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Zubon comments on How has lesswrong changed your life? - Less Wrong
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Any particular approach you would like to cite there? I've found Peirce's pragmatic maxim to be a good shorthand for a lot of that. "This is just word games with bad definitions."
http://wiki.lesswrong.com/wiki/The_map_is_not_the_territory is very important.
It's also very helpful training to look at various paradoxes such as the Liar Paradox, The Unexpected Hanging Paradox, the Raven Paradox and so on.