Maybe, for the first few years, but really, when you think about it - isn't Dilbert just a loser? He never improves his lot, he either has no desire to, or no ability to. If no desire to, he is a loser. If no ability to, he is under the mistaken impression he is far smarter and more capable then he is, which means he is also a deluded loser.
(and yes, I know its a cartoon !).
But it does bug me a bit - instead of people feeling sorry for themselves (as the cartoon seems to help people who are coping with grey corporate existence) why not encourage people to change their environment (either bit by bit, or just improving yourself, starting something, finding something, anything).
Dilbert is a loser, feel sorry for him but don't relate to him or else become him.