I think it's a lot simpler than what you describe. The most important thing is to maximize enjoyment. Obviously a lot of factors go into this but at the end of the day the end goal is to enjoy your life as much as possible.

It depends a lot on how you're wired, of course. Enjoyment maximization for some people might be getting married, having a bunch of kids, being the head of a household. For others it might be accomplishing career goals or financial milestones. For others it might be adventure, to seek out new experiences, etc.

The biggest trap you can fall into is living life by the standards of others instead of your own enjoyment. That's what would likely lead to regret. I'd say to some extent (for me at least) there is a local optima to be reached where you aren't the subject of ridicule by others, but beyond that you need to take a firm stance towards identifying what brings you the most enjoyment and pursuing that relentlessly.