A note to someone who is over 60 and thinking about the energy lost in putting family first and not transitioning in the past, the “time wasted and diminished productivity” :
The way stigma works in the world is like a brake, all that social pressure around you creating friction when you start to do something that is off the norm.
Like a brake, it changes forward motion into heat, burning off energy rather than letting it drive you on.
You regret that the energy you feel in your life got burned up and wasted rather than being used to empower and invigorate you. You wonder if breaking through, if presenting as a woman, would change that dynamic, allowing you not to waste and dissipate valuable energy, energy you feel you have already wasted way too much of in succumbing to the friction of stigma rather than breaking through.
I encourage you to do what you need to do, to heed your calling and follow your bliss. Times have changed in the world, and the stigma about trans is much less than when you were a kid.
But I do want you to know that stigma still exists, and while transitioning is enervating, there is still stigma.
When you first come out as a transgendered person, you spend your first year in absolute euphoria. Then reality sets in, and you have to make a life and deal with the stigma.
Joan Roughgarden, New York Times, 2004
You may well unlock lots of wonderful bits of you if you are out full time as a transgender woman, (or even as an androgynous man, as you sometimes fancy you would like to be, though I doubt that is really you.)
But the tethers that hold you — the family you committed yourself to — won’t go away, and neither will the stigma, even if it happens in a different way than it does now, more externalized and less internalized. Dumping your trans nature into the world means you don’t have to police yourself in the same way, but it doesn’t mean you won’t be policed.
Leap, yes, find your bliss, yes, but don’t beat yourself up for losing energy to the presence of stigma in the the world, burning energy as heat rather than motion because of that pressure.
That’s gonna happen however you present.