If I had to guess, it would be the author's apparent desire to "optimize" life -- specifically by optimizing how much you will be paid, or how you will be perceived by others. For example, he states "right now a degree in computer science is a ticket to a decent life," with the implication that it's not unreasonable to study computer science solely as a means of achieving financial security. So the depressing aspect is the thought of people directing all their energies towards "gaming the system" as effectively as possible.
As usual there's a balance to be struck. I've had my fair share of years spent chasing whatever fun thing I was into at the time. I don't regret those years at all, they were fantastic and they've contributed to my character far more than many other pursuits.
But there's still nothing glamorous about not having enough money to cover basic expenses, unexpected emergencies, to live in a comfortable place, to be able to afford the transportation that will get you to your passions.
I would not be worse off if I had abandoned some of my dreams a little earlier and pursued money for a little while longer.
That's as much because of the young age as anything else. When I was in my early 20's I still wanted an edge at literally everything. Conforming to that, of course you'll be championing your "career hacks" as hard as you can, because it's such a large element of pre-adult success culture. It just took another 5-10 years of living(I'm 30 now) to settle down and find an approach and goals that actually fit me.
