It seems like there's really just one base Umeshism: "If you have not encountered adverse consequences, you have sunk too much value into mitigating risk."

I don't agree with this general form in all possible permutations; it could be instantiated as "If you've never been killed by a car, you've spent too much time looking both ways", and there doesn't seem to be a distinction contained in the structure that separates that example and other, less obviously wrong instantiations.

Perhaps the appropriate lesson is "If you are investing in avoiding adverse consequences, but have never suffered them, consider that you may be sacrificing too much for the sake of risk aversion." A general instruction to update in a particular direction on the proper balance between risk aversion and reward seeking, but not an absolute. However, in order to believe that, I'd like to see some evidence that the modal member of the target audience is actually overestimating the risks they want to avoid to such a degree that advice to indiscriminately avoid risk less would actually be helpful.

I think I need one example of a meta-Umeshism.