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.
I'm not telling you how to live your life. Please, feel free to take ridiculous risks. Give up all your worldly possessions and move to the SF bay area. Start boring web 2.0 apps. Do a startup or whatever. Go to burning man. I'll be over here enjoying my nice, stable life.
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.