This might work better for a tech- / web-oriented person, but it's certainly worth trying. I would encourage him to start a blog, with no set agenda about what

This might work better for a tech- / web-oriented person, but it's certainly worth trying. I would encourage him to start a blog, with no set agenda about what he writes about, but with a goal to write for 30 minutes a day about whatever he's interested in, or to link to articles / videos / other blog posts that deal with things he thinks are interesting. Then, after a month, to look back, and to see what common themes emerge. It might take some creativity to then morph that into a job, and if he doesn't have sufficient motivation to explore all of this without your help, there might be little you can do, but I think your interest in helping him is commendable, and I hope you're able to help him find a good path.