My concern too, Stephanie. I'm 58 and just starting. I've lived in the same house for 30 years and we have a very friendly neighborhood--good for crime prevention, hard to stealth transition. I'm working at a company at a job I love. The bottom line is I have to transition in-place and I'm dealing with my concerns: I don't want to be the neighborhood or work "->-bleeped-<-" (and I use that word advisedly and deliberately), and I don't want relations with my wife's family to suffer. But, my biggest worry is whether I can really own this. 58 years of putting "me" in a box makes me wonder if I can ever relax and be genuine, open and confident. The woman I see in my mind isn't beautiful, or svelte, or sexy. But she's confident, put together and a lot of fun to be around. And I worry about my shame, my secretiveness, and my total lack of self-confidence now.
I can do the logistics: the hair, the face, the weight loss. I'm not sure about my ability to become that woman, though...