Will gwern ever get a formal job? (not just contract work) by 2038?
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he's been self-employed since at least 2011 and I see no indication that he has been anything else other than self-employed

Would appreciate some clarification on resolution criteria. Full time job? Contract? If I paid him $X to complete some task would that count as a job?

Your last case sounds v much like 'contract work' to me

Oh I see, the title was edited to clarify, fyi

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