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Eliezer_Yudkowsky comments on Test Your Rationality - Less Wrong
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The thought occurs to me that the converse question of "How do you know you're rational?" is "Why do you care whether you have the property 'rationality'?" It's not unbound - we hope - so for every occasion when you might be tempted to wonder how rational you are, there should be some kind of performable task that relates to your 'rational'-ness. What kind of test could reflect this 'rationality' should be suggested from consideration of the related task. Or conversely, we ask directly what associates to the task.
Prediction markets would be suggested by the task of trying to predict future variables; and then conversely we can ask, "If someone makes money on a prediction market, what else are they likely to be good at?"
I think there is likely a distinction between being rational at games and rational at life. In my experience those who are rational in one way are very often not rational in the other. I think it highly unlikely that there is a strong correlation between "good at prediction markets" or "good at poker" and "good at life". Do we think the best poker players are good models for rational existence? I don't think I do and I don't even think THEY do.
A suggestion:
List your goals. Then give the goals deadlines along with probabilities of success and estimated utility (with some kind of metric, not necessarily numerical). At each deadline, tally whether or not the goal is completed and give an estimation or the utility.
From this information you can take at least three things. 1. Whether or not you can accurately predict your ability. 2. Whether or not you are picking the right goals (lower than expected utility would be bad, I think) 3. With enough date points your could determine your ration of success to utility. Too much success and not enough utility means you need to aim higher. Too little success for goals with high predicted utility mean either aim lower or figure out what you're doing wrong in pursuing the goals. If both are high you're living rationally, if both are low YOU'RE DOING IT WRONG.
The process could probably be improved if it was done transparently and cooperatively. Others looking on would help prevent you from cheating yourself.
Not terribly rigorous, but thats the idea.
I'm not sure if this works, since a lazy person could score very low on utility yet still be quite rational.