Needs to think of things bigger than himself

 

He has the ability, but lacks the will, so he sabotages his own success.

Success entails a lot of work and responsibilities.  He might sense that he cannot maintain that level of energy and courage to sustain the success.  He might also not be confident of knowing what is out there and feels comfortable under your protection.

Just trying to help finding out what the problem is, which will lead half way to a solution.

 

There are children's version of the Bible, for different reading levels, some of them can be for a quite dense reading.  He should be able to handle it.  It is not for any religion but for knowledge and world view.  He'll be able to understand deeper a lot things happening out there.

Book "The American Revolution: a Visual History" by DK is a good overview.  The founders are colorful characters.  A lot can be learned from their biographies.  He needs to affirm his identity by knowing the ideas so that no one out there can say he is any less than what he wants to be.

Book "Philosophy for Kids: 40..." by David White.  It expands and organizes his thought process so he will be able to handle more complex issues.

Travel more.  Visit more historical sites and learn the stories behind them.