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[quote=Anonymous][quote=Anonymous]Oh one more thing, is it possible to volunteer part-time in the field he wants to be in while continuing to look for work?[/quote]

Yep, he's been volunteering part-time in the field. Learned a lot but no job.

He's worked closely with his undergrad admissions office. Lots of advice from them, but no job.

He has done all the things one is supposed to do, but ... no job.

I guess that's life though, you can do all the right things and still fail. I just thought that if you're really smart and worked really hard and have an Ivy league degree and were incredibly successful at a challenging job with stellar references, then it wouldn't be so hard. Our classmates from college don't seem to be struggling (to be fair, they probably did a better job building networks while we were introverts with a really small circle of friends). 
I know plenty of people who have quit jobs without having another one lined up (they call it funemployment) and easily got back into the workforce.

Ultimately of course the answer is just to get a job that he doesn't really like (and there's been some interesting suggestions in this thread, ranging from corporate finance to waiting tables) but I guess he's not ready to give up on his dream yet. So I need to do a better job supporting him for a while longer. 
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