Why am I passionate about this?

I’m an author, tech philosopher, father, geek, pianist, and novelist; and I'm fascinated by what it means to think clearly and well. Our world is bristling with complexities and crises; with staggering technologies, opportunities, and threats. What does it mean to find some kind of clarity, focus, and community amid this maelstrom? How can we hope to grasp, together, the nature of our times? These are the questions that keep me up at night—and that have driven me to write books that, I hope, can help and support people in rigorously exploring such questions for themselves.


I wrote

How to Think: Your Essential Guide to Clear, Critical Thought

By Tom Chatfield,

Book cover of How to Think: Your Essential Guide to Clear, Critical Thought

What is my book about?

This is my third book about critical thinking. I wrote it during the early days of the pandemic and wanted…

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

The books I picked & why

Book cover of What Is Philosophy For?

Tom Chatfield Why did I love this book?

Mary Midgley was in her nineties when she wrote this book, yet it’s alive with ideas and energy – and the insistence that philosophy should be “for” something in the most urgent, practical sense; that it should help us explore such questions as to how to live and to do good. Midgley was both highly scientifically literate and fiercely opposed to the claim that science will ever answer every question. We humans, she believed, are brilliant animals who need to understand our biological heritage as richly as possible if we’re to grapple fruitfully with our planetary future. I can think of few more urgent themes for the present century.

By Mary Midgley,

Why should I read it?

1 author picked What Is Philosophy For? as one of their favorite books, and they share why you should read it.

What is this book about?

Why should anybody take an interest in philosophy? Is it just another detailed study like metallurgy? Or is it similar to history, literature and even religion: a study meant to do some personal good and influence our lives?


In her last published work, Mary Midgley addresses provocative questions, interrogating the various forms of our current intellectual anxieties and confusions and how we might deal with them. In doing so, she provides a robust, yet not uncritical, defence of philosophy and the life of the mind.

This defence is expertly placed in the context of contemporary debates about science, religion, and…


Book cover of Invisible Women: Data Bias in a World Designed for Men

Tom Chatfield Why did I love this book?

One of the most important aspects of critical thinking is identifying and questioning faulty assumptions, and Invisible Women is one of the most brilliant recent examples I’ve seen of this in action. Criado Perez offers a rich and meticulously researched account of the ways in which women’s experiences, bodies, needs, and histories have been systematically effaced in countless settings; how, for example, the “normal” human measurements used to design everything from car safety features to phone handsets are based on male rather than female bodies. This is a devastatingly eye-opening book and a call to action against complacency of all kinds.

By Caroline Criado Perez,

Why should I read it?

13 authors picked Invisible Women as one of their favorite books, and they share why you should read it.

What is this book about?

Winner of the 2019 Financial Times and McKinsey Business Book of the Year Award
Winner of the 2019 Royal Society Science Book Prize

Data is fundamental to the modern world. From economic development, to healthcare, to education and public policy, we rely on numbers to allocate resources and make crucial decisions. But because so much data fails to take into account gender, because it treats men as the default and women as atypical, bias and discrimination are baked into our systems. And women pay tremendous costs for this bias, in time, money, and often with their lives.

Celebrated feminist advocate…


Book cover of Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets

Tom Chatfield Why did I love this book?

Taleb has written a handful of wonderful books exploring the ways in which human beings tend to systematically misunderstand the world. This was his first, and it’s a fantastic place to begin. As the title suggests, he’s fascinated by the ways in which chance events can seem significant when, in fact, this significance is merely an illusion; how, for example, we can’t resist seeing events in terms of cause and effect even when this is wishful nonsense. Taleb is a risk expert and mathematician – but he’s also a dazzling explainer and fearless provocateur, drawing on history and personal experience to bring statistically rigorous ways of thinking to life. 

By Nassim Nicholas Taleb,

Why should I read it?

6 authors picked Fooled by Randomness as one of their favorite books, and they share why you should read it.

What is this book about?

Everyone wants to succeed in life. But what causes some of us to be more successful than others? Is it really down to skill and strategy - or something altogether more unpredictable?

This book is the bestselling sensation that will change the way you think about business and the world. It is all about luck: more precisely, how we perceive luck in our personal and professional experiences. Nowhere is this more obvious than in the markets - we hear an entrepreneur has 'vision' or a trader is 'talented', but all too often their performance is down to chance rather than…


Book cover of Teaching Critical Thinking: Practical Wisdom

Tom Chatfield Why did I love this book?

