This is less an indictment of "the system" than further evidence that systems can be gamed. Is this a shock to anyone?
Our narrator seems to have coasted through a variety of moderately prestigious (an adjective meaning that other people think whatever it is must be very discerning) opportunities. He chose to squander them out of a seemingly nihilistic/angsty/meta-hipstery and extremely adolescent rage against the machine.
What a pity. For him.