Right now I have what by any criteria would be considered a good job. I'm paid decently, I have basic benefits, and the position is as close to Stable as jobs get these days. Yet I'm not happy because I'm expecting the job to make me happy. I expect it to not suck, when in reality on many days it does suck because it's a goddamn job. Nowhere was I promised that it would be rewarding and fun all the time, or that it wouldn't be frustrating, or that I would have days where I come home and wonder why I bother. I bother because they pay me, and getting paid is very useful to me. But that's it. That's the deal: I show up and fulfill my responsibilities, and then I get a check. Nobody said anything about fun.
As often as I give this advice to other people, I give it to myself lately. What I can't figure out is why people in my age group (or younger) have this idea that the task for which they get paid will also be personally enriching. Is it because we lack fulfillment in our personal lives? Is it because we're spoiled, believing that the working world owes us self-actualization in addition to a means of supporting ourselves? I'm not sure. What is certain is that we should be careful what we wish for. Those factory jobs that no longer exist start to look pretty appealing as our Career-as-Spirit Quest theory runs into reality.
I'm not sure if he's just asking rhetorically, but I'll answer. Speaking as a fellow Gen Xer, we had that idea because it's what we were told by our parents. You can be anything you want (so it better be something suitably impressive)! Hell, when it came time for us to be summarized for marketing purposes, it was presented as our defining characteristic: we were going to be the first generation to not exceed our parents' standard of living, ominous gong. It was an absurd, ahistorical delusion to think that such lifestyle customization could keep endlessly going onward and upward, but there you go. I blame the Enlightenment.