I came out organically without any announcement to family, eventually, I had to speak with employees and contractors at my company but they basically knew before that. I just talked to people ad-hoc as the conversation came up. I live a city of 50K people, so I see people I know all the time and I live downtown, so that anyone who comes downtown to shop or eat is bound to run into me.
I never really understood or cared very much about what was going on behind my back. Indirectly it probably cost me money as people judged me and decided to go arm's length on business relationships etc, but thus far I have continued to support myself.
It's been a bit confusing for some (even some friends) as to how I present myself sometimes changes pretty drastically. Last year it was getting more and more feminine, this year it is on the masculine side of feminine or more androgynous. I transitioned to alleviate mainly social dysphoria and that mission has been accomplished, and now 4 yrs into the future I have to make my way in the world. As a trans person, that includes wearing what I want to wear or not wearing that which I don't.
The thing is is that I am the same person I've always been, I never considered my gender presentation to be that important in the grand scheme of things and the fact that some people are uncomfortable with this change in society with more openness, more acceptance and more fluidity, the fact that it challenges categories and understandings about the world that they grew up in, is not my issue. It's their time to catch up not mine. I'm sure there will future changes in the world that I will have to deal with too.
To those struggling with stepping out, I really do have empathy. More so, I have some disdain for some parts of the world/culture that makes people feel fearful and not fitting in. My advice to others is to plow through and be the person they are, everywhere.