I think the thing that's not obvious to young people is that choices that seem good at any given time may turn out to be poor choices further down the line. The guy who traveled the world while working one hour a day telling engineers what to do over email probably had a great young adulthood. It sounds like he paid for it later, though, by getting laid off and having difficulty finding another job.

This doesn't mean that those who worked their asses off didn't get screwed over, but on average they probably did better professionally - and by proxy, financially.