Perhaps some of the readers here saw it from a mile away. Some may say, "See, I knew she was going to transition". For the latter, please keep your opinions to yourself. Insisting that someone is an "egg" when a person is still questioning and struggling with gender identity is forcing a person into a mould and extremely unhelpful. Remember, breaking eggs from the outside harms the cute little birdy inside. The little birdy needs to break out of its egg by itself. 

The thought process went something like this. Maybe I could stay on a course of estrogen without letting my family or colleagues know and I could eventually have a body that was more female. Maybe the estrogen and testosterone blockers will finally stop my male pattern hair loss and even help some of my hair grow back. Ooooo, softer skin from taking estrogen? Sign me up! Wait but this is a serious decision that requires some thoughtful consideration. Oh but remember the lingerie advertisement you saw on Instagram where the model filled up the cups so nicely? That could be me! But seriously. I'm in my mid-30s, looking like an uncle most of the time with a receding hairline and I'm thinking of transitioning? I must be out of my bloody fucking mind. I'm not going to look like the girls I follow on Instagram. It's more likely that I end up looking like a weirdly feminine version of my current male self, in a gender limbo. Why do I want to crank life's difficulty to "extra hard"? (this is the logical side of my brain screaming at myself not to proceed). But the other logical half of my brain tells me that the changes are gradual and can be managed. There's no harm in giving it a try for a while and if necessary I can always try to hide the more obvious changes in certain ways. And hand on heart, I really do feel like I want to be female and seen as want. My brain was vacillating between "yes transition" and "no transition" at such speeds it was giving me mental whiplash. I had to stop myself, try to push the thoughts away and distract myself with work/kid. But this time was different. The floodgates had opened, the toothpaste was out of the tube. My metaphorical egg had cracked and the yolk was making a goddamn mess everywhere.  

Transitioning will be a massive shock to my parents who have zero clue that their son actually wants to be a woman.

First up, there is the logistics of hiding all the changes from them in the initial stages. I foresee that in year 1 and 2 it will not be too difficult but beyond that, how am I going to hide the physical changes from my family, especially two prominent changes appearing on my chests? While I can potentially bind my chest when I am at work and wear thicker shirts, my parents are likely to wonder about things, especially my dad who is quite perceptive. I also plan to grow out my hair, which will get a lot of questions on why I am looking unkempt. While the excuse of wanting to sport a manbun might cut it (barely), it will get repeated commentary and raised eyebrows.

At some point I will need to come out to them, which goes on to part 2; managing the fallout. Will my parents be disappointed? Will they feel like they have failed as parents? Will they think that I have lost my mind? Throw into the mix Asian expectations of me being the eldest son of the eldest son. Although it might be very difficult for my dad to accept this change, he has recently expressed that we should take action so we do not regret things in life, so I think I can explain to my dad logically my reasons for doing so. It is a coin toss though, since he is quite the traditional Asian father. As for my mother, an extremely devout Catholic whose life revolves around church, I can already imagine her going into shock and plunging deeper into church life, hoping to pray it all away. Doesn't help that the Catholic faith does not view LGBTQ folk and activities in a positive light. I also see her occasionally harbouring some anti-LGBTQ views, though knowing her, there is a lot of blind belief in that area. She is oddly strong in certain circumstances, but also emotionally fragile in others, so once again it is another coin toss on what the outcome will be.

I know some transgender folk are like "If they don't accept, f*** family", but I think this is not for me. I have a good relationship with my parents which I want to maintain. So I need to do my best to help my them accept that I am still their son, even though appearances wise I will look less and less like one. 

I can imagine how family gatherings will change in the future. Perhaps I will be the transgender family black sheep, the pariah who is automatically "uninvited" to all future events. Honestly I don't care if they don't want me around, but I'm more concerned about the hurtful words that they might say to my parents. I've set myself a goal that if I present as female, I will do what I need to in order to be my best self, and as undeniably female as I can be, to reduce buyer's remorse. 

[Post note: I have been told that such thoughts are very common in baby-trans. To be pretty so that people will not judge. But the reality is that society doesn't care. If they have it in their mind a negative perception, there will always be some imperfection that clocks you as "Male" that cannot be magicked away.]

Supporting myself is also a big issue. How is this decision going to impact my work? While I don't think I will lose my job as a result of this choice, the organisation I am currently working in is quite...traditional. There are also quite a fair number of Muslims and Christians, so views of transgender folk are likely slanted to the negative. While I plan to present male in my professional life for as long as I can, there might be a point where I am no longer able to hide the physical changes, or my views may change and I want to present as female. How will it affect the way I perform in the office? Deciding to transition will definitely slow promotions or close off certain job roles, since having a transgender leader might cause some discontent in the ranks. Bosses tend to also be of the older generation, so they may not want to work with someone deemed as "不男不女 (neither man nor woman)". 

I think I have enough money saved to last a while, but in terms of transferrable skills or networks that makes me a choice hire regardless of my gender, well that is uncertain. I do worry that my decision to live as someone true to my heart will screw up my finances in the long term and jeopardise the rest of my family. This decision could very well be the costliest decision of my life, and I'm not even factoring in the impending medical expenses and surgeries that I may have.

On the bright side, this has lit a fire under me. In 2 to 3 years, the changes will be difficult to hide, meaning that if I want to present female professionally, I need to make the necessary moves to change to a job or organisatiom that is more progressive. This means that whatever skills I need to pick up, I will need to do so now.

While medicine continuously improves, medical science on transgender issues are lagging by a good number of years. This is simply economics; there isn't significant money to be made in researching transgender related medical issues because the population is too small.

Being on HRT for transwomen means taking estrogen and anti-androgens for life, and like any other drug, taking it regularly and over long periods does result in increased risk. A poor hormone balance results in increased risk of osteoporosis, and nobody really wants that. Another known risk of taking estrogen orally is an increased risk of stroke or Deep Vein Thrombosis (DBT), as well as greater stress on the liver due to the need to process the hormones, causing endocrinologists to be more conservative when prescribing hormones. While understandable, this leads to some gatekeeping by medical professionals. But the more fundamental issue is this. If I do this long term, would it really lead to poorer quality of life due to health issues when I am in my later years? (Uncertain. I need to read up more on this topic. So far it seems that the benefits of transitioning outweighs the costs). 

The other worry is insurance. The stance by insurance companies is unclear and can be quite varied. While some transfolk have made medical claims without too many issues, others have reported that their insurance policies were voided, despite having paid for YEARS. While it is understandable that there is now a potential increased chance of claim (due to say, higher risk of breast cancer for transwomen), this is really quite bullshit. People don't get their insurance voided for suddenly picking up smoking or drinking like a whale. Having this uncertainty with regards to insurance isn't great.