If he is on medication for anxiety, will the military (any branch?) enlist him?
My DGD had a recruiter tell her not to let them know she had been on medications in high school! She tried, but after one week she was processing out.
Our community college has a course for students that helps them find their interests and strengths in different fields so they can find a vocation they are well suited for. Maybe instead of a full schedule of classes he can focus on one that will help him make decisions on a course of study... Ksm