Musings of a Singaporean Transgender

(Spilling the beans, after so many years)

I finally came out to my parents on 18 April 2025, Good Friday. No special significance other than wanting to give them more time to digest the news over the long weekend, although I had been joking with my friends that maybe my Mum would be extra understanding during the holy days where Jesus died for our sins.

Coming out to my parents was a key step in my transition journey, because I felt they had to know before I started telling more people about myself. The last thing I wanted was for them to hear from another source that their son is Transgender. Being a person who likes to be in control instead of leaving things to fate, telling them first was my way of de-risking a potentially incendiary situation. I had been wanting to tell them since February, but due to house moving, a super hectic Chinese New Year, followed by a family holiday in Japan, the wife was very uncomfortable with the timing. In addition, she felt that I didn't have a confident answer regarding how we will deal with our kid, which was something that my parents were bound to ask about. As a result, I postponed coming out, but it weighed increasingly heavily on my chest. After multiple rounds of back and forth, we finally came up with a detailed FAQ on how to address the tougher questions.

I had many fears about how they would react to me being Transgender. My Mum was a staunchly devout Catholic, so there was a chance of rejecting me and what I was doing to my body (i.e. taking hormones, thinking of surgery). As for my Dad, while he had a more YOLO, pursue what you want in live mentality, he is an Asian Dad and I was the eldest (and only) son in the family. How they would react was a dice roll.

I had been rehearsing coming out to my parents during the drive to work, arranging my points for cohesiveness, making sure they made sense, readjusting the points when it seemed a bit odd. It wasn't easy but I felt ready.

I went to my parents' place for dinner and had some random chit chat with them to try and relax. But I could feel the lump in my throat each time I tried to say that there was something important I needed to tell them. I could feel the fear building and nearly backed out, but it didn't feel right. I knew I would be kicking myself if I didn't see it through today. So I asked my parents if we could adjourn to their bedroom as I had something to tell them. Because I have never requested for a conversation in that manner, it was obvious my parents knew something was up. I could taste the anxiety in the air, especially from my Dad. I knew I couldn't drag it out or the anticipation would just build.

So I sat them both down and started.

I said that what I was about to tell them is very shocking, so I hoped that they would remain calm and allow me to finish explaining before asking questions. That regardless of how they react, I would love them. I told them that I am Transgender, that I have had feelings of wanting to be a girl since I was 5 years old and gave examples. I told them that I am on HRT and was seeing a psychiatrist in NUH, who had diagnosed me with gender dysphoria. I stressed that I was born this way and it wasn't due to upbringing, nor was it their fault. I reassured them that I will not wear a dress in front of my kid until she is a teenager and understood things better (this however, is something that I don't agree with, but to quell potential anxieties, that was the stance I took). To make things easier, I wouldn't wear a dress at family gatherings too.

Despite multiple rounds of practice, the words that came out of me felt like a gibberish mess in comparison, slow and stuttered with me constantly looking away, only stealing the occasional glance at their faces. I could see that my parents were trying their best to stay calm and understand the situation. They asked if there were medicines that I could take to managed this "condition", to which I explained that there was no such medicine. The solution to gender dysphoria in my case was to start HRT and transition to live as a woman.

My parents' concerns were primarily about bringing my kid up well and my wife's views on me transitioning. My Mum said she would pray for me, while my Dad (who has a more enlightened view to life) said that the most important thing is that I live my life and pursue happiness, but don't do stupid things like off myself, especially since I have a responsibility to raise my kid. Everyone else's viewpoints don't matter.

At the end of our chat, my parents reiterated that they will support and love me. It's about as good a reaction as one could expect, although it was clear my parents didn't fully understood what it all meant. But I guess when you've never seen your eldest son in such pain, crying a bit and trying to share heavy stuff, they probably held back their reactions.

