When it starts to seem like transition will begin now, no matter what. When you just can't bring yourself to pose as female anymore, and just find yourself slipping naturally into the male role, and really liking it. When it all just seems inevitable, and you know you're going to be a lot happier.
I've been putting off transition for at least 10 years. Didn't want to deal with the hassle. Didn't want to be more of a freak than I already am. But I don't think I can put it off any longer. I can't keep pretending to be something I'm not (and really suck at even pretending to be). I need to stop hiding from the world and fooling myself. Here I am in a very trans-friendly city. What better time and place to start transitioning?
I've been in contact with a therapist who works with trans people. I think I'm really going to go through with this.