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Having read Cicero's Academics, I'd like to learn a bit more about skepticism (through original texts, not summaries).

If a had to read only one book from Sextus Empiricus, would you recommend the Outlines on Pyrrhonism or Against the Mathematicians?

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I vote Outlines of Pyrrhonism. It provides an overview of disputes between Academics, Skeptics, and Dogmatists, presents an array of arguments of varying strengths for and against many common philosophical positions of the time, and triples as a playbook for how to be a Skeptic. For example, the variance in argument strength presented is by design, since as Sextus indicates, some people are ready to hear strong arguments, while some need to hear weaker arguments first.

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