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jkaufman comments on Decision Auctions aka "How to fairly assign chores, or decide who gets the last cookie" - Less Wrong
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Alternatively it trains you to be more risk neutral.
I'm assuming that the individuals have divided their funds into "risk neutral" and "risk averse" in a discrete way, rather than with a continuous utility function. This makes sense when there's a clear discretionary / non-discretionary split; I can easily adjust my entertainment budget this month to compensate for losing $100, but I might not be able to easily adjust my rent budget to compensate for losing $1000.
If people don't have any funds they consider risk-neutral, then I think that doing some sort of gambling to develop the psychological skill of risk neutrality is important, but I doubt this is the optimal way to do that training.