’ve ever shared. Our marriage is evolving. We’re both neurodivergent and I am obviously trying to figure out being trans. We have a design for our future which keeps with both our values. It is authentic and fits with our shared values. Many of the details are not yet clear, even to us but we are committed to facing what life throws at us as a team while also unconditionally supporting each other in the next chapter of our story. I wince reading the words…they don’t do this justice. Hopefully as I tell my story more, I will find the right way to share. For now I will just say that my wife is my best friend, greatest ally and soul mate. She has taught me that it is okay to be me.

I developed a sense of the forbidden. Certain sound sounds, some lyrics and how people presented in the world of music made me feel deeply uncomfortable. I hid from this. How could men wear long hair and tight leather trousers? Make up and cross gender outfits was a challenge. I remember seeing Bono as MacPhisto and I felt so strong feelings that made me uncomfortable and unable to process the performance. His effeminate clothing, the sensual overtures and platform heels were trying to speak to me and I was doing my best not to listen.

And yet there was something burning inside me. After leaving school and having a year out and away from the people I had known, I relaxed a little. Outwardly conforming, wearing levi’s jeans, boots and a leather jacket. Scowling at the world. This hid my love of Alanis Morisette and Jagged Little Pill. Those lyrics spoke to me and I didn’t understand why. I craved to have the right to be what she sang about. The femininity, being craved, not masculine. Being understood.

_You’re the best listener I’ve ever met. Best friend. Best friend with benefits_

Not all of it was aspirational femininity. My relationship with my parents, especially my mum was complex. She set expectations for me that were sky high, ambitious, traditional and very cis-hetero-normative. Trying to redeem herself by shaping me into a man.

> Be a good girl. You gotta try a little harder. That simply wasn’t good enough. To make us proud. I’ll live through you. I’ll make you what I never was

How ironic that the lyric named how I felt inside that I couldn’t tell myself. A good girl…or at least trying to be.

Garbage was another guilty pleasure. Shirley Manson some how personified what I couldn’t express outwardly. I felt alien, not see and without a place in the world. Stupid Girl was an anthem for me through and through. Is it too much to admit I loved Bleed Like Me?

> I am weak. But I am strong. I can use my tears to bring you home

And the prescient Queer. It made me burn every time I listened to it.

> Hey boy, take a look at me

> Let me dirty up your mind

> I’ll strip away your hard veneer

> And see what I can find

It was like Shirley knew my secret that even I couldn’t name at that time. So frustrating and painful. Trapped on the very edge of my own sense of self and not able to do anything about it.

> You choke behind the smile. A fake behind the fear. The queerest of the queer

And still I maintained the illusion. People pleaser. Over ambitious and squeaky clean. Terrified to be seen. Masking for all I was worth.

At university it should have been easier. The late nineties were a good time to be a 20 something (YMMV). And somehow I built a life that allowed me to be anything but me. Unable to express myself sexually or through my gender. It took me months to buy George Michael’s older. I was convinced that everyone would know in an instant that I was living a lie. I admired him as an icon and that album spoke to me. Jesus to a Child felt like confession. God could accept me for what I was becoming even if I couldn’t.

> Kindness in your eyes

> I guess you heard me cry

> You smiled at me like Jesus to a child

> I’m blessed

And then to Fast Love. A hint of the. redemption that I would never realise until much later in life. Seeking affirmation and some fun.

So here I am, approaching fifty and still figuring it out. I have new artists I love with tracks that speak to me. My daughters keep me current with Billie Eilish and Doja Cat. Maybe this is my second chance.

I have always known I felt different, ever since early childhood – probably from around 3 years of age. Hiding from these feelings and not sharing them with anyone allowed me to cope, masking as a typically cis male well into my forties. I cannot fully rationalise what gave me the impetus to change things but it could not have happened without my wife who is simply amazing.

My HRT journey began 16 months ago with a private prescription. The decision to undergo HRT was a big one for me and I am lucky to be supported by my wife on this journey. I started with a relatively low dose which has been increased several times during this period to what most would consider a modest dose at best. Each morning and night I maintain the ritual application of hormone gel to the muscles of my upper legs.

