How to Think

Ever wonder why it's so hard to truly *think* in a world saturated with opinions? Alan Jacobs' *How to Think* offers a vital guide to navigating the complexities of our own minds and the influences that shape them. Through compelling stories like Megan Phelps-Roper's transformation and Leah Libresco's conversion, you'll uncover the hidden forces—attractions, repulsions, and the seductive power of words—that subtly dictate what we believe. Prepare to confront uncomfortable truths about our own biases and the human tendency to categorize. This book isn't about easy answers or simplistic open-mindedness; it's about cultivating intellectual flexibility, understanding the democratic spirit inherent in thoughtful communication, and embracing the inherent risks of genuine thinking. You'll gain a deeper awareness of how your mind works, learn to resist the urge to blindly follow the crowd, and discover the profound pleasures—and potential dangers—of forging your own intellectual path. Expect a journey that is both intellectually stimulating and emotionally resonant, challenging your assumptions and ultimately empowering you to think more critically and independently.

Alan Jacobs opens by recounting the story of Megan Phelps-Roper, formerly of Westboro Baptist Church, and her unlikely transformation sparked by interactions on Twitter. The author explains that Phelps-Roper's shift wasn't about suddenly thinking for herself, but about thinking *with* different people, revealing a core insight: thinking is inherently social. Jacobs challenges the notion of independent thought, suggesting it's both impossible and undesirable; every thought is a response to another. He critiques the common tendency to praise those who adopt views we agree with, while dismissing opposing views as the result of negative influences. Like Hansel and Gretel lured by a wicked witch, Jacobs notes. The author then dismantles another misconception: that rationality demands the suppression of feelings. He introduces John Stuart Mill, whose rigorous, feeling-starved upbringing led to a mental crisis. Mill's eventual embrace of poetry highlights the crucial role of feelings in a balanced intellect. Jacobs underscores that analysis alone isn't enough; character, cultivated through feeling, is essential for meaningful action. To illustrate the pitfalls of narrow rationality, Jacobs analyzes Malcolm Gladwell's critique of Wilt Chamberlain's free-throw shooting, arguing Gladwell overlooks Chamberlain's relational goals, namely, maintaining his desirability. This leads to the concept of relational goods—desires beyond mere economic or workplace success—which profoundly influence our decisions, like the communal values of Kansans that Thomas Frank overlooked. Jacobs argues these relational goods, though sometimes ethically dubious, are no less rational. He paints a picture of rationality not as cold calculation, but as a holistic engagement with the world, fueled by both thought and feeling. As Henry James wrote, it is about cultivating the “power to be finely aware and richly responsible”. Thus, Jacobs resolves that genuine thinking demands awareness, responsibility, and a recognition of our interconnectedness.

Alan Jacobs, in this chapter of *How to Think*, explores the subtle yet powerful forces that shape our beliefs and affiliations, opening with the story of Leah Libresco's conversion from atheism to Roman Catholicism through her engagement with the Yale Political Union. Jacobs highlights how Libresco's willingness to be "broken on the floor," to genuinely change her mind in debate, was a testament to the community's values and her trust in its members, revealing that our thinking is profoundly influenced by our social environment. He then introduces Jonathan Haidt's concept of moral intuitions that "bind and blind," suggesting that these intuitions, often formed before conscious reasoning, shape our moral matrices, but Jacobs pushes further, drawing on C.S. Lewis's idea of the Inner Ring to illustrate how the desire for belonging can insidiously corrupt our judgment, as the allure of acceptance often leads us to compromise our values. The chapter warns of the dangers of these exclusive circles, and Jacobs contrasts the unhealthy dynamics of the Inner Ring with the genuine community characterized by openness to questioning and thinking, using Lewis's concept of "Membership" to advocate for a fellowship where individuals are valued for their distinct contributions rather than forced into conformity. Like the diverse quartet in *The Wind in the Willows*, such communities foster true belonging, crucial for intellectual and personal growth. Jacobs then shifts to self-awareness, urging readers to assess their personal investments and motivations, questioning whether they are speaking their heart's truth or merely seeking to please, and he cautions against “unscrupulous optimism,” described by Roger Scruton, which prioritizes personal agendas over genuine understanding and negotiation. The chapter culminates with a reflection on the controversy surrounding Ta-Nehisi Coates's essay on reparations, where Jacobs argues that solidarity, while essential, should not overshadow critical reflection on the means to achieve desired ends, the chapter advocates for prudence, seeking allies, and maintaining a disposition toward kindness and generosity, recognizing that genuine fellowship often transcends shared beliefs and leads to intellectual and moral enrichment, emphasizing that the path to better thinking lies in understanding our attractions and cultivating genuine, open-hearted connections.

