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JenniferRM comments on Non-obvious skills with highly measurable progress? - Less Wrong
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This seems likely to be controversial but I want to put forward "sales". Every so often I wonder if I should spend several months in a job like selling cars, where things are presumably really stark, but so far I've generally ended up doing something more kosher and traditionally "geeky" like data science.
However, before I knew a marketable programming language I had a two separate "terrible college jobs" that polished a lot of stuff pretty fast: (1) signature gathering for ballot measures and (2) door to door campaigning for an environmental group.
Signature gathering was way way better than door-to-door, both financially and educationally. Part of that is probably simply because there were hundreds of opportunities per hour at peak periods, but part of that might have been that I was hired by a guy who traveled around doing it full time, and so he had spent longer slower cycles leveling up on training people to train people to gather signatures :-P
Sales is objectively measurable, but it is not easily measurable. At least, for big ticket items like cars, the sample size is small so there is a lot of noise. It is easy to measure whether one person is better than another, but it is harder to measure continuous progress.
I credit an undergrad summer job in door-to-door sales for moving my social skills from "terrible" to "good". For that particular job we literally had a points system that was visible to everyone in the office (and determined incentives like fully-paid vacations abroad), and you'd sell enough on a daily basis that you knew roughly how you were doing (ie 5 sales was a decent day, 10 outstanding, 2 bad, out of perhaps 100 interactions), so it was a near-perfect training ground.
I did just this. It was rather difficult, but my confidence and communication skills did improve quite a bit.