Definitely have a case of the jitters. It’s unnerving it can be to make a risky conscious decision that you could theoretically continue to sidestep.
There’s also some concurrent transitioning going on in other ways, probably the biggest is that I’m stepping away from the fundraising group I’ve been involved with for years when my term as a board member is up in September, and I’ve only been nominally involved the past few months aside from being there for board meetings. Partly, I’m just a bit burned out with them overall (drag queen/gay men drama). Partly, it’s one of the board meeting are one few places where I still show in male mode with people I know, and that’s becoming increasingly uncomfortable. (The logistics are a little tough, but I’m probably going to start attending the meetings as a woman.)
Partly it’s cutting ties with (the vast majority of the) people who knew/know me as a man. (While folks in the burly community obviously know I’m male-bodied, with a few exceptions people there have only met me as a woman.) Even if it feels right to choose to back away, there is a sense of loss of community involved.
On the other hand, feeling in control of my approach and timing feels really important despite no shortage of anxiety.
While it might seem like I’m on a relatively fast timetable, I’ve got plenty of time to plot my course, time to maneuver and adjust as needed. (OTOH, it’s not really that quick. I blend well enough that if I wanted to transition well enough I could do so next week — albeit with greater difficulties, in particular my voice, while much improved, isn’t where I’d like to be yet and would definitely be a “tell.”)
Part of it is lingering insecurities about authenticity and “realness.” Currently I feel like I’m still a bit gender-fluid, but it’s between “woman” and “not man” — if that makes any sense. Or at least stereotypical “man.” I suppose one reason I felt more at home in gay male circles was that there’s a greater latitude of gender expression (not just drag queens). OTOH, there’s other aspects that I just find wearing.
It’s also going to be a little harder for me because unless I want to cut my ties to the burlesque and kink communities there are going to be people who my past. Not that it necessarily will matter to them, but knowing that they know may matter to me.
But one things that’s always helped me with these sorts of anxieties is cutting straight to “what’s the worse that can happen?” — and if I’m OK with that, then I don’t need to spend (too much) timing worrying about the intermediary anxieties. ‘Course it helps to be able to limit the worse case scenario to one that’s reasonably realistic. I.e. things might go sideways at work, but I’m fortunate that I’m in a field that in strong demand, so I’d land on my feet. So I’m trying to keep myself calm.