A Review of How to Think by Alan Jacobs: A Survival Guide for a World at Odds

In a world overrun with hot takes, comment wars, and lightning-fast judgments, How to Think: A Survival Guide for a World at Odds by Alan Jacobs offers a rare and refreshing invitation: slow down, reflect, and learn how to really think—not just react. It’s not a traditional self-help book with tidy steps and bullet points. Instead, it’s a philosophical and practical exploration of why thinking is hard—and how we can do it better.

Thinking Isn’t Natural—Belonging Is

Jacobs begins with a paradox: while we like to believe we’re rational individuals, our brains are wired more for belonging than for reasoning. As Jacobs puts it, “The fundamental problem we have may be best described as not wanting to think.” He illustrates this with the example of David Foster Wallace’s famous parable of two young fish who don’t know what water is—they’re so immersed in it, they don’t realize it surrounds and shapes them. Similarly, we’re all swimming in the currents of groupthink, confirmation bias, and social signaling without realizing it.

Jacobs unpacks this through real-world examples—like the media frenzy over Justine Sacco, a woman who tweeted a poorly worded joke before boarding a flight to Africa and found her life dismantled by the time she landed. The lesson isn’t whether her tweet was right or wrong—it’s how quickly a public (and moral) consensus forms in the age of Twitter, and how eagerly people sign on for a digital stoning. It’s a chilling reminder of how easy it is to think with the mob.

Thinking Takes Courage—and Practice

Jacobs draws heavily on thinkers like C.S. Lewis and George Orwell to make his case that genuine thought is courageous and countercultural. One striking example comes from Frederick Douglass, the great abolitionist who was once criticized by his fellow activists for dialoguing with those who supported slavery. Douglass believed that engaging with his ideological opponents was not a betrayal, but a strategic and moral necessity. He didn’t just speak to the choir—he made his case to his adversaries, modeling a kind of intellectual bravery that’s all too rare today.

That, Jacobs says, is real thinking: not “us versus them,” but a sincere exploration of “What might they see that I’m missing?” It’s not agreement he’s calling for—it’s the willingness to open the door to another perspective, to risk complexity.

Thinking Requires Empathy

One of the book’s most compelling ideas is that thinking is fundamentally moral. It requires empathy and humility. Jacobs introduces the idea of the "Repugnant Cultural Other"—those people we instinctively dismiss or disdain. He challenges us to resist the urge to caricature them, and instead, to exercise “the charitable imagination”: the effort to understand why someone might hold a view you dislike.

This isn’t the same as agreeing, and Jacobs is clear about that. But until we understand the logic and context of a differing view, we haven’t really earned the right to dismiss it. One practical tool Jacobs offers is the “Rapoport Rules,” drawn from psychologist Anatol Rapoport and later championed by Daniel Dennett. These rules encourage us to summarize the other person’s argument so clearly and fairly that they say, “Yes, that’s what I mean.”

Why How to Think Matters Now

In our polarized age—politically, socially, even within families—Jacobs’ book isn’t just a guide to better personal thinking. It’s a civic call to arms. He doesn’t promise that careful thinking will make you popular or even always right. But it will make you more thoughtful, more compassionate, and less easily manipulated.

How to Think is a deceptively simple book—short, conversational, and unassuming—but its implications are profound. It doesn’t offer easy answers. Instead, it gives readers the tools to ask better questions. In a world shouting for attention, Jacobs invites us to the quieter, braver work of listening, reflecting, and thinking deeply.

If you're tired of the noise and yearning for clarity—not just in politics or culture, but in everyday life—this book is an essential read. Not because it tells you what to think, but because it teaches you how.

Find the book here