Coming out to my parents was terrifying and cathartic at the same time. The huge weight I had been feeling was lifted and I could breathe a bit lighter. They now had answers to why I was growing out my hair and I could come properly spill the beans to more people. Since coming out to my parents, I have told three more close friends, who were all incredibly shocked by ultimately supportive. I feel seen as a complete person, with more people knowing about Isabelle. The imagined scene of my own wake that used to bring me to tears consistently no longer had the same power it does.

I separately approached my parents 2 months after coming out to ask them about insights they have had since I told them I was Transgender. My Mum told me she wants her son and that she will pray to God to help me overcome my mental struggles, to which I responded that I could not give her what she wants. My Dad still maintained his YOLO stance about life, but reiterated the responsibility I had to my wife and child. Hilariously, he also said to ignore what my Mum wants, since it is ultimately my life. It is still early days and my parents will be tested further as I gradually present more female. But it is my life and I am feeling hopeful.

It's amazing that I've already been on HRT for 2 years now. The egg crack, first coming out to my wife, feeling the initial bodily changes due to HRT, feels like a fevered dream. And what a rollercoaster ride it has been the past years. I don't think my life has ever been this tumultuous.

Bodily changes wise, it feels like everything has stalled after the first year. While my hips and bum do feel fuller, I've had fat redistributed to my lower waist that seems to cancel each other out with regards to getting more feminine proportions. Boobs have been the same size since the 1 year mark (friends and I jokingly call them our xlb 小笼包 boobs), while other more visible changes aren't HRT related; specifically the reduced facial hair due to electrolysis and longer hair on the top of my head, which is taking painstakingly long.

Emotionally, there has been so many ups and downs, it's amazing how I even functioned the past 2 years. It's been no secret that my mental state has been terrible since the 9 month mark of transition, battling fears of falling short of my transition goals, envying feminine transwomen in the community that seemed to cross the threshold so effortlessly, worrying about rejection and hating my reflection that I see in the mirror on a near daily basis. The midway transition phase is known to be the most challenging, when you're neither here nor there, but all that can be done is be patient and wait.

My relationship with the wife has also seen many ups and downs. While she is supportive, my increasingly feminine appearance brought out all manner of fears in her and triggered feelings of grief; the loss of the man she married, being replaced by a familiar person, but yet total stranger named Isabelle. Transition isn't easy for the one transitioning, but it isn't a cake walk for partners either.

Nevertheless, there were many things to be thankful for in the past two years. I made new close friends that I feel could potentially be lifelong friendships. I came out to my sister, a close friend and most recently, my parents (a separate blog post needed for that). I started to see the woman in the mirror as my hair grew out, making me hopeful for the future. A few funny moments when guys second guessed their entry into the toilet was validation that I looked female, even though I was wearing uncle berms. And most importantly, having a partner willing to work through the challenging issues together.

The 3rd year is going to be more exciting as I come out to more people. It is scary, but I look forward to it.

When I came out to my friends, most of them were very shocked as there were zero signs that I was transgender. Probably not a good badge of honor, since it just meant I was too good at suppressing and hiding this part of me to the point where it was unhealthy. I'm quite certain the constant hiding and fear of being discovered shaped the way I lived, my personality, as well as taking a toll on me mentally. But that's a story for another post.

I never knew I was transgender until my egg cracked when I turned 35. While I didn't show/feel the common signs that a person was transgender back then (e.g. hate my body), looking back over the years, it was GLARINGLY obvious that I was transgender when I looked at the hints:

