Have you asked him what he failed at today? His goal should be to fail at something each and every day. (If you don't fail, it means you have not tried or attempted. Each failure is learning taking place.)

Read the story of Sarah Blakely:

http://www.makers.com/moments/embracing-failure-0

http://www.levo.com/articles/career-advice/sara-blakelys-spanx-failure-helped-career

http://www.bloomberg.com/bw/stories/2007-11-21/how-failure-molded-spanxs-founderbusinessweek-business-news-stock-market-and-financial-advice

Yes he does play piano and he loves it.

Does he play an instrument or is he in scouts?

My DS whenever given new problem/challenge he does it wrong, almost always gives up. But if we keep prompting him step by step he does it. He does not try above/beyond. I feel like he does not use his potential to fullest .Not sure how to treat this problem. He has low self confidence, does not trust himself, when asked question about in group of kids he always falls behind, but otherwise he is very smart child. Understands new concepts quickly, asks very meaningful and thought provocative questions.
He is in AAP (was not in pool, but WISC-iv secured IQ 130) Doing well in school.
Very weak in organizational skills. I am afraid if this continues he might not achieve as much success as he deserves.