You don't want to be the one who didn't believe in James Joyce and booted his ass out of the house before he was successful, that's for sure. Is there a particular thing he is trying to be successful at, or is he just throwing shit at the wall to see what sticks?

I also agree with Laurel. This couple has been together 20 years. They have a child together. Yet it's just assumed that this guy is just sitting around changing channels all day and always has been. Without more information, we don't know that.

As for him getting a job...Laurel is right there, too. This isn't 1999. Nobody is hiring now, and if they are, they certainly aren't hiring people over 40 who have never had a permanent job in their lives. Being out of work for more than SIX MONTHS is enough to disqualify most people now. And have you looked at some of the odious "personality tests" they administer for new hires for menial jobs, which involve snooping into every possible aspect of your personal business? Even getting a job refilling the egg trays at Safeway involves passing one of those things, and they are picky picky picky about who they call for an interview, let alone actually hire. They can afford to be, after all.

I mean, the LW can't get a job either, and she HAS a good work history. Remember? It's not like it used to be. Noobs have a hard enough time getting a job; old noobs, forget it.

A better idea would be to develop some kind of business using the skills he has right now that he can use to get some extra cash in a pinch. Can he fix stuff? Clean houses? Take pictures of babies? Mow lawns? Do spreadsheets? Take requests at a piano bar? Babysit? A lot of other people are looking for that kind of work, too, but if there's something he's really good at, it's probably a better idea for him to develop a sideline business doing that than trying in vain to get himself hired, which is not likely to happen any time soon unless someone he knows has an "in."

Also, he may be more of a mental health risk than he or the LW are letting on; the pressures of having to knuckle under to a corporate boss very well might kill him, even if he could get hired. Don't laugh. Artists commit suicide (with conscious deliberation or otherwise) over not making it, and was it Allie who said getting that kind of job would signal to him that he had failed and there was no hope for him? I assume LW (and their kid) would rather have him alive and not employed than see him take his own life or drink or drug himself to death.

They need to progress as if he has been looking for a job and can't get one, because really the end result is likely to be the same. Sucks, but a lot of people are in that boat.