Envied the girls during racial harmony day for being able to wear a qipao
Always selected a female character when playing video games
Wishing/praying during birthdays and to God that I would wake up a girl
Wanting to fill my 6 choices of secondary school with all girls school, so that the administration had no choice but to send me to one of them
Regularly wanting to wear women's clothes
Feeling incredible fear that my desire to wear women's clothes would be discovered
Imagined I was put into a chrysalis like Sarah Kerrigan from Starcraft, except I came out female and beautiful
Wishing I was Jaceyln Tay in the local drama Legend of the 8 immortals
Being super smitted by a newspaper cutting of Catherine Zeta Jones from Zorro and wishing I looked like her
Wishing I could grow out and dye my hair, but didn't because I would be questioned by parents and friends
Wondering how it would feel to have female body parts
Wishing I had female body parts
Always identified with the woman when I watched adult films
Not feeling like I could click with the boisterous and sporty boys
Not identifying with masculine heroes for guys like football players
Being very curious about transwomen performers during a Thailand holiday but pretending to be super uninterested
Wishing I could be a bride because the dress was so damn pretty
Staring at brides (when I attended weddings), imprinting in memory how pretty the gown is so that I could imagine myself in it after the event
If I had superpowers, to be able to stop time so that I could go into shops to try on women's clothing safely
Feeling free and happy when I wore women's clothes
Feeling confident and powerful when I finally saw a well dressed female version of myself in the mirror

Ok some of the points in there is showing my age 😅 But the list is so damn long, it was amazing I didn't realise I was transgender until later in life. It was probably because I learned very early in life that boys are not supposed to like girls' things and it was shameful to want it. And saying it out would lead to derision, disgust, being ostracised and bullied. So it became a secret I guarded obsessively, a secret to be taken to the grave. To be fair to myself, there were barely any resources back then. I did try to find books in the library related to transgender and crossdressing, but found nothing. The early internet had some info on transwomen (transsexuals as they were called then), but it seemed so far fetched and impossible that I didn't even consider it a possibility ("I didn't hate my body, how could I be transgender?").

There is a tinge of envy when I look at younger transwomen who grew up with the large amount of information on the internet that sped up their discovery of themselves. Perhaps my egg would have cracked way earlier and I would have transitioned before puberty, without testosterone shaping my body into what it is now. But such thoughts are unhelpful and poisons the mind. Wishing for the impossible is an exercise in futility. There are many things in my life to be grateful for, even in my seemingly tumultuous journey. Like my kid, one of the greatest joys in my life, who would not be around had I transitioned earlier.

So far I reference Isabelle almost entirely in the third person. "Isabelle", "She", "Her". I've also become so adept at compartmentalising that Isabelle's become somewhat of a narrowly defined character. A well dressed, glammed up woman that makes an occasional appearance to paint the town red.

But I've been finding this very unhelpful in my journey to integrate Isabelle into daily life. And most importantly, Isabelle isn't a separate persona, nor is she just one part of me. I am Isabelle. In entirety, comprising of all facets of myself. The glamorous, dolled-up version, the bare-faced sloppy version, the bespectacled work version, etc. Even moments when I feel masculine or need to play stereotypically masculine roles (e.g. as a dad), these are all parts of Isabelle. I've come to realise that transitioning isn't about becoming Isabelle. It is about accepting that I am Isabelle.

Of course, the reality is that physical changes are important in helping me to see myself as a woman. So a year ago when the reflection in the mirror was very much a short-haired guy, it wasn't possible for me to see myself as a woman. And I've been so used to doing this huge switch from frumpy guy to dolled-up woman, that it has been a challenge to see myself as Isabelle without makeup. But as I reach my 2 year hrt anniversary and my hair is a lot longer, the internal barrier to seeing my daily self as a woman has been lowered. There is a need to shift how I view myself.

There's also internalised shame associated with being transgender that is a barrier to integrating Isabelle into my daily life. It still feels weird to tell others the words "I am Isabelle". Heck, I only told my wife recently (Mar 2025) that the name I chose for myself. That's a really long time, considering that I came out to my wife in 2018 and that I have gender dysphoria. So far, it has been much easier to refer to the female self in the 3rd person. But that might have also led to the wife viewing Isabelle as this person that looks somewhat like me but is a stranger, with demands that she be let out, demands that she be seen and acknowledged. Which is very unhelpful in getting my wife to be comfortable with me as Isabelle. But as a friend rightly pointed out to me: "Isabelle...even you're not comfortable with Isabelle". Being secure in my own identity is the first step in integration.

