I liked this advice too. I think it is an interesting counterpoint to Jeff Bezos's "Regret Minimization Framework," i.e., take the path that is least likely to leave you with regrets.
What do you do about a path that scares you a bit, and is also more likely to leave you with regrets? I suspect one's choice in this case says a lot about one, and I also suspect that people like Atwood and Bezos would go for it: perhaps they would define "regret" as "not having tried something that could have been amazing!"
I read them as saying the same thing. What would Bezos be more likely to regret in the future - staying at a cushy high-paying job when he had an awesome idea he could have implemented, always wondering what might have been if only he had tried it, or trying a grand idea, failing at it, probably not losing much of anything, and going back to another cushy high-paying job?
Yes, in the case of Bezos, it was mostly his decision to leave his cushy, high-paying job to go start an online bookstore. It seemed crazy at the time, but he knew he would regret not trying.
