I've been coming out to one person at a time since mid February through private conversation. I've confided in a least a dozen real life friends, and my sibling.
Before this year, I swore I'd never tell a soul about this. After seeing a therapist on a monthly basis since the beginning of this year, however, I'm a lot more comfortable in telling people.....without shouting it from the rooftop, of course
So far, almost everyone I've talked to seems to be supportive and 100% behind me. I'm quite aware that I'm going to be dealing with people who are going to flat out reject me, if not get hostile with me upon revelation. Nonetheless, I'm not going to let anyone hinder me or stop me in the big picture.
However, I must admit that I'm terrified to come out to the rest of my family, as I'm quite aware that they'd have an absolute fit. I'm in no position to be kicked out of the home, nor am I in a great financial position to be able to get out on my own and transition right away. Therefore, the next few years are going to be a test of my willpower.
Coming out to family I believe was the hardest part of transition. I hope it goes well for you. :)
Your family may surprise you. I was terrified of coming out to me, but they have been really supportive. It wasn't easy with my parents, but certainly not what I thought would happen, and they are by my side.