In this chapter, Alan Jacobs delves into the uncomfortable truth that our tolerance might not be as boundless as we believe, drawing heavily from Scott Alexander's concept of 'outgroups' to illustrate how easily we turn on those within our own circles who hold differing ideologies. Jacobs highlights Iyengar and Westwood's research, revealing that animosity toward these outgroups often outweighs loyalty to the ingroup, a chilling testament to our willingness to punish dissent. He uses the metaphor of academia and the church, communities he straddles, to showcase how the principle of 'the enemy of my enemy is my friend' can lead to ruthless alliances and the marginalization of opposing views. Jacobs cautions against the dangers of utopian optimism, where those who disagree are seen not just as wrong, but as active adversaries to be eliminated, echoing the sentiment that 'error has no rights.' He urges readers to commit to proceduralism, to uphold fair rules even when politically inconvenient, recognizing the seductive power of animus to cloud ethical and practical judgment. Jacobs then challenges us to confront our repulsions, acknowledging that while some ideas are genuinely repulsive, it's crucial to avoid 'Bulverism'—dismissing an opponent's argument by attributing it to some inherent flaw or pathology. Instead, he advocates seeking out the most thoughtful representatives of opposing viewpoints, even when our gut recoils. He cautions against the disinhibition fostered by modern communication technologies, which can turn neighbors into abstract 'Others,' making it easier to demonize them. Jacobs then critiques the notion of purely rational decision-making, dismantling Neil deGrasse Tyson's vision of 'Rationalia' by pointing to Antonio Damasio's research on the crucial role of emotions in sound judgment. He shares the story of SM, a woman without fear, to illustrate how biases, though imperfect, act as essential heuristics, guiding us through life's complexities. Ultimately, Jacobs argues that cultivating the right 'prejudices'—emotional predispositions—is vital for sound thinking, and that associating with the best people shapes our character and our ability to engage with opposing views charitably, like Megan Phelps-Roper's transformation. To strip away our emotional responses would be like removing the guardrails on a twisty mountain road, leaving us vulnerable to the madness of pure, unadulterated reason.

In this chapter of *How to Think*, Alan Jacobs, drawing from Thomas Hobbes, explores the seductive power of words and their potential to amplify both wisdom and foolishness. He begins by highlighting how literacy can enhance existing traits, for better or worse, and warns against treating words as true currency rather than mere counters. Jacobs then introduces Kenneth Burke's concept of "terministic screens," illustrating how language shapes our perceptions, directing our attention while simultaneously blinding us to other aspects. The deployment of keywords, Jacobs notes, often signals group affiliation, creating in-groups and out-groups through shared linguistic cues—a phenomenon he likens to prisoners numbering jokes, where the delivery matters as much as the content. He cautions that these keywords, while necessary for social cohesion, can become parasitic, displacing genuine thought, echoing George Orwell's concern about the reduction of consciousness through cliché. Jacobs then delves into the dangers of unacknowledged metaphors, particularly the pervasive "argument-as-war" metaphor, revealing how it fosters dichotomous thinking and dehumanizes interlocutors. To escape this trap, Jacobs urges us to recognize the myths we live by, as Mary Midgley suggests, patterns of thought that shape our interpretation of the world, often without our awareness—like the now common analogy between the brain and computer which encourages us to believe that we understand the brain better than we do. Jacobs then critiques the defensive strategy of "in-other-wordsing," where opponents' arguments are distorted or reduced to caricatures, and offers an alternative: the Long Now Foundation's debate format, where debaters must first summarize each other's arguments to their satisfaction. This approach, akin to method acting or dual booting, promotes empathy and understanding, creating an environment where genuine thinking can flourish, even if it means temporarily setting aside one's own convictions and facing the possibility of social discomfort. The path to wisdom, Jacobs suggests, requires demoting words from the money of fools to the counters of the wise, embracing the discomfort of nuanced thought over the ease of ideological conformity, and recognizing that true engagement demands a willingness to inhabit perspectives not our own, trading, even if momentarily, our native intellectual tongue for another.

