"With dh, I stopped sympathizing and started playing devil's advocate."
with this person, I try to do more encouraging and sympathizing, because to do otherwise is very demoralizing for this person. And this person is very easily demoralized, so it ends up being a LOT of cheerleading on my part, which is getting tiresome.
This person also has a very overrated sense of himself and his abilities, and applies for jobs like CEO, etc., without even having a four year degree. So I try to just encourage as far as "you're a great friend" etc, instead of focusing on the job stuff, since it is seriously so far beyond his abilities and everyone can see that but him.
He's 40 now, and is still at the bottom of the barrel as far as job seniority goes. He does want to go back to school, though, so I see that as a positive step.