Jiro comments on Median utility rather than mean? - Less Wrong Discussion
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If your preferences aren't transitive, then even your one-shot decision making system is completely broken, since it can't even yield an action that is "preferred" in a meaningful sense. Vulnerability to money pumping would be the last of your concerns in this case.
Money pumping is an issue in sequential decision making with time-discounting and/or time horizons: any method to aggregate future utilities other than exponential discounting ( * ) over an infinite time horizon yields dynamic inconsistency which could, in principle, be exploited for money pumping.
The intuitive justification for the independence axiom is the following:
This decision making example looks intuitively irrational. If you prefer ice cream to cake when they are the only two alternatives, then why would you prefer cake to ice cream when a third, inferior, alternative is included? The independence axiom formalizes this intuition about rational behavior.
( * with no discounting being a special case of exponential discounting)
It can be rational to do this. There's a paradox publicized by Martin Gardner demonstrating how. Unfortunately the best link I could easily find was a Reddit comment, but try https://www.reddit.com/r/fffffffuuuuuuuuuuuu/comments/gxwqe/why_i_hate_people/c1r5203 .