In the first part of Chapter 5, Goodman considers some basic affinities of Emerson and Montaigne that are evident even before Emerson published “Montaigne, or the Skeptic”: their use of the essay form to register spontaneity and contingency, their critique of books and travel, their discussions of the play of moods, their attention to themselves. The second part of Chapter 5 considers the shape of Emerson’s Montaigne essay, which has its own moods and its own architecture, and which concludes by taking what the critic Barbara Packer calls “a miraculous act of levitation” outside the play of moods to the moral sentiment that “outweighs them all.” In evaluating this leap, Goodman deploys Emerson’s own skepticism against his more metaphysical and dogmatic tendencies. “Why so talkative in public,” he writes, “when each of my neighbors can pin me to my seat by arguments I cannot refute?”

Chapter 9 considers Emerson’s first revolutionary book of 1836, Nature. Even in this first book, Goodman argues, Emerson presents a nascent epistemology of moods. The discussion then turns to the moody swings of “Nature,” from the Essays, Second Series, in which Emerson finds the natural world either bountifully present or just missed, and as taking two opposing forms: a stable finished form he calls natura naturata, and a dynamic form he calls natura naturans. At the end of the essay, Emerson abandons this main set of oppositions in a leap to a metaphysical conclusion. The Coda considers Emerson’s attraction to Michael Faraday’s idea that “we do not arrive at last at atoms, but at spherules of force.”

Emerson describes a range of experiences that constitute friendship: titanic battles between beautiful enemies; conversational brilliance and expansion; a joyful solitude, as if someone has departed rather than arrived; a generalized benevolence toward people in the street to whom one does not speak; the warm sympathies and household joy one shares with a familiar friend; the disappointment of a friend outgrown. His account shows an intense focus on moral perfection – on our unattained but attainable self, alone and with others – but an equally intense awareness of what he calls in “Experience” “the plaint of tragedy” that sounds throughout our lives “in regard to persons, to friendship and love.” The chapter’s coda charts the opposition in “Love” between love as the experience of being “swept away” and a skeptical vision of marriage as a prison, from which sex, person, and partiality have vanished.

Chapter 4 begins by tracing some reappearances and interconnections of Emersonian themes, in what Goodman calls paths of coherence in Emerson’s philosophy: not a complete system, but ways that his thoughts hang together. The chapter focuses on “Nominalist and Realist,” where Emerson sets out the competing metaphysics of particulars and universals without reconciling their opposition. Near the end of the essay, he draws a skeptical lesson from his epistemology of moods. “I am always insincere,” he writes, “as always knowing there are other moods.” This might be cause for despair, but Emerson’s tone in this final paragraph is more in tune with ancient skepticism and Montaigne. He ends “Nominalist and Realist” by withdrawing from the dispute, but this does not mean that he gives up inquiring. Skepticism can be both a withholding of final judgment, and, as Herwig Friedl observes, “a constant looking around, without any attempt at closure.”

While it is important to trace Emerson’s main positions, one misses the living nature of his philosophy unless one also takes account of the motions, moods, and patterns within his essays, and the ways he dramatizes instability, spontaneity, and inconsistency. This emphasis is found in Goodman’s discussions of “History” in Chapter 1, “Friendship” in Chapter 3, “Nominalist and Realist” in Chapter 4, “Manners” in Chapter 6, “Experience” in Chapter 7, “Nature” in Chapter 9, and “Illusions” in Chapter 10. Chapter 2 distinguishes the sheer variety of skepticisms in Emerson’s thought, about the world and other minds, but also about mystical experiences that refuse “to be named” or are “ineffable.” It also attends to the differences between the “modern” tradition of skepticism as doubt, and skepticism as a form of life, with Emerson’s essay on Montaigne a key source for his idea of a “wise skepticism.”

Chapter 2 begins with Emerson’s responses to the ineffable character of mystical experience: one of silence and listening, the other of a profusion of terms from a multitude of cultures. Writings on mystical experience by William James and Ludwig Wittgenstein are part of the discussion. This chapter considers Emerson’s skepticism about the “external world” and “other minds” and about both freedom and fate, which form a “knot of nature.” The following section concerns skepticism as an existential condition, as when Emerson writes in “Experience”: “So it is with us, now skeptical, or without unity.” The chapter concludes by considering skepticism as a positive way of life, what Emerson calls a “wise skepticism.” This form of skepticism has roots in the ancient Greek and Roman worlds and, in a particularly important form for Emerson, in the Essays of Montaigne.

