I was always a very non-conforming person in general. I never liked sports and never pretended to. I used to respond to people who wanted to talk about sports by mentioning figure skating, which I legitimately think is beautiful athleticism. Some people would assume or accuse me of being a gay man, which is ironic because I'm actually a lesbian woman.
I originally tried transitioning a decade ago. First I was wearing a combination of guy's clothes and girl's clothes. I would try little things one at a time. I would frequently wear eye liner and I was able to pass off as "goth" as an excuse when questioned. I came out to some people at the time, and they didn't understand what I was trying to say. I never used the phrasing "woman trapped in a man's body" because I felt my body was a woman's body with deformaties. I quit because of lack of acceptance, and the pain of laser hair removal was too scary for me. My approach at the time was: clothes first, facial hair removal second, and I would have gotten HRT next.
I resumed my transition last year. I completely abandoned all men's clothing (except underwear because of comfort). I came out to every person I could, including everyone on Facebook. I tried to find HRT as quickly as possible and got it after a ton of effort. I did some electrolysis and it actually left marks badly enough that the electrolysist asked me to give HRT more time before continuing. Currently, I don't have a clear plan for access to SRS but I want it ASAP.
So the summary is, doing a gradual shift a decade ago didn't work. Doing as much as possible with maximum effort now is working.