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Because a lot of people don't want everything resting on them. Takes a special kind of person. I know I ain't one. My dad owned his own business with a 100 employees and it was miserable growing up

> I don't have any solid theories as to why

What sees you discount the obvious? That is, formally educated people end up in formal education because they have a proclivity towards not wanting to have to go out and get it. They want someone else to hand it to them. Which is, after all, what the "formal" part of formal education describes.

Have look at Nassim Taleb’s Skin In The Game. He explores this topic at length.

The problem is identifying what to go out and get. Because most people will go out and get the wrong thing and end up burning themselves out of future endeavors.