I can see how my advice could be read the wrong way in this post-shame world.

No, I do NOT mean "be an asshole if you feel like it".

I mean it more in the latter sense - take a vacation, go to Pompey. Say hello to the girl you like and see what happens. It's something you can do now, so later you don't replay it endlessly, wondering what would have been.

Also, no billionaire right in the head will be bemoaning not having more billions while on their deathbed.