Where to start?

VA is useless. I wouldn't bother wasting your time talking to them. Have him look at the local job services location/website for something he can manage. He'll likely need to step outside if his comfort area to find something that pays the bills. You should serif he'll look around, but the self-starter, leader-type mentality that the military instills in us is applicable to so many aspects of management and just different types of jobs that wouldn't normally come across his mind. But now he's not pigeon-holed to a certain mindset or sectorif the workforce, and can branch out. Something. I didn't quite realize myself for a long time after I separated. Maybe show him this response and see what his thoughts are? My school has a VETS office which helps with college and career planning, and always have their ears to the ground for new vet-friendly jobs that are cropping up. There's no reason to stick with a shitty job because it's a step backward, not using the military experience as a stepping stone, and most time it won't pay the rent. Get him to sharpen his resume (maybe pay someone professional to look it over so he has the best foot forward) and get apps/resumes out there to everyone possible.
If you do show this to him: dude, the ball is in your court. You've got a good girl who cares about you and is trying to help you be the best you can, because you're fucking capable and you need a kick in the ass. Take it from the former E-5 who is barely scraping by: you have every tool available to you. The only reason you don't have a job is you're not advertising yourself well enough or you're not trying hard enough. Push harder, and you can rest on your laurels once you're making bikini bucks. Til then, keep pressing on and find a path that will suffice for now.

Gonna go get another drink but don't end up in a shitty corner wondering where the past three years went. Be proactive and get your ass out of the house.

/r/Veterans Thread