It isn't easy, especially having lived so many years as a guy and building an entire identity as one. But I try to celebrate the small wins on this transition journey and acknowledge that I am a constant work in progress. Slowly but surely, I will come to see that I am a woman. I am a transwoman. I am Isabelle.

The last time I went out in public properly as Isabelle was in April 2023 for Cosfest at Gardens by the Bay. A month later my egg cracked and I started HRT. Since then I've not been in the proper headspace to go out in public as Isabelle. While I did dress up as Isabelle in a private indoor space, I felt incredibly dysphoric about my appearance when I dressed. Gone was the confident Isabelle, replaced with a terribly brainwormed baby-trans. I hated all photos I took of myself, nitpicking every masculine facial feature. I felt like a fraud; a man in a dress, unpassable even with makeup, let alone with a bareface. I stopped dressing up, partly because I was living with parents and didn't have a safe space to transform into Isabelle, mostly because it was just too painful to see that my best efforts fall short of the passing mark.

I could not see myself as a woman. Fighting inner demons on a near daily basis, I was constantly worried about whether my hair would grow out properly, impatient about the effects of HRT and facial hair removal, constantly anxious that even after waiting for a few years, I would still be unable pass. Never mind the fact that when I went out as Isabelle during my crossdressing days, I was able to try on clothes in women's changing rooms and navigate through a mall without too many quizzical stares. My brain felt a bit broken.

But as my hair grew out slowly, I could occasionally see glimpses of the woman I would become. Though I was still sporting a mullet because my fringe wasn't long enough, I felt that maybe, just maybe, Isabelle was ready to make a reappearance, this time without needing to wear a wig. Coming out to my hairdresser and having her reassure me that my hair could work despite my fringe was the validation I needed. Since renovation of my new home was also recently completed, I decided it was time to stop hiding in my shell, driving myself insane by constantly worrying I wasn't going my own expectations. If I was going to present female 24/7, I needed to get used to weird stares and uncomfortable comments from others. I decided to dress up as Isabelle for my voice therapy session and shopping at Somerset.

On the day I was supposed to go out, there was an unexpected hiccup that nearly derailed my plans, because my kid suddenly complained of pains in both her calves to the point where she didn't want to walk. It was quite worrying so I brought her to see the doctor, who did a check and reassured that it wasn't anything to be too worried about. I enjoyed a McDonald's breakfast with the kiddo before dropping her off with my Mum for the day. It was time to let Isabelle out.

I hadn't put on makeup in almost a year, but it was muscle memory at this stage and came back to me rather easily. An hour later, the familiar, dolled-up version of myself reflected back in the mirror. The flaws were still there, but all in all, I didn't look too shabby. I felt brave enough to go out as Isabelle once again. For the day I had picked out a ribbon-tie sleeveless green maxi dress with a floral design. It was dressy enough for a shopping outing but not too formal for wearing in Singapore.

It was the first time I dressed as Isabelle without a wig and holy hell was it such freedom! I wasn't sweating buckets in Singapore's humidity, there was no wig cap constricting my head like Sun Wu Kong's golden headband and I didn't need to worry about flyaway fringes. It was a good start even before I stepped out of the house.

The first stop was my voice therapy appointment at Alexandra Hospital. I look forward to these sessions because the voice therapist I work with is incredibly encouraging. It is also a safe space for me to practice my female voice (which is still terrible and needs a lot more practice in my opinion). As I peeked through the door of the clinic, the voice therapist stared at me quizically for 5 seconds before bursting out laughing: "Omg Isabelle I couldn't recognise you, I thought it was someone who got lost!". We started chatting, updating each other on the things that transpired over the past 5 months and did a few voice/video recordings. I'm not sure why, but she was convinced that while my pitch wasn't high, my voice worked really well with my feminine appearance and wanted to graduate me from her voice therapy sessions (Nooooooooo!). Fortunately I convinced her to give me one more voice therapy session in June.