The changes that I noticed most during the first half of my HRT were subtle. My skin is more sensitive to touch and to cold. I find emotional regulation is more natural for me, although I am never sure if this is a direct effect of the oestrogen or that simply I am happier being me because I am on HRT. My face has softened, amplified by the loss of my beard and the intensive laser hair removal. For the first time in my life I actually like my face; it was never that masculine to begin with and always felt terribly “in between”. I feared being read as “not male enough” when I was growing up. Now my face has a softness that reflects my nature and the texture of my skin is often complimented by colleagues who assume I’ve had a chemical peel or have started moisturising.

In recent months, the development of feminine breasts has moved up a gear. Several gears in fact. They are more pronounced and can be eager to be seen in much of my clothing. Initially I was aware of a growing softness in my chest tissue and lord knows I had a keen awareness of anything touching my nipples. But now there is a consistent swelling and change of shape which even my crop tops which I wear under my shirts cannot mask beyond a cursory glance. And while affirmation washes over me and I appreciate how wonderful my body is, it creates a problem for me; I don’t have a plan for transition and I don’t feel I can turn everyone else’s lives upside down without good reason.

Normally when I am facing pressure or uncertainty in life, I double down and try hard. I learnt from a young age to be competitive albeit sometimes being recognised more on the basis of participation was the limit of what I achieved. Sports were something I learned to enjoy but was never naturally gifted at unlike my younger brother. Academically I always did well and this has given me a good career. And this makes my current situation that much harder for me to process. For the first time in my life on something that matters, I feel the need to back off and accept adversity. I will reduce my HRT dosing to a much lower level to significantly slow or stop my breast development while. I figure out what my path really looks like.

In my darker moments this feels like giving in or selling out. And I can be very mean to myself about this. In calmer moments, I reflect more. I know that I am not more or less feminine based on my chest size. Femininity is an innate quality that I have, not simply the physical expression or the performance. And yet my competitive side finds it hard to accept that as an explanation.

I admire so many of the other transgender writers on Medium. Their courage in finding their path is a source of inspiration for me. I know that the path is winding to varying degrees for all of us and this one moment does not define me in the long term. If only transition and transformation was as easy as it is in my dreams!

15 months into hormone replacement therapy and with a supportive spouse, I thought it would all start to make sense and I would grow fully into my feminine identity. I have had nights out with the girls – a mix of trans and cis gender female friends. I’ve told a handful of friends and close colleagues. I am registered on the never ending waiting list for the Gender Identity Clinic in London.

So what is missing? Why do I feel stuck?

I will go straight to the punch line; I honestly don’t know what is holding me back. I would like to say that it is all society’s fault and the growing backlash against transgender folk, especially those who are assigned male at birth is totally to blame. But in good faith I cannot write here and make that claim. I have a relatively privileged life and I see others in the same societal conditions who have less and are oppressed more living their truth.

Internalised misogyny/transphobia is another consideration for me. It has taken me over 2 years of reading and speaking with people to educate myself about identity politics and gender ideology. I have come a long way but I know that my work on this is not (will never?) be complete.

You are probably picking up my energy as you read this. I clearly don’t believe I am trans enough to identify as me. I ask myself why and come back to the same themes. The narrative in my mind is not particularly healthy and demands the impossible. I feel I have to accept I’ve lived a lie for the majority of my life and in doing so I have misled people and should I choose my gender identity over everything else, it means I’m selfish and open to hurting those I love. This is the voice in my head, not my cognitive opinion. This voice keeps the most hurtful assertion until the end. I am not authentic as a transgender person, I’m just performing gender.

This voice in my head has created the perfect mouse trap, one that is both invisible yet securely limits my sense of feminine aspiration. I re-read this and it does not sit write with me. It smells of learned helplessness. The mouse trap is a metaphor for my own self sabotage which only I can change. The power is in me, should I wish to embrace it.

For now, it’s back to the drawing board.