My personal plan is to have the transition fairly well established before I start coming out in a major way, because my wife and I feel it's a more concrete way to explain and be understood -- "you may have noticed some changes; well, there are more changes to come, because this is what's happening with me," versus "here's this really disruptive feeling and plan that I have, that you can't see any actual evidence of outside of my asserting it," if that makes any sense. It's hard, especially with co-workers, whom I'm closer to than most of biological family, especially since the bulk of the transition plans are only plans until my wife is firmly and securely pregnant with our third child, so there's not a lot it feels like I can do except talk and think about it. I feel a huge pressure to say something, just to get it all out of my own head a little bit, and maybe to an extent, to legitimize it, but realistically I don't think it's the time.
I don't know whether this is relevant or not, but when I went through an earlier period of fairly major gender dysphoria, for a variety of reasons I didn't do a whole lot of actual real-world crossing of gender lines, and I did talk an awful lot about it to my friends, and looking back, I'm not sure that was altogether helpful. I think it created a feeling of "put up or shut up" among some people, and when it turned out that a transition wasn't in the cards for me then, it made me feel like a huge failure, and like the gender dysphoria was some sort of delusion that I just had to put aside and push through. It's been hard getting over that feeling now. That's my experience, anyway. I hope you find a balance that works for you, and much happiness and comfort as you move forward on your own path, wherever it leads you.
-L