I went on to meet friends in Somerset for sushi dinner and shopping. Being dressed as Isabelle made me put in the effort to use my female voice more, which I was able to do so for most of the night 😁 We went to the usual hits; Love Bonito, Mango, Zara, Playdress and Pomelo before grabbing bubble tea to round off the night.

Unlike the early days of my crossdressing journey that were primary filled with excitement and euphoria, there was instead a huge sense of freedom and calm this time. I didn't worry about my wig looking out of place (and therefore fake). I somehow didn't get stares despite the Friday night dinner crowds. I felt like I blended in well; just a regular gal out shopping with her friends.

I could use such feeling of calm and happiness more regularly.

2024 has been a tumultuous year, but despite the ups and downs, I think it has been a net positive overall.

Work has been largely frustrating for the first half of the year, leading me to seek out a more stressful but perhaps more rewarding role. So far it seems promising, so fingers crossed there.

Relationship with my Wife came so very close to the precipice. Fortunately the foundation we built over the years helped to hold it all together. It took a while and many, many tears, but we managed to become more honest with each other and ourselves. While still a work in progress, we are now able to communicate at a level that we have never been able to do before. Home is stable and I am extremely thankful for that.

My mental state has been generally terrible this year, as described in earlier posts. Dissociating happens a lot in order for me to continue functioning. But through the emotional roller coaster ride, the pensive thoughts, I've become a bit more in touch with my emotions. I'm learning how to reach through the layers of bubble wrap to connect with feelings other than rage, impatience and envy. I've broadened my emotional vocabulary that allows me to better describe why I feel a certain way. I'm still working on being less self-critical and learning to love myself despite my flaws.

I still don't see Isabelle in the mirror and get "sir-ed" consistently by random people I meet (which sucks). Granted, my polo-tee and berms look definitely screams "Singaporean Uncle", but it would be nice to see the occasional confused look in people's eyes. Currently I still feel like an imposter and not confident enough to present female without makeup.

My new home is finally taking shape. Renovation delays despite my best efforts meant that I cannot move in by the end of the year, but I'm almost near the finish line. Which means a larger safe space for me to express myself a bit more.

2024 was a hectic year. 2025 is already promising to start off blazing with action. But I am holding to hope. With some time and luck, Isabelle might regain confidence to finally show herself more regularly.

This photo captures how my transition journey feels at times. There is a road forward that many middle-aged transwomen like me have taken, but it is shrouded in misty uncertainty. I don't know how long I need to travel on the road, nor do I know whether there will be obstacles or unexpected forks in the road. It feels like a long, lonely journey, but I know that the only way is forward. Left foot, right foot. Keep moving forward.

I've been on HRT for 1.5 years now and if you've been following my other posts, mental health has been a struggle since February this year (10 month mark onwards). A lot of it stems from anxieties of the future, fear of acceptance by people closest to me and worries that I will not be able to hit the goals that I set for myself despite my best efforts. Seeing a rather guy looking person in the mirror and bodily changes such as hair removal and fat distribution happen at a glacial pace doesn't help either.

I'm in a midway transition phase right now, which is the hardest part of transition. A recent video from Dr Zhikhareva highlighted why the midway transition phase is so damn hard, even more so that the initial decision to begin transitioning. It was a video that resonated with me, but also served as a reminder that better days are to come. I just need to be patient about it and kinder to myself.

Usually when we see photos of transgender individuals online, they're usually happily transitioned and living as their authentic self. A pre-transition photo is also usually shown as comparison to contrast how far they have come. The journey of these transwomen and transmen are something to be celebrated for sure, because it was definitely not an easy one. However, you will be hard pressed to find photos of the midway transition phase. Understandably so, because who wants to show the part of their journey where they feel ugly, incomplete and vulnerable?

