If we are trying to base a self-evaluation on a self-created hypothetical about what we were "supposed" to do, we are almost always going to come up short. That is because "possibility," my favorite category, is literally infinite, and our personal capacities, of course, are not. Within the world we most immediately inhabit, everything is "possible," though not simultaneously, and if our freedom to choose has led us to do and accomplish some things, and not others, we have not "failed" to do the things we have not done, we have just not done those things, and have done other things, instead. I don't much like the expression, but it does have some applicability in this context: "It's all good."
To me, at least, an inclination to be grateful for the life we have lived is a very potent antidote to the "angst" about all the things we haven't done, or didn't do. That antidote to a sense of personal angst and crisis works for both men and women, and it works in late and middle age, and it even works for young people, too.