John_Maxwell_IV comments on POSITION: Design and Write Rationality Curriculum - Less Wrong
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Martial arts masters and psychotherapy gurus could say the same. Instead of sunk costs you could teach newbies to notice post-colonial alienation or intelligent design, and sure enough they'd get better at noticing that thing in their lives. I hear scientologists do lots of exercises too. Maybe creating exercises before measures is a positive expected value decision, but I wouldn't bet on that.
To the extent that irrationality is a result of compartmentalization, this may be the same thing as creating a way to measure how effectively you are accomplishing your goals, which is going to vary between people depending on what their goals are.
For most interesting goals I can think of, creating a rigorous quantitative measure is next to impossible. However, there are a few goals, like running a mile in under four minutes, that lend themselves well to this approach. Perhaps SI could find a group of individuals engaged in such a goal and offer their services as rationality consultants?