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JoshuaZ comments on Dark Arts: Schopenhauer wrote The Book on How To Troll - Less Wrong
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Some of these which are labeled as bad aren't necessarily. For example, getting someone to accept a bunch of premises and then pointing out the conclusion is one way you can actually get people to change their opinions. I know I've had my opinion changed that way. Similarly, the use of Black Swan is questionable- one person might see something as a Black Swan where another will see it as a basic counterexample that needs to be dealt with. The dividing line is not at all clear.
I did say the "checkmate" methods were the most legitimate. This is "Hoy To Be Always Right", not "How To Always Be A Demagogical Sophist": the parts that involve manipulating the opponent without actually resorting to lies and fallacies are the most satisfying, since those are the parts where it's more clearly "intellect vs intellect", and the parts where you actually know yourself to be right. A clean fight is a good fight. As for Black Swans, they are obviously subjective in that they depend on how well-informed the receiving party is. Usually we talk about Black Swans when it's the enitre scientific community that's taken aback by a paradigm breaker.