<p>I disagree to let him fail, especially a fourteen-year-old boy. Boys need direction and help to organize, attend to details, and get things done. Don’t go for that stuff (because it’s easier for the parent…) that it’s his decision, his choices, his life. His brain is not even finished until age 20 or more. I am not saying don’t be hard on him–quite the opposite. I’d showed him you are “in there” with him, lots of positive reinforcement on the topics (not sports) that he is good at, explain to him sports management these days take at least some college (I have a niece who is going into it and she’s studying some finance and management in college at a specialized school). AND, he may well be BORED. So many kids I know of who don’t do well in school, and MANY hugely successful people that are interviewed, say they were bored at school. Public schools are largely little challenge and are taught in a very boring way. Find a subject he has a passion for and cultivate that. People take boredom as laziness or a disability, when the kid needs more challenge and an interesting setting/way of teaching/learning.</p>