I've become a far more confident and far less timid person since highschool. Dunno what incited the changes, but I do know that if I were like how I am now back 20 years ago, I'd be living a very different life now. Thing is I dunno if the updated me is better or not, I'm just more comfortable this way and less nerve wracked.
Basically, i can't see the future so I don't know what's a better approach to life, we just need to do what lets us remain happy.