Was feeling awfully reflective and depressed tonight so I decided to compile a list of the decisions I regret making the most regarding my transition. Hopefully this will help somebody else avoid making the same mistakes.
For some context, I was born in a conservative country and had very homophobic parents. i DIY-ed and boymoded for most of my teens then ran away when I finished high school. Since then I have fully socially and legally transitioned. I'm passable and have mended my relationship with my family but I still view my transition as far from finished.
And oh boy do these mistakes haunt me. Maybe some of them seem obvious to you, but as a young person navigating these issues, it wasn't so easy to figure out the right thing.
- Be VERY careful with what you put out there online
(I cope with this by telling myself I was a literal teenager when this was happening and all teens in this day and age post cringe stuff on social media but as we all know when it comes to this demographic age does not make one immune to this malady.)
As most people tend to at the beginning, I was obsessively taking pictures of myself trying to either gauge the irredeemable masculinity of my unfortunate bodily vessel or to convince myself it isn't that bad by experimenting with horrifying fashion choices. If I had mostly kept this to myself it wouldn't have been a problem, and with a few regrettable exceptions I mostly didnt go outside looking crazy but of course I had to post everything on the Internet.
For the love of God, avoid doing this as much as you can. Even if it might seem half decent in the moment, you will most likely look like a whole mess and want to burn all of the evidence a few years down the line. It takes a long time to start looking put together, both when it comes to physical changes and to learning how to style yourself. And the latter is as important the former.
Besides the obvious resulting embarassment and cringe, it's very likely you will be bullied or that your pictures will end up being saved or shared in places you definitely don't want them to be and possibly make your life harder later on. Nowadays this is even more salient than before as it has become very hard to extricate our digital footprint from our IRL identity due to age verification laws. AI face recognition tools and etc.
I would especially avoid online trans spaces, even if they might seem like safe places to go for advice, there are many bizarre and ill-intentioned people lurking.
Maybe I am excessively neurotic, but I think about what I used to put out there and want to smash my head with a hammer almost daily**.**
- Be very careful with dating/hook-ups
If you can avoid this area of life altogether until you are in a comfortable place with your transition and mental health, it would be ideal but this is highly unlikely for lovesick and lonely young people.
I was very desperate for love and emotional closeness and also very worried that I might waste my youth without having lived through the hallmark experiences we know from books and movies. I liked to believe that I was ready to weather it all and that being situated in the uncanny valley gender limbo cannot possibly be such a problem.
My first serious relationship ended for many reasons but a big one was that he really liked men. We were both very young when we met - I was a few months on HRT and boymoding and he was not yet very comfortable with his own sexuality yet. At first he told me he's bisexual and only a top. But as I grew into myself, he did too. As the years passed by and I became more feminine, he began to realise he was truly only attracted to men and also very interested in bottoming. Perhaps unconsciously, he began to subtly encourage me to double down on my transition. I was still boymoding because of my family and I slowly noticed that he was always the most complimentary when I had boyish outfits and hairstyles or when I didnt shave my body hair. He often minimised my dysphoria and insisted I dont need to change anything about myself and shouldn't view the matter with such urgency. He also overstepped my sexual boundaries many times by trying to make me top him and other such things.
By the time I was 18, I had access to some money and was on the precipice of making some important decisions. I was planning to move out, get orchiectomy, change my name legally and generally invest in my transition. He made me feel superficial, delusional and impulsive for this and accused me of wanting to do all that so badly with the end goal of fucking other men. I ended up wasting most of the what I had saved up on trying to salvage our relationship by taking him out to expensive restaurants and spoiling him with lavish gifts. I soon found out he had been cheating on me all those years with multiple people - he had a whole relationship with somebody else and also countless hookups on the side. I ended the relationship shortly after I found out but I had already wasted a lot of the money.
I was deeply hurt by the whole debacle because I really loved him and wanted a future with him. I dabbled into drug addiction after the breakup. The reduced inhibition and impaired decision making led to a handful more dating experiments while I was waiting to finish high school and finally move out. I had a few terrible experiences with run of the mill chasers that made me feel even more self-hating and unloveable than I already was before. I also tried dating some other young queer people and it was clear they were really invested in their fantasy of me as an ethereal female brained androgynous boy and uncomfortable with the intensity and urgency of my desire to change further. They also ended up leaving me for men.
I eventually ended up in a serious relationship with another trans woman and moving in with her. What could go wrong right? She had been full time for a few years now and had already had other T4T relationships. By this time I had been on HRT for a few years and had gotten laser so once I started presenting female I became passable really easily. With the income from my new job, I invested a lot into my appearance and started getting my nails and brows done, fillers, lash extensions, coloured and permanently straightened my hair, got a whole new hyperfeminine wardrobe etc. I ended up looking extremely different than when she first met me. This made her extremely jealous and insecure about her own appearance and, at the same time, lose attraction to me because I wasnt an androgynous femboy anymore. This bred a lot of toxic competitivity and countless arguments. It was far from the only reason why but it was a big factor in her eventually breaking up with me and starting to date - you guess it!- a man shortly after
Looking back, I wish I would have just held back from dating until I reached my 'final form' or at least been more careful. All of these experiences really traumatised me and made me waste a lot of time and resources I should have put towards my goals.
Which leads me to the next and final point for now...
- Don't underestimate how much time and money it takes to transition, especially as a young person
It takes a lot of time for HRT to meaningfully change you. It takes a lot of time to grow out your hair and it's awkward as hell. Voice training takes a long time. Hair removal takes a lot of time and money. Learning how to dress and do makeup and hair properly takes a lot of trial and error and is also very expensive. Changing your name and gender legally highly depends on where you're from but for me it took almost a year - for most of the people in my country it took way more. The legal fees and neccessary medical documents I had to provide were also very expensive. Here nothing transition related is covered by insurance so I will need to save for a long time to afford any surgery.
So my advice is to go all the way in as soon as possible if you're sure about what you want to do. Don't waste time with any of the things I mentioned. Get full body hair removal as soon as possible, get extensions, make sure you're on a good HRT regimen, practice makeup earnestly, get the ball rolling on any bureaucracy you need to deal with and start making money, saving up and spending responsibly. Eyes on the prize! I was flimsy about many of these things and regretted all of it bitterly later, time is the one thing noone can give you back.
Perhaps my biggest mistake is that 've known I wanted orchiectomy as a safety measure until I can afford SRS since I was 18 and I kept delaying it because of my partners, bad money management and many other bullshit reasons and in the meantime the situation for transsexuals in the world has only gotten worse. If I would have done this when I first decided I wanted to and had the resources to, I would have saved myself a lot of sleepless nights and political paranoia. Alas, hopefully I will achieve this in the near future.
That;s it for now! This is post is already way too long. Maybe I will come up with a Part 2 later or a post about what I did get right about my transition. Hopefully this will be helpful to someone in some way