I had a lot of fear, shame, and guilt that prevented me from transitioning years ago. Fear that transitioning wouldn't "work" for me, that I'd lose my friends/family. Shame... I was raised catholic in a poorer, very homophobic/transphobic neighborhood. I hardly hang out with any of my old "friends." Guilt - for some reason I thought something I did in life was why I felt like I did.
And of course, worrying about "what others would think."
What helped me out was massive introspective meditation, a few near death experiences, and soem world traveling. I traveled Africa for 3 months, visiting friends in Peace Corps, lived with one for 2 of those months in a very rural village doing subsistence farming.
Before my travels, I had much anger and bitterness inside of me, and fear. Sometime during my trip I became aware that life is good, and that my purpose in life is to be myself. I had originally planned on expatriating as a way to escape the pressures of my life, but while over there I became thankful for all of the great aspects of my life, and found that there's no need to escape from anything, only a need to create the reality that I want to see.
Sorry, this is a long post. After seeing so much death and suffering, a midst simple, true happiness, something clicked: I had been putting myself through suffering, I was a big ball of hate and anger and frustrations. I let it go, and opened up my heart.
But the story doesn't end there. Fast forward to just over a year and here we are. I have started transition, but I am not entirely out. Ok, rewind again. I am very lucky to have met a a great friend. I have met a few people like him in my life so far. The best description is a visionary or psychic. So a year ago when I made the decision to live my life and transition already, he and I were at a bar. (We had lived together in the past and I was his manager at work, we were very close) He told me that about 2 years ago, when he was living with me, he had this flash vision of me in the future, but I was a woman. I was suprised, and told him how since I was a little kid... {skip this part} and teased him, "why didn't u tell me 2 years ago!"
So the first person I came out to, well they came out to me first. That made it easy. Back to the future/present now. So I'm not 100% out, I'm doing it where I tell the closest people first. The people I want to be in my life, the ones I love, the one's I'm close to. Highschool acquaintances, gradeschool buddies, do they really need to know? I don't think so, in fact, most of the people I worry about telling the most are people I don't really hang out with ever, we never talk, we have drifted apart and the only link now is facebook. I'm completely cool with telling the people I care about as I transition, and once I'm good and fulltime, well the rest can find out through the grape vine. If they have questions they can ask me. My standard ending line for coming out is.... and if you have a problem with that or have anything not nice to say, well I don't wanna hear it and you can never talk to me again.
I hope my novelette will help you.
Oh, the introspection/meditation stuff. Sometimes I just know things, it's a nice gift. Whenever I don't listen to my self, bad things happen. There's no doubt that my self is female, and that she wants me to be happy, and to share my love and happiness with the world. For the longest time I kept her prisoner, was not happy, and did not share any love, but instead spread hate. I didn't even love myself. Now that I have accepted myself and began to love myself, all of my past problems like anger, or drinking/drugs has stopped.
I would hate to make this any longer. I hope my words will help you. I've heard such great and inspiring stories from the others on this post. Many, if not all of us were in your shoes, coming out isn't easy, but once you do that feeling of the weight being lifted is so great. I have had nothing but positive reactions, but like I said, I'm cherry picking the people I tell. I get the feeling that some people have got me figured out, and they have distanced themselves from me, so perhaps that counts as a negative, but they were negative people, and to me, losing a negative person is something positive! I wish you all the courage and strength as you move forward