The Afterword recalls the importance of “emphatic experiences” throughout Emerson’s thought, especially in Nature, “The Over-Soul,” “Circles,” and “Spiritual Laws.” It also registers the many oppositions discussed in Emerson, the Philosopher of Oppositions: Reality and Illusion in “Experience,” “Unity” and “Variety,” “rest” and “motion,” in “Plato”; dead language and living poetry in “The Poet,” nominalism and realism in “Nominalist and Realist,” fate and freedom in “Fate.” Emerson “accepts” his “contrary tendencies” by building them into his essays, one after the other: “‘Your turn now, my turn next,’ is the rule of the game.” Skepticism pervades Emerson’s thought, as he registers doubts about knowledge, other minds, freedom, or meaning. But skepticism can also be understood as a way of life, as in ancient Greek philosophy and in Montaigne’s Essays, and Goodman argues for the attractions of Emerson’s own version of the skeptical life, what he calls a “wise skepticism.”

Chapter 1 examines the leading theory of chilling effects – chilling effects as fear of legal harm – a legalistic account most often employed by lawyers and judges in the United States, Canada, and beyond. The author explores its historical and intellectual origins, key actors that have articulated and influenced the theory, and argues this predominant conventional account is too narrow, legalistic, and deeply flawed theoretically and empirically, and cannot explain, predict, or understand chilling effects in a wide variety of contexts. As such, it only contributes to skepticism about chilling effects, rather than dispelling them.

Chapter 2 critically examines privacy-based conventional theories, which approach chilling effects as a result of privacy harms. While privacy-based theories of chilling effects improve on legal accounts, they are also too narrow and cannot explain chilling effects in a variety of contexts, including even forms of privacy-related chilling effects. Moreover, courts and judges have also remained deeply skeptical of privacy-based theories. To address these limitations and fully understand the threat chilling effects pose to freedom, fundamental rights, and democracy we need a new understanding of chilling effects that moves beyond conventional accounts.

This chapter introduces the concept of chilling effects and contextualizes it, both with historical and contemporary examples, including the chill of: recent state actions that are increasingly authoritarian; online surveillance in the Snowden leaks; big data collection in the Cambridge Analytica scandal; automated surveillance in Clearview AI; as well as the modern origins of the chilling effects concept. The author also discusses persistent skepticism about chilling effects by lawyers, judges, scholars, and researchers, and why, and provides an outline of the conformity theory advanced in the book. The author ends with a road map for the structure of the book.

The chapter explores in the nature of the act of the will Kant analyses in Groundwork I and II. I argue that Kant provides us with a metaphysical – and not phenomenological – analysis of what it means to have a will. The phenomenological analysis is subject to skeptical challenges. His argument is based on what follows when we take ourselves as having a will, something that we do every time we act. This analysis reveals that the act of willing immediately implies a subjection to the moral law. This act of the will is identical to the fact of reason with which Kant begins his second Critique. I show this through a closer look at what follows when we take the will as negatively free, that is, as not determined in the order of causes. I argue that Kant held that when we examine the essence of the will, it follows that any act of willing that is negatively free must also have a law of its activity, one supplied by reason, for the idea of an undetermined will contains a contradiction (6:35). Hence any act of the will must embody both negative and positive freedom. This means further that Kant is an internalist about reasons for moral action.

This chapter provides a short overview of the secondary literature concerning this problem, in particular both “reversal” and “deflationary” readings of Kant’s project. It introduces the basic strategy of the argument of the book, namely that Kant’s analysis in the first part of Groundwork III does not move from the conditions of thinking to freedom of the will, but rather from the conditions of willing to the conditions of thinking: The “I will” implies the “I think” and as such all of the conditions of thinking. Several possible objections are refuted at the outset in order to provide a clear context for the chapters that follow, and the content of each of the following chapters is summarized.

This chapter presents summary of the conclusions reached in the book.