This question grew out of a reaction I had to Rob Wiblin's "Consider a wider range of jobs, paths and problems if you want to improve the long-term future".
While reading, though, one thing struck me as a question that merits some more attention. I quote:
I suggest paying a bit more respect to the courage or initiative shown by those who choose to figure out their own unique path or otherwise do something different than those around them.
Given the entrepreneurial slant of EA culture, I worry that some people will end up concluding "we should celebrate risk-taking even more than we already do".
I wonder whether an EA who is encouraged by this might be more likely to underestimate how costly entrepreneurship is, and whether it is in fact becoming more costly to the individual?