Our expert says:
I think one is entitled to a mid-life crisis at almost any age. OK, maybe before puberty would be a bit excessive.
Regretting what you did ( indeed, forgetting what you didn't do ) is remarkably useless activity. Learning from both, to plan what you WILL and won't do in the future, is useful.
You cannot, now, enjoy a different adolescence - that opportunity has past. But the more time you spend looking over your shoulder at the past, the less you will be ready to make better use of current and future possibilities.
I think psychotherapy would be a reall good idea, to review what can most usefully be learned from the past, and apply it to a more satisfying present and future. The images you have in mind ( pirate, philanderer ) are of states that are satisfying only in fantasy, and rather grisly and unpleasant in reality. Exploring how to find better opportunities to build on your excellent successes, and include more lasting and worthwhile satisfaction, would be a better way to go.
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