He's unrealistic about LIFE

Okay... So my friend.. He is in jail right now... This is his 3rd time in there.. Hes 23 and he is unrealistic about life.. How do I get him to mature his mind. I UNDERSTAND you cannot make someone think how you think. And women mature faster than men... But he thinks when he comes home from jail that he can get straight into business school and he wants to buy and sell houses... He thinks it will be cake. I'm glad he has goals.. But with his record and lack of job experience.. I feel like he doesn't realize how much work needs to go into this .. And once he does realize... He'll quit.. Cause that's the kind of person he is.. What should I do? I don't want to tell him his ideas are bad!