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Humanities in academia is just as bad as human factors. The biggest thing that can help is having a shitty low paying job or two early in one's career. And then working formal a stable, normal company where there is real mentorship.
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The biggest problem with humanities in academia is that they sometimes seem allergic to epistemic humility (which I guess was Feynman's critique of parts of the humanities).
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When I say humanities, I mean having a humanistic attitude. Looking at the social and environmental dynamics before looking at any specific technical issue in detail. Not necessarily anything to do with academia.

Strong agree that everyone would benefit from having a shitty service job or two when they're young to learn what life is really like for most people. I worked a bunch of different service jobs in high school and college, it's shocking how poorly most people treat someone just because they're standing behind the counter.

In the corporate world I find it's usually very obvious who has real life experience and who doesn't.

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Which Hamming quote, btw, do you refer to? I think he mostly talks about talking with other "smart" people, and communicating what you are working on a lot (like giving talks, etc.). But, this doesn't read like much of a case for the humanities, per se.
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I always thought that an Engineering degree with an MBA is a very good combination. You get very practical, useful things when you are younger. Once you have acquired enough life and work experience then you can appreciate the subtleties of cases that you study in an MBA.
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Two degrees with practically zero education in the liberal arts, humanities, or philosophy. You're missing a big chunk there.
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