So, he wants to have a talk, does he? Well, let him talk and you just listen for a bit. It's going to be one of those talks that you may need to keep quiet at first and then come back and revisit later.
No one knows what he wants to do with his life. He doesn't know himself. Right now, he's wallowing in depression and feeling sorry for himself and the mess he's gotten himself into. He's paralyzed and can't move ahead. He's like the hamster on the wheel that goes round and round with no stops in between.
Step totally back and let the wheel turn until he gets tired of running on it.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.