It is this middle phase where there is significant uncertainty in what is to come in the days ahead. It is a period where misgendering often happens, because appearance wise we are somewhat in between the binaries. Family, friends and colleagues are also just coming to terms with news that you are transgender. Internally, there is also significant impatience in reaching the end goal of "passing" and living as our intended gender. The difficulties of the midway transition phase can be exacerbated by the lack of financial / social / emotional support. Imagine feeling like you need facial surgery in order to reduce certain masculine features and misgendering, but do not have the financial resources to do everything.

Transitioning is usually likened to the important chrysalis phase, where the fuzzy caterpillar transforms into a beautiful butterfly. Time is needed for the body to change, for the wings to form and harden. It cannot be rushed, otherwise the metamorphosis is incomplete and what emerges is a butterfly that is unable to take flight. Many a cautionary tale has been shared where some transwomen rush through the physical aspects of transition (facial feminization, SRS, body sculpting, breast augmentation), but are still deeply unhappy because the integration and self-acceptance has not been done. However, the chrysalis is a vulnerable phase that sometimes feel like it is in the way of getting to the end state of becoming a butterfly. Also, nobody wants to be a freaking Metapod.

(Like seriously, how do I win battles in life if Harden is the only move I know)

Just to end off the post, I have been making multiple efforts to better my mental health. While I still complain to my friends regularly and go into my moody periods, I try to keep afloat and positive. I've been seeing a psychologist to help unpack some of the feelings that I've shoved aside for decades. I'm also learning to be kinder and less self-critical; a trait common in many Singaporeans. Recognising that I am doing my best during this tough period is already a step in the right direction. I'm also trying to change the way I think to help integrate into my current self the hidden parts of Isabelle (e.g. her vivaciousness, friendliness, curiousness), so that when I eventually emerge from this vulnerable phase, I'll be a lot more comfortable with my identity.

(I still sometimes wonder if I am Transgender, based on the usual metrics)

One thing I struggled with before starting HRT was whether I was truly Transgender. Even after popping those tiny blue pills twice a day for more than a year, I still wonder if I am "Trans" enough. The self-doubt is significant, and justifiably so. Transitioning is by no means a simple undertaking, with large financial, social and possibly health costs. It is literally shooting a bazooka to your old life and what is recognised as "normal". The constant and recurring critique is the brain's way of protecting oneself from the whims of the heart.

But it isn't just about the "worth it or not?", "cost-benefit-analysis" line of thinking that I tend to go into when making big decisions. The constant thoughts of whether I was "Trans" enough also stems from having lived as a guy for 3 decades with some degree of success. While I am by no means an Alpha-male, I did successfully navigate male adolescence and adulthood without too much trouble. And I feel quite comfortable existing as a regular Singaporean working adult male, Husband and Dad. So how could I possibly be transgender? Some questions that I had considered and still do include:

How can I be transgender if I don't hate my male genitalia?
How can I be transgender if I enjoyed doing "guy" stuff, and was perfectly functional as a guy, including during my army days?
How can I be transgender if I was never effeminate?
Did I just allow my fetish of women's clothes to take over the steering wheel?
Is wanting to transition a superficial whim?
Do I want to transition, or is it the rose-tinted hope that I can be successful like the very small number of transgender women influencing me to also want to transition?

Apparently, such self-doubt is common among people who transition after their 30s, as they have lived through a good part of life as a guy. Even by stretching my imagination to its limits, I still struggle to think of how I was going to unlearn all the male socialisation if I were to transition socially (aka let the whole goddamn world know I am Transgender).

I found three blog posts from the same author that resonated with me greatly. With decades of living as a guy and external reinforcement of her gender as "male", the writer described that acknowledging she was transgender felt like believing a conspiracy theory about herself. Like me, she didn't fit the popular, accepted narrative of the feminine, young transitioner who was absolutely certain of their "Trans"-ness, and that continued existence as a guy will cause significant distress. To the writer, being a guy just had a lot of feelings of dissociation rather than distress. The writer also saw it necessary to describe how she realised she was transgender (her most popular post. Read it!) and write a guide to help people figure out if they transgender, which I found incredibly useful.

