Someone said something very interesting on the Metafilter thread. Dilbert is not the hero of the series. Think about it, he's a loser who fails at everything he does. The hero(s) of that series are characters like Dogbert, Catbert, Wally, the PHB, etc who all succeed despite being massive douchbags. They do what they want, and get away with it. Even when Wally was fired he still came out on top.