That sounds awfully depression-y. I'd encourage him to talk to his doctor, if that's at all possible. Could be that he just needs an SSRI to kick himself back into gear. Or maybe not, but it's worth the conversation.
Whoops, maybe it came off as more dramatic than I intended but I meant mostly work-wise. He's a pretty happy guy when around friends and family. It's mostly a "what am i doing with my work" unhappiness, that he seems to be actively avoiding. He works from home, so he'd ditch it all to go snowboarding instead. Not that it's a bad thing from time to time, but it feels like his productiveness has been on a steady decline. He admits it too, and says he doesn't feel like doing what he's doing. Which is also fine - people change and get tired of certain things - but it feels like the point where some kind of change is needed. The problem is he doesn't know what he wants and just sticks with the slowly declining status quo.