 From the point of view of the ancient skeptics, assertions are expressions of dogmatism. And yet, the best-known ancient skeptic, Sextus Empiricus, wrote extensively. Can the skeptics say anything meaningful about their philosophy without asserting anything about how things are (Bett 2013, 2019)? Skeptical writings have a peculiar format, one that comes with its own challenges: the skeptics aim to describe their philosophy tout court, as they practice it, without laying out any particular theories or doctrines. Skeptical ideas have been charged with a family of objections: they might be self-refuting, inconsistent, self-contradictory, and so on (Castagnoli 2010). Another line of objection is associated with Hume, namely that “nature is always too strong for principle.” As Hume puts it, “a Pyrrhonian cannot expect that his philosophy will have any constant influence on the mind” (part 2 of section 12, “Of the Academical or Sceptical Philosophy,” An Enquiry Concerning Human Understanding, London, 1748). It is one thing for skepticism to be coherent. It is another thing for it to be likely that anyone, no matter how much they rehearse skeptical arguments in their mind, will succeed in adhering to it (Johnson 2001), as ancient Pyrrhonist philosophers claimed to be able to do.