As a philosophy major he should be seeking the truth. And the truth is that a philosophy degree will generally get you a job that does not pay very well.
He struggled to come up with the $300 a month he owed. The first work he found after he graduated from the University of Northern Colorado in 2011 when the recession's effects were still palpable was on-again, off-again hours at a factory, unloading trucks and constructing toy rockets on an assembly line.
The truth should now have been obvious to him.
He then went back to school to pursue a master's degree in comparative literature at the University of Colorado Boulder.
But as you succinctly put it, he doubled down on stupid by following a philosophy degree up with a masters in creative writing.
And he has still not found the truth.
but he said his difficultly finding a college-level job in the U.S. has made that debt oppressive nonetheless
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this is the money-quote.
a college level job. What the heck is that?
You work and you make your way.
Your character determines the jobs you obtain.