For what it’s worth, a lot of it seems to be a symptom of social conditioning. Many of us are taught from an early age that gender is linked to biological sex, and that anything other than expressing the gender you were assigned at birth is wrong.
I remember when I was a kid in a religious school, we were told constantly that transwomen were just gay men who were trying to “trick good Christian men into sin”. It got worse as I went through the grades, and expressing any doubt or dissent got me hauled into the headmasters office for the usual round of detention and threats of eternal punishment. I tried on a skirt at the uniform store once and my parents almost disowned me.
That was reinforced by the 90s and early 2k media. I distinctly remember an episode of one of the police procedurals of the day (Law and Order I think) that portrayed a transwoman as this lying, manipulative monster who tricked her husband into the marriage and did all sorts of things to pretend she was cis before she got murdered (which the show heavily implied was her own fault for lying about being AMAB).
The whole experience did a wonderful job of scaring the life out of me and preventing me from even considering expressing my gender, no matter how miserable it made me to be seen as a male. I did my absolute level best to be what society expected from a male, and felt disconnected, depressed, and wrong the whole time.
Thing is, when I came out to myself, I had a full blown panic attack over the realization, because the programming is still there. That toxic voice in the back of my mind (not a literal voice, obviously, but you get the idea) does periodically start shouting that I should just stick with the program, that it’s too late in life, that it’s not worth the effort, I’m never going to pass, I’m never going to fit in, that being miserable and towing the line is easier, etc.
On a related note, if you have a moment, read up a bit on cult conditioning and how it causes even the most sane and reasoned individuals to avoid questioning things that blatantly make no sense (i.e. living as a male when you know in your soul you’re a female). You’ll be alarmed at the parallels between the mindset of people going through deprogramming and people who are working on coming out.
It’s natural to question your transition when you’ve lived your whole life being told in no uncertain terms that you can’t be yourself. The kind of damage that does depends on the individual, of course. Some folks didn’t swallow the Koolaid as kids, to keep the cult metaphor going. They were strong enough to be secure in their identity, and no one was going to tell them otherwise.
I’ll be the first to admit, I wasn’t that strong. I desperately wanted to fit in, to have friends and be accepted. I had bad knees, couldn’t play sports, I was a nerd, and bullied fairly constantly for being feminine and weird. It didn’t help that I’m adopted, so I was dealing with all the baggage of trying to figure out why my biological parents didn’t want me (it’s hard for a 10 year old to wrap their brain around the incredibly complicated nuances of adoption).
So I accepted my role as a male and did what I thought I had to do. I was petrified that if I stepped out of line again, I would be left entirely alone. That fear scarred me deeply, to the point I still haven’t been able to come out to my parents because I’m afraid of losing them. So, yes, I question my transition often. Not because I don’t know who I am, but because I’m afraid to lose what little I have left. I know it makes me a coward, and I’ll cotton to that, but… the fears are very real, and I’ve had enough misery to last me 10 lifetimes.
Anyway, that’s my long winded, rambling, and borderline incoherent view on why some of us question our transition and also somehow a coming out story? Sorry it got so long, it all felt relevant when writing it.