Well, I would definitely bring it up with your therapist and tell them your plan on coming out to see what they say, see if they agree or have any suggestions to improve it. They would definitely know you better and know more about your situation than we do so they can probably offer better advice.
However, it is your journey, your life, and you can do it however you'd like. There isn't just one way to do things, you can do it anyway you'd like, whatever is more comfortable and best for you.
I totally get what you are saying though cause I totally thought about doing that too, letting others just sort of figure it out and approach me about it. I was thinking about it all the time, about how I would say it, to whom, and what kind of questions would they ask and what I would say in return until I just got to the point where I like literally HAD to tell someone so I did, a few actually in a pretty short period of time. I always over think things too and found out I was guilty of it again because none of those conversations were anything like what I had thought they would be like when I was playing them out in my head.
As for the others that I haven't told yet? Having gotten that need out to tell someone I like no longer feel the need to tell anyone else atm so I ain't lol. I have had a few people call me out recently on some changes that I have been making, weird looking facial hair thanks to laser, shaved body, longer hair and basically just told the truth when asked bout it but so far nobody has added everything up and popped the question so I haven't told them yet, but I will if it comes up.
If you are not sure yet or not ready to do it then don't, there is no hurry, it is not a race, just take your time and do it when you are ready and want to.
