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Qiaochu_Yuan comments on Rationality Quotes July 2013 - Less Wrong
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This advice really only applies in contexts where the risks of failure substantially outweigh the rewards of success. This isn't true in many contexts; if they're approximately equally balanced, it makes sense to attempt to work slightly above your level of competence in order to improve your skill, and if the rewards of success substantially outweigh the risks of failure it makes sense to be even more risk-loving.
I think that you may have misunderstood the point that I was trying to make. I am not advocating excessive caution. Rather, I value self-knowledge and knowledge of the environment and the people you interact with in that environment. Obviously, a certain amount of margin of error should be included in any decision making.
It has been my experience as a driving instructor that most pupils are entirely too cautious especially on faster roads where going too slowly may cause a following vehicle to attempt an unsafe overtaking manoeuvre