Hi Elanore,
Wow. Your question is so huge that I barely know how to respond. To be honest, I hardly ever passed as a boy. Not to suggest that I'm some stone fox or exceptionally feminine in appearance, only to say that I never integrated well as a boy. For the most part when I was young people assumed that I was gay. I tried really hard to fit in, but could never really get there. I finally gave up trying in my early 20's and became extremely androgynous to the point that people who didn't know me couldn't be sure if I was a boy or a girl.
Did being trans effect my education or career path? Being trans has dramatically effected every single solitary aspect of my life from my earliest memories. I was an angry barely functional teenager, bored at school and rageful with the world. I did have a small posse of girlfriends who knew that I cross-dressed, and we would get together and play dress up sometimes; that was fun. Perhaps my little girlfriends were the only thing that got me through my teen years.
If you really want to know how being a trans woman derailed my early life in a big way, well, I joined the US Army when I was 17 years old. I thought it would make a man out of me. Soon after arriving in Germany, I sought out a therapist and told her that I wanted to be a girl. For 2 years I met her twice a week and we talked about it. She was awesome. Then I got sent to Texas where I sought out a new therapist. This one was not so awesome. He outed me. Word spread quickly throughout the base, and a very serious attempt was made on my life. I ran for my life and evaded the FBI for the next 10.5 years. (I eventually turned myself in and escaped with a general discharge and my life.)
Those 10 plus years that I spent hiding from the people who wanted to kill me (just because I'm trans), well, I just can't fully express how far off the rails my life went from what I had expected I would become and accomplish. Nothing about my life has really been what I expected it would be since.
Don't get me wrong, I'm not complaining. I love and adore the woman I've grown up to become. I would not have missed the wild and crazy adventure of my life for anything. In the early years of my life as a fugitive, I learned from a very wise man that success is measured by the joy we achieve. I learned that lesson well. And I have devoted my entire life to the pursuit of joy. I have made every effort to eat well, to think well, and to focus on the positive aspects of my life and of everything around me. Focusing on the positive aspects of everything has become a habit and my way of life. It has served me very well.
To quote John Lennon's song "Beautiful Boy", "Life is what happens to you while you're busy making other plans." Life is always going to put obstacles in our path. Those who suffer the most are the ones who either ignore or willfully run into life's obstacles and then cry "poor me!" Those who have the greatest shot at living a happy, joyful, fulfilling life are the ones who learn to go around the obstacles and relish whatever it is that they discover around the unforeseen corners. Or so it seems to me.
May the adventure that stretches out before you exceed every expectation for how you once believed your life would turn out.