I've come to terms that I am transgender, although I think the self-doubts will remain until the cat is fully out of the bag. A friend shared that as I come out to people and transition socially, I will gradually figure out which parts of myself are armour that I had put on over the years and which are core. And Isabelle will slowly develop over time.

Right now however, I don't even know which parts are armour that my male self had learned to be so comfortable wearing and which parts are core. Every part of me feels core! It even feels like when I fully transition, I'd still be 99% my male self, that I'd just be pretending to be Isabelle and co-opting feminine mannerisms not because that was truly me, but because it matched my new exterior and society would be more inclined to accept me if I behaved that certain way (Jokes on me, society will always brand me as transgender, with all the associated negative labels). All this however, is conjecture based in worries for what the future holds. Only time will tell how Isabelle will be like when she has been fully let out into the world.

I wrote about how my mental state hasn't been the best 9 months into transition (around February this year), and keeping it healthy was a constant struggle.

Well it seems that things haven't really improved. My mental health has been in the pits. Here's one of many similar journal entries that captures the rut my mind has been stuck in almost everyday.

For most, the transition journey isn't an easy one. It's like travelleing through a pitch black tunnel that you know is around 2 - 3 years long, but feels like forever while in it. You have no idea how much longer before you get to see the light and there is significant uncertainty on whether you'll even reach the desired end state.

Seeing others successfully present female in under a year on HRT also cuts my soul repeatedly with little tiny blades. I rage at why my own journey is so slow, even though the logical mind knows that my starting point is different; I began transitioning at a later age, my hair transplant was done around the 6 month mark so growing my hair out takes a long time, facial hair removal took longer than others who were less hairy, and removal of deep icepick acne scars takes multiple cycles.

To make things worse, dissonance from needing to present the opposite of my desired gender puts a constant mental strain. It has been 14 months since I started HRT and I still present as male flawlessly. I feel nowhere near being able to present as Isabelle. In the office I work mostly with guys in their 20s to 30s, while at home I still play the roles of son (to my parents) and a father. It is no wonder that I feel so damn far away from my goals.

I am most vulnerable and susceptible to my intrusive thoughts when I'm tired. When the dark clouds come, I can feel myself becoming this insufferable ball of grump; my brows furrow often, the tempers roil just under the surface and I'm one random trigger away from lashing out. On other days I feel so physically and mentally drained from work, Daddy duties and the brainworms that I just lie down on the bed for up to an hour, hiding from it all. I've had to constantly remind myself to be patient with others, be present with those real in life (i.e. my kid and wife), and be kinder to myself instead of brutally piling on more self-guilt.

(Me at the end of the work day)

I have been able to identify some of the common triggers that causes my brain to slide into that doomspiral of bad, unhealthy thoughts:

Seeing my reflection in the mirror
Hearing pretty transwomen fret about their near non-existent masculine features
Seeing other transwomen successfully living as their female selves (never mind the fact that they started years before me and went through a similar journey as I am now)

Unfortunately, I cannot avoid looking at my own reflection in the mirror on a daily basis, so this is one trigger that I have to live with and just trust the process. But reducing other sources of triggers did help me to feel less shit about myself and manage my emotions. I left a Discord server of local transwomen (though they were my friends), because their occasional bouts of fretting over "masculine" features was a massive trigger. I also stay away from Reddit r/transtimelines and other online transgender spaces, where people post their before and after photographs.

The solution is quite clear, albeit an extremely annoying one; Patience. I need to wait another year for HRT to take its effects, for electrolysis to remove my facial hair thoroughly so I no longer see the beard shadow and for my hair to grow out to a length where I can cut it in a more feminine style. Once I can see more of Isabelle in the mirror, it might just help soothe the dysphoria further. If I am still unhappy with my appearance, I could then consider facial feminisation surgery (FFS) to reduce the prominence of masculine features.

