I've thought about this, and you know? I think that, at each stage in my life, I did the best I could have under the circumstances at the time.
And, actually, I think it's less due to any perspicacity on my part and more due to my nature: I'm really lousy at turning myself into what other people expect me to be. So my path has always been more or less guided by my inner nature, my "inner voice," because I simply couldn't follow other people's directions. And however confused things may have been at the time, when I look back on my life, I have the impression that my steps have been guided by someone who is a lot wiser than myself and has my best interests at heart.
As I've gotten older, especially since I decided 15 years ago to try to be myself, I've gotten better at listening to my inner voice and trusting that it will lead me where I need to go. I think it waited until conditions got safe enough in the USA and my part of it before letting me be aware that I am trans. It gave me plenty of warning that I was going to transition. It told me that it was safe to come out to my pastor; I guess it knew better than I how supportive she and the congregation would be. It told me when to come out to a coworker and to my boss and HR.
But even before, when I was still agonizing over whether I was a good person, a good husband, a good employee, a good father (well, I still agonize over whether I'm a good parent), still at every juncture in my life my choices would slowly clarify as if a fog were lifting, and I would see how some would lead to life and some would lead to just marking time until death, and since I didn't want to die, I'd choose one of the "to life" ones. My inner voice was looking out for me even then. Even in the Hell of my childhood, when I could not see how I could stand another day of that life, something told me: hold on, just hold on. When you're 18, you'll be able to get out and things will be a lot better. (Not that I had much choice -- I was too scared of death to kill myself.)
I don't know what the future will bring, but I've learned not to worry too much about what I can't see to do anything about. I have this warm sense of trust that my inner voice will lead me the right way (or a right way), and when it comes time for me to breathe my last, my inner voice will be with me to tell me: you've done good, it's time to let go.