I read the $36,000 job as the one he was now aiming for, but hasn't found yet. I.e. that, failing in his attempt to find an entry-level position in a finance or business type setting (the sort of high-stress, high-pay, 70 hr/wk "ambitious" route), he's now turning his sights towards a "lifestyle job", a 40 hr/wk, $36k job at a ski resort or that kind of place.