To help me manage my mental state and address my anxieties, I've also been seeing a psychologist, which has been surprisingly helpful in reframing how I viewed things, as well as pointing out a number of my blind spots.

My anxieties had roots in childhood and adolescence, where my self-worth has been tied to external validation, compliance with conventional measures of success and what a "Good" Boy/Man/Male Singapore Citizen should be. The thought of stepping out of this box by being transgender is triggering a ton of fears and anxieties, because of my internalised shame.
Just because I can rationalise my fears and anxieties doesn't mean that the emotions are not there. It is important to acknowledge these uncomfortable emotions, understand why I feel them, and work on being more self-compassionate instead of self-critical.
I needed to work on separating my self-worth and from my perceived ability to pass. I am worth it and there is nothing wrong in trying to express who I am. While I fervently desire to pass, it is about wanting to feel safe (read: accepted) in society and about being in control. However, this is dependent on others. Continuing to tie the chasing of this arbitrary target to my self-worth will be detrimental to my mental health.

These actions have helped me to manage my emotional state a little bit and tide over the darker moments. Hopefully with small wins as I continue my journey, I'll eventually get to a healthier place mentally and regain confidence for Isabelle to reappear in public.

(This post is probably going to get me cancelled 😕)

Captions of "Estrogen is magic!", "Estrogen is pixie dust!" "Estrogen is crack!", followed by a side by side pre-transition photo of a man with facial hair and a post-transition photo of a long haired woman with makeup are so incredibly common on Reddit r/transtimelines that it is almost the norm, yet it masks something incredibly important; Estrogen is not a magic pill.

I hate how misleading such captions are. If you look at most of the pre/post-transition photos posted, there are usually the following key differences:

Short vs long hairstyle;
No makeup vs a full face of makeup;
Obviously male vs Definitively female attire;
Way better posing and expression for the post-transition photo;
Original face shape vs Post-FFS face shape

How are ANY of these changes due to starting on a regimen of Estrogen? (Answer: NONE!) So why are the photos being labelled as such? Being able to look female is more than just the bodily changes brought about by taking Estrogen. Many other factors play a part in helping to be recognised as female.

To be fair, I can understand the euphoria one feels when transwomen compare their current post-transition selves with the man they once were. Being on a regimen of Estrogen (and anti-androgens to keep the T-levels down) does help many, many transwomen feel better about themselves, gradually bring about subtle feminising changes to the body, reduce gender dysphoria and feel optimistic about life. So it is natural to want to show the outcome of an amazing journey, especially if the pre/post-transition photos are so starkly different (and also for the dopamine rush that Reddit upvotes and Instagram likes bring). I did feel a sense of optimism when I saw how my body has changed over a short 6-month period, knowing that there are more changes to come. But I can assure you that after 1 year of HRT, the reflection I see in the mirror is still that of a unkempt long-ish haired man with a subtle beard shadow.

So far, the transition photos that I find most useful are shots taken of a person in the same position, month on month, showing the bodily changes over time due to continuous intake of Estrogen. It takes a bit of discipline to take such photos over time, but the almost clinical documentation helps to capture the subtle, but truly magical changes. The gradual fat distribution helps to make the body look more feminine, even if the subject's post-puberty skeletal structure is broader than typical cis-women, gives other transwomen who just started their transition hope of what is to come.

Estrogen's use in HRT is one of the means we take to achieve our end goal; to help us come closer to becoming the woman we feel so deeply to be, so that we can eventually let out the inner woman we have painfully suppressed for so many years. So transwomen, do continue to share with the world your amazing transformation journey on social media. But please, please try not to mislabel your photos and call Estrogen a magic pill, when the the changes aren't primarily due to Estrogen. Hopium is a terrible drug, and baby-trans are awfully susceptible to it.

Musings of a Singaporean Transgender

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