This article was discussed in the Private School forum (if you venture there, put on a helmet). Somebody posted a hilarious cartoon but I'm no good at copying images, so here's a link:
http://i.imgur.com/jxlDs.jpg
I've read that article and also some previous articles by the same author.
This author has a shtick: he went to Columbia for undergrad and his PhD, then he taught at Yale for 10 years, and now he thinks he wasted his time because he can't talk to his plumber. I'm not sure why exactly that is, or whether he has some other problem, but anyway he blames his lack of ability to talk to plumbers on his Ivy education and Ivy career.
He concludes, without any personal experience that I can tell, that other colleges (SLACs, public universities) are more intellectually stimulating because they are more diverse. I don't think the numbers bear that out - SLACs are full of full-pay, upper income, similarly privileged kids. And public schools have their share of sports-obsessed and frat-obsessed kids. Every Ivy is a scrum of pre-law robots? And every SLAC is an ivory tower paradise? Really?
The author also tends to exaggerate, which is a time-honored academic tradition of course, but he takes the hyperbole a little too far IMO. For example, I agree that lots of kids today are afraid to take risks. But the way he says it, it sounds like every kid in every Ivy (and all Ivies are the same, of course) is afraid to take risks. Also, I'm pretty sure that fear of failing exists in similar measure among the kids scrambling to get into the SLACs he glorifies.
Also, he doesn't always make sense. Take the quote that OP copied about waiting tables. I was a waitress, and it's tough. But they way he puts it, it sounds like he's saying that people should choose waitressing which is a more noble profession than going to college, and God forbid you ruin your life by spending it in academia. Meh. Different strokes for different folks, different careers for different people.