I think "Rationality is winning" is a bit of a trap. 

(The original phrase is notably "rationality is systematized winning", which is better, but it tends to slide into the abbreviated form, and both forms aren't that great IMO)

It was coined to counteract one set of failure modes - there were people who were straw vulcans, who thought rituals-of-logic were important without noticing when they were getting in the way of their real goals. And, also, there outside critics who'd complain about straw-vulcan-ish actions, and treat that as a knockdown argument against "rationality."

"Rationalist should win" is a countermeme that tells both groups of people "Straw vulcanism is not The Way. If you find yourself overthinking things in counterproductive ways, you are not doing rationality, even if it seems elegant or 'reasonable' in some sense."

It's true that rationalists should win. But I think it's not correspondingly true that "rationality" is the study of winning, full stop. There are lots of ways to win. Sometimes the way you win is by copying what your neighbors are doing, and working hard. 

There is rationality involved in sifting through the various practices people suggest to you, and figuring out which ones work best. But, the specific skill of "sifting out the good from the bad" isn't always the best approach. It might take years to become good at it, and it's not obvious that those years of getting good at it will pay off.

Source:
https://www.lesswrong.com/posts/3GSRhtrs2adzpXcbY/rationality-winning

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