I'm lucky in a number of ways:
* I'm financially secure. If I lose my job because of transitioning, I can just retire a little early, and still have enough to pay for any surgeries.
* My company is large enough that they actually have a policy somewhere on transitioning. (I found a link to it on our company's website, but I don't have the permissions to read it.)
* I live in a fairly tolerant part of the USA (NYC area) and so far nobody has batted an eye seeing me in "women's clothes". (I'm only just starting transitioning, so I don't even begin to pass.)
* The non-work communities I spend time in (Contra Dance, Unitarian Church, Chorus, etc.) are open-minded and in some cases actively welcoming.
* I'm divorced and haven't gotten grief from my ex. (I'm pretty sure she knows, but we haven't discussed it.)
* My kids both know I'm transitioning, and are okay with it. (Basically, they're "whatever. When's dinner?")
* My parents are dead, so I don't need to worry about coming out to them. (And anyway, we were never all that close, so I don't think I would have been devastated if they'd disapproved.)
* Family has seen my gender non-conforming dress and not said a word. (It would be out of character for them to get all worked up about it anyway.)