You should be able to identify this by the fact that he brings up a lot of stuff and actually cries and then also gives up. He might be very low, maybe even suicidal. Hes stuck in a job he clearly hates and probably feels there is no way out. I do not know how to solve this. Something needs to change with his job or find something else. You should summarize his symptoms psychological and physical together and at least give him some life advice. Maybe that is all it takes.