Alan Jacobs, in "How to Think," delves into the human tendency to categorize, a process he calls "lumping," essential for managing the overwhelming influx of information. He draws a parallel to biological taxonomy, where lumpers group organisms into existing categories, contrasting with splitters who create new ones. This mirrors our daily lives, where we instinctively classify people and ideas, often relying on cognitive shortcuts like identifying in-groups and out-groups. Jacobs points out that our culture leans toward lumping, driven by the need for mental triage, especially evident in scenarios like college admissions or hospital emergency rooms where quick classifications—sometimes callous-seeming acronyms—become necessary for efficient decision-making. Yet, this lumping also serves a purpose of solidarity, illustrated by the evolution of the LGBTQIA+ movement, where diverse groups unite under a common banner of shared experience, fighting for fair and respectful treatment. However, such unity remains fragile, prone to internal divisions and external pressures. The author then invokes Orwell’s "Animal Farm" to highlight how easily categories can shift, revealing the underlying power dynamics at play. Jacobs emphasizes the importance of questioning who benefits from these classifications and who is victimized by them, viewing social taxonomies as temporary, provisional structures. The narrative shifts to John C. Calhoun, a passionate defender of slavery, to distinguish between those who passively accepted prevailing views and those who actively shaped and enforced harmful taxonomies. Finally, Jacobs champions the value of "splitting," advocating for skepticism toward categories and celebrating the eccentric individual who resists being defined solely by group membership. He invokes Terence’s line, "Homo sum, humani nihil a me alienum puto"—I am human, and nothing human is alien to me—as a guiding principle, urging us to recognize the dangers of strict separation and embrace the possibilities found in mutual understanding. Ultimately, Jacobs encourages us to let a billion eccentric individuals bloom, even those like Timothy, whose demon baby stories challenge our own habits of lumping.

Alan Jacobs, in this exploration of intellectual flexibility, begins by dismantling the simplistic notion of open-mindedness. He recounts the anecdote of John Maynard Keynes, who supposedly quipped about changing his mind when the facts change, as a common, often misattributed, ideal. However, Jacobs argues that unwavering open-mindedness is not only impossible but also undesirable; society requires settled convictions to progress. He draws on Chesterton's metaphor of the mind as a mouth, meant to be shut on something solid, emphasizing the need for discernment. The central tension arises: how do we balance conviction with adaptability? Jacobs suggests navigating between the vices of rigidity and flaccidity, seeking a virtuous middle ground, much like holding a bird—too tight, and you crush it; too loose, and it flies away. He introduces the concept of sunk costs, investments of time and energy that can irrationally bind us to failing ideas, illustrated by poker players who can't fold losing hands. Jacobs then recounts the fascinating case of Marian Keech and her religious cult, whose members escalated their commitment in the face of disproven prophecies, highlighting the human tendency to avoid intellectual bankruptcy even when reality crumbles. Drawing parallels to Charles Mackay's study of popular delusions, such as the South Sea Bubble, Jacobs cautions against the pervasive influence of intellectual sunk costs, even on those who study human error. He transitions to Eric Hoffer's analysis of "true believers"—those deeply invested in a single narrative, resistant to falsification. Jacobs underscores that while passionate beliefs are inevitable, an inability to imagine circumstances that would alter one's views signals the grip of sunk costs. Megan Phelps-Roper's escape from the Westboro Baptist Church serves as an example of overcoming such entrenchment, aided by the challenging voices of social media. Ultimately, Jacobs urges us to examine our own intellectual investments, to discern whether our convictions are prisons or foundations, and to cultivate environments where dissenting voices are not vilified but thoughtfully considered. As Lichtenberg wisely noted, a book is like a mirror; if a donkey looks in, one cannot expect an apostle to look out.

