MichaelVassar comments on Less Wrong Rationality and Mainstream Philosophy - Less Wrong
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It's true that Quine lacked the insights of contemporary probability theory and AI, but remember that Quine's most significant work was done before 1970. Quine was also a behaviorist. He was wrong about many things.
My point was that both Quine and Yudkowsky think that recursive justification bottoms out in using the lens that sees its own flaws to figure out how humans gain knowledge, and correcting mistakes that come in. That's naturalized epistemology right there. Epistemology as cognitive science. Of course, naturalized epistemology has made a lot of progress since then thanks to the work of Kahneman and Tversky and Pearl and so on - the people that Yudkowsky learned from.
Who cares when his work was done. We want to know how to find work that helps us to understand things today. It's not about how smart he was, but about how much his ideas can help us.
And my answer is "not much." Like I say, all the basics of Quinean philosophy are already assumed by Less Wrong. I don't recommend anyone read Quine. It's (some of) the stuff his followers have done in the last 30 years that is useful - both stuff that is already being used by SIAI people, and stuff that is useful but (previously) undiscovered by SIAI people. I listed some of that stuff here.