You can also prime the pot a bit if you know areas of interest where talent and passion lie. If you know the other arenas of interest, you can focus conversation on how good he is at these and how wonderful it is to see him considering jumping into other things, encouraging him to try those alternatives, etc. A brief experience: I have a friend who only wanted to act - and was TERRIBLE. But she is a great photographer. Every time we got together I took the opportunity to admire her pics, suggest her for theater PR shots, etc etc. I actually helped her find work as a theater photog on several occasions. Over time, she found more and more work as a photog - and interestingly, also became a better actor - and while she now dabbles in theater, she makes her living doing graphic work.
(And, as an aside - GRRRR that people who hate it are taking those touring gigs and many who would love them can't get in the door.)