In this chapter from *How to Think*, Alan Jacobs, acting as our guide, delves into David Foster Wallace's insightful review of Bryan Garner's usage dictionary, revealing a profound connection between English usage and the Democratic Spirit. Wallace saw Garner's work as a model for persuasion without condescension, a rare feat of intellectual humility. Jacobs illuminates how Wallace's concept of the 'Democratic Spirit' hinges on the ability to hold passionate convictions while respecting the convictions of others, a balance as delicate as a perfectly balanced scale. The chapter explores the social challenges faced by 'SNOOTlets'—those precocious grammar enthusiasts—who struggle to navigate social codes, drawing a parallel between their linguistic isolation and a broader ethical failure to recognize and value diverse perspectives. Jacobs then navigates a sharp turn, examining the abortion debate as a crucible for testing our commitment to forbearance, that vital capacity to suppress our immediate, visceral reactions in favor of understanding. He underscores that the inability to code-switch, to engage with opposing viewpoints, tears at the social fabric. Jacobs suggests that humanizing those we disagree with—dismantling the 'Repugnant Cultural Other'—is crucial, even if unsettling, for intellectual growth. However, he cautions against relentless self-examination, noting its potential for misery, advocating instead for a balanced skepticism towards our own motives and a generosity towards others. Jacobs reframes Wallace's call for constant self-reflection, suggesting that brief, blunt introspection, akin to auricular confession, is more sustainable. Ultimately, the chapter resolves with the idea that cultivating this disposition of skeptical generosity is the 'royal road' to learning how to think, a journey marked by both intellectual rigor and emotional intelligence.

Alan Jacobs concludes his exploration of thinking by acknowledging the inherent risks alongside its profound rewards. He cautions that genuine thinking, which inevitably leads to changes in perspective, can strain social bonds, a painful prospect he doesn't dismiss with platitudes about ‘real friends.’ Instead, Jacobs advises a delicate approach: emphasizing shared beliefs, presenting new viewpoints with humility, and avoiding the fervor of a recent convert. He paints a vivid picture: imagine navigating a crowded room, each person a fixed point of view, and you, having shifted slightly, must now recalibrate your connections with care. Yet, Jacobs tempers this caution with a reminder that the pursuit of truth demands prioritizing it over social comfort, a value that requires courage. It’s not merely about technique, but about character, about being the kind of person who values truth. Thinking, he argues, isn't about arriving at a final destination but about embracing the journey itself, a continuous striving fueled by hope rather than paralyzed by despair or presumption. Like Victorian sages who sensed cracks in their own certainties, we too must embrace the excitement of intellectual exploration. Jacobs underscores that the benefits of thinking—gaining knowledge, deeper understanding, and personal growth—are well worth the effort, offering a hopeful vision for those willing to undertake this challenging yet ultimately enriching endeavor. Thinking, then, becomes not just an intellectual exercise, but a courageous act of self-creation.

Alan Jacobs' "How to Think" isn't a guide to logic puzzles, but a profound exploration of the social, emotional, and linguistic forces shaping our minds. The core takeaway is that thinking is fundamentally relational. We don't think in isolation; we think *with* and *against* others, influenced by attractions and repulsions, desires for belonging, and the subtle power of language. The book cautions against the illusion of independent thought, revealing how easily we mistake agreement with our own views for genuine intellectual autonomy. A key emotional lesson lies in recognizing the crucial role of feelings. Rationality isn't about suppressing emotions, but integrating them into our understanding. Cultivating healthy emotional predispositions, like kindness and generosity, is vital for sound judgment. Practically, the book urges intellectual humility: a willingness to be influenced, to examine our motivations, and to challenge our own settled convictions. It highlights the dangers of 'lumping,' the dehumanizing effect of categories, and the importance of celebrating individual eccentricity. Jacobs advocates for empathy and understanding, urging us to summarize opposing viewpoints and humanize those with whom we disagree. He emphasizes the need to balance solidarity with critical reflection, ensuring our commitments are informed by careful consideration. Ultimately, "How to Think" presents thinking as an ongoing journey, not a destination. It encourages us to avoid intellectual despair or presumption, remaining open to continuous learning and self-improvement. The book suggests that cultivating the character of someone who values truth is essential. The author suggests that we must be aware of the 'Inner Ring' dynamic, avoid Bulverism, practice prudence, and recognize the power of language as a 'terministic screen.' The health of our social environment for thinking is reflected in its attitude towards ideas from the outgroup. By embracing these principles, we can navigate the complexities of the modern world with greater wisdom, empathy, and understanding.