I think this maybe reflects less on the generation than societal (their elders'?) expectations of human beings and separating a person from their resume.
Everything is a ladder now, boxes to be checked off on an HR form.
The person optimized for "interestingness" and feels they have very little to show for it. I'd bet that was also the case for quite a few "interesting" people in the first half of the 20th century.
Maybe I'd have a richer life if I'd spent 2 years as an animal tamer or whatever, but society isn't set up to reward that. Was it ever?
Everything is a ladder now, boxes to be checked off on an HR form.