Rather than going "back to college" I think we need to find a way to bake it typical to just always be taking a class or two.

Maybe it takes you a decade to get that degree, maybe you end up not needing it, but taking classes is better than sitting around in meetings all day. Besides, the security of not being pigeonholed in a single career is going to make people less fearful and more likely to take risks like starting new businesses.