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This chapter considers the following thesis and its supporting argument. Philosophical Skepticism: There is no way we could ever attain full philosophical understanding of our knowledge. The Radical Argument: (A1) Any theory of knowledge must be internalist or externalist. (A2) A fully general internalist theory is impossible. (A3) A fully general externalist theory is impossible. (C) Therefore, philosophical skepticism is true. It argues that there is no good reason to yield to the skeptic or to reject externalist theories of knowledge globally and antecedently as theories that could not possibly give us the kind of understanding of human knowledge in general that is a goal of epistemology. And so there is no good reason to accept philosophical skepticism, the main target thesis of this chapter.

This chapter discusses philosophical skepticism as a concept that critiques human problems of finitude. This skepticism is a particularly virulent form of a more general epistemic rationalism. By the twenty-first century, it ramified into a scientism that divided the world into an all-or-nothing of certain (rational) knowledge, and total uncertainty or relativism. The chapter particularly examines the work of Stanley Cavell who challenged dominant models of rationalism by linking the mind and the world through concepts derived from the study of language. It presents Cavell's discussions of skepticism about minds and about the existence of the external world as the secular appearances of the struggle against human finitude.

This chapter juxtaposes Friedrich Hölderlin's use of poetic language with his view in philosophical skepticism. Hölderlin used poetry to mediate between the antinomies of mind and world, as well as the nature and freedom. He reiterated that this mediation can only be articulated in poetic language. However, although his poetry aims to link the contradiction of many subjects, he does not believe in the “truth of skepticism”—the recognition that human subjects inevitably strive to have certainty (whether about the world, other minds, or the divine) that they cannot possess, and that this dissatisfaction with the uncertain state of one's knowledge is a constitutive of human subjectivity. Studying these two contradicting themes, the chapter explains how his poetry demonstrates the boundaries between language, mind, and world.

This chapter offers an interpretation of David Hume's body of work as simultaneously sensitive to how uncertainty and risk can enervate commercial actors and committed to emboldening these actors to take more risks. Hume's writings on passion, cognition, politics, and commerce reveal an apt representation of how risk and uncertainty are entangled in the minds of subjects, as well as a robust explanation for why so many people are made anxious by risks, even ones that promise a good outcome. Hume's expressions of philosophical skepticism and his treatment of probability establish his view that deep uncertainty is the background condition for commerce and for the politics of commercial societies, and show that he is unusually mindful of the disconcerting experience of living with uncertainty.

Chapter 7 introduces a distinctive idea of default assumptions and explains how that idea reconfigures earlier virtue epistemology. Default assumptions are endemic to human performance domains generally including games and sports. Our domains of judgment are only special cases in which a telic normativity allows performers to assume by default the standing of the background conditions required for success and aptness of performance. This enables a fresh treatment of philosophical skepticism. The response to the skeptics will be that they have mistaken what is required for the epistemic quality of ordinary judgments and beliefs. This treatment of skepticism is enabled by analogies between epistemic and athletic performance, and between episteme and praxis more generally.