This seems to me like the opposite of the typical ambitious young person’s plan today, over filled with extracurriculars, prestigious degrees, and well-worn paths to success. You’d think that Jobs’ success would lead to more people trying to emulate his roundabout path, at least superficially.
Maybe you could make the argument that Jobs was just too unique to serve as a role model for everyone else. And the labor market is a lot different today vs. back then. But I do think that his apparent lack of institutional hyper-optimization contributed to his success in a fundamental way.