If you haven't achieved anything, you haven't got anything to be proud of in the first place. You can't go backwards from step 1. I don't care when I lose at street fighter, or if my player rating sucks compared to my friends' - I'm not good at street fighter yet.
And believe me, if you think it's difficult to take risks now, at ~25, without children to feed and send to school, without a girlfriend who requires upkeep or friends with high-paying jobs who want to eat at Michelin restaurants... you're never going to get off the boat.
Every journey begins with one step.