I've actually tried this approach. He is 34 and seems to be in a "I'm too old to change anything now" mentality. I recently heard about a job I knew would be perfect for him and got in contact with a friend of mine who works there. They are apparently looking for staff so I told him to drop a resume in. He mulled it over for a few days then decided not to because he didn't want to risk the security of his current job that he hates. Wouldn't even go to an interview. I'm not sure how much more I can do to bring him out of this funk and I blame the ham entirely for keeping him this miserable that he doesn't even see that there are better options for him.