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mrogers: As my boss puts it "...in the type of IT work we do, someone with a degree would just be an over-educated idiot."

Another way of looking at that is that your boss believes he's getting a bargain, and frames his flattery of you in such a way that would become an insult, if you increase your market value, in order to discourage you from pursuing what would be most financially advantageous to you. Whether or not he is such a manipulative prick, much of that analysis holds, regardless of his motives.