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One of my best friends is very similar to yours Shokan, he was always a little "off-center" but in the past 5 years or so, he's done things like moved to BC with nothing but a backpack full of books and clothes to his name and couch surfed while working and quitting a variety of minimum wage jobs. He then lived in a decrepit VW rabbit through the winter in Toronto. He moved back here to live with his parents last year, to save up money to live an even more bare-bones existence in Mexico, but has since quit another job to focus on doing yoga all day.
I've found that flat out telling him what he's doing is crazy and serves no good purpose. His parents are furious that they spent a small fortune getting him through university and he's done nothing with it, and he often purposely makes things awkward between people by being deliberately controversial and confrontational. I just don't think he sees any of that as being important.
The best I'm able to do with him is be the voice of reason. If he gets wierd, I listen, but try to play devil's advocate for him. If you make your friend think about how he plans to live, at least you'll know how serious he is. But if your friend really wants to go, let him, he'll be back come winter and he'll have probably cleared his head somewhat.
Don't know how much help I've been, but I hope a little at least.
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