This comment of yours reminded me of an episode of The Twilight Zone (80s version not the black and white one). I remember the story but not the title. I had to look it up. The title of the ep is "One Life, Furnished in Early Poverty". Your paragraph, more or less, describes the premise of the story. It had an interesting twist at the end.
Btw, the episode was based on a story by Harlan Ellison, who as you know wrote "The City on the Edge of Forever". So I guess this isn't completely off topic. There is a connection to Star Trek.
I rambled on too long already. If you are, or anyone else is interested, you can probably see it on youtube.
I'll check it out. Thanks!
It's also going kind of into "Tapestry" (TNG) territory. "If I'd been more like I am now... " I guess everything happens the way it does for a reason and that's how you learn in the first place.