While Janis might have sang, that 'freedom's just another word for nothing left to lose' she was most likely wrong. I know all sort of women who have done very well. Lawyers, executives, professors, even craft persons. I know all sorts of guys who sat wondering 'why?' when the real question was always 'why not?'
For years I was, as you were with the hippies. To a degree I still am. What scared me then, and scares me now as I see another crop coming along is just what you describe. Lots of lost little indians in that tribe. They wandered from place to place, from person to person, from drug to drug until it all caught up with them. But there were many who asked that 'why not' question and if not finding a way out, at least found a way through. In the seventies I know several who took the path I did, into and through entertainment, where the rule were somewhat lax. But I also know a bunch who were the original freaks at Atari and Apple, smoking dope, listening to the Dead and writing code. They had that anchor, that thing they wanted to do, write code, or put on the show, or just sit and study.
I've lost a lot of people in my life through crossdressing and gender play. Some were pretty important to me. Its just that in keeping my eyes open, I've gained just as many. In all desolation there is a measure of liberation. So I wasn't going to be a big hit at the office with my painted nails, my clothing choices and mannerisms, I managed to find a place where no one cared about it, or even kind of liked it. Or in doing research and writing, I found that the books didn't care at all, and the words on the printed page did not carry that onus with them.
With or without GID, if its severe or mild, life will go on anyway. And you have to find a way to keep on living, and if you can find a way that is not just mere existence, that might provide you a life, isn't that better? Isn't it a positive to think that you don't have to wash your life in drugs and crawl out of that hole? And indeed, your the lucky one if you found that way out, for most its a one way death trip. I don't want to see another generation walking the streets of the tenderloin looking for crack, or drunk on cheep vodka, or all methed out and tweeking. I would like to think we can teach and encourage success just as easy as we could teach and encourage failure.
I'm not great white hunter, I just liked money. I thought that money could (and it did) provide a certain level of if not freedom, at least security. And you obligations, no matter how you come to bear them, are your obligations. Living up to them, regardless of who you are, or how you are, is just part of being human in the greater world.
Karl Marx once said that history repeats itself, 'first as a Tragedy, and the second time as a Farce." And we, in this community, everyone from drag queens to crossdressers to TS are crossing that borderline now. Where what happened to a lot of us was tragic, what's going on is moving a different direction. As more and more TG persons of all stripes find success, its going to be a lot harder for those that do not to find sympathy.
In our own ways, many of us have been a part of that. Making it all OK. But it makes the road that others have to follow a bit harder in some ways.
So sure, plan for your HRT, or SRS, or find a place where you can express yourself, but be sure that you also have to have a life plan, goals, a way to make it in the world, GID or not.
The roles you take on, the roles you play, the roles you choose are not set in stone, but they all have consequences, many of them long term.
For those who take some sort of counter path they get to invent them, but those that want to mainstream their lives, will be required to play by the same rules as everyone else.