This is a slim, passionate, personal book by one of the most significant American educators and activists of the last century. It’s part of her “teaching” trilogy (the other two books cover Community and Freedom) and is founded on the belief that “one could choose to educate for the practice of freedom.” Critical thinking is often treated as an emotionless, logical discipline, but this book shows how it’s rooted in a deep human longing for understanding—and is also vital to informed, equitable democratic participation. Teaching Critical Thinking is a profound testament to the significance of emotionally, politically, and intellectually engaged pedagogy – and why these three things are ultimately inseparable. 

By bell hooks,

Why should I read it?

1 author picked Teaching Critical Thinking as one of their favorite books, and they share why you should read it.

What is this book about?

In Teaching Critical Thinking, renowned cultural critic and progressive educator bell hooks addresses some of the most compelling issues facing teachers in and out of the classroom today.

In a series of short, accessible, and enlightening essays, hooks explores the confounding and sometimes controversial topics that teachers and students have urged her to address since the publication of the previous best-selling volumes in her Teaching series, Teaching to Transgress and Teaching Community. The issues are varied and broad, from whether meaningful teaching can take place in a large classroom setting to confronting issues of self-esteem. One professor, for example, asked…


Book cover of Thinking, Fast and Slow

Tom Chatfield Why did I love this book?

This might be the most famous book written in recent years about thinking – and the ways in which we’re all astonishingly vulnerable to various kinds of bias, distortion, and selectivity in our views of the world. But it’s also a book that offers hope in the sheer care with which it synthesizes a lifetime of thought and research. To be human is to be hasty, flawed, and partial; but it’s also to be part of an ongoing collective negotiation with these limitations. This is a foundational text for embarking upon that negotiation, and one that Nobel laureate Kahneman has put together with a careful mix of clarity and wisdom.

By Daniel Kahneman,

Why should I read it?

45 authors picked Thinking, Fast and Slow as one of their favorite books, and they share why you should read it.

What is this book about?

The phenomenal international bestseller - 2 million copies sold - that will change the way you make decisions

'A lifetime's worth of wisdom' Steven D. Levitt, co-author of Freakonomics
'There have been many good books on human rationality and irrationality, but only one masterpiece. That masterpiece is Thinking, Fast and Slow' Financial Times

Why is there more chance we'll believe something if it's in a bold type face? Why are judges more likely to deny parole before lunch? Why do we assume a good-looking person will be more competent? The answer lies in the two ways we make choices: fast,…


Explore my book 😀

How to Think: Your Essential Guide to Clear, Critical Thought

By Tom Chatfield,

Book cover of How to Think: Your Essential Guide to Clear, Critical Thought

What is my book about?

This is my third book about critical thinking. I wrote it during the early days of the pandemic and wanted to capture the ways in which critical thinking skills can help us in the face of escalating uncertainties and crises. How thinking well is rooted in honest doubt, collaboration, and empathy just as much as in reading, research, and logic. This result is a slim, personal book that—I hope!—invites you to explore what the lifelong journey of thinking more richly about thinking itself might look like for you.

You might also like...

Uniting the States of America: A Self-Care Plan for a Wounded Nation

By Lyle Greenfield,

Book cover of Uniting the States of America: A Self-Care Plan for a Wounded Nation

Lyle Greenfield Author Of Uniting the States of America: A Self-Care Plan for a Wounded Nation

New book alert!

Why am I passionate about this?

I’ve always been fascinated by group dynamics, large and small. Why things functioned well, why they didn’t. It’s possible my ability to empathize and use humor as a consensus-builder is the reason I was elected president of a homeowners association, a music production association, and even an agricultural group. Books were not particularly involved in this fascination! But in recent years, experiencing the breakdown of civility and trust in our political and cultural discourse, I’ve taken a more analytical view of the dynamics. These books, in their very different ways, have taught me lessons about life, understanding those with different beliefs, and finding ways to connect and move forward. 

Lyle's book list on restoring your belief in human possibility

What is my book about?

We’ve all experienced the overwhelming level of political and social divisiveness in our country. This invisible “virus” of negativity is, in part, the result of the name-calling and heated rhetoric that has become commonplace among commentators and elected leaders alike. 

My book provides a clear perspective on the historical and modern-day causes of our nation's divisive state. It then proposes easy-to-understand solutions—an action plan for our elected leaders and citizens as well. Rather than a scholarly treatment of a complex topic, the book challenges us to take the obvious steps required of those living in a free democracy. And it…

Uniting the States of America: A Self-Care Plan for a Wounded Nation

By Lyle Greenfield,

What is this book about?

Lyle Greenfield's "Uniting the States of America―A Self-Care Plan for a Wounded Nation" is a work of nonfiction and opinion. Incorporating the lessons of history and the ideas and wisdom of many, it is intended as both an educational resource and a call-to-action for citizens concerned about the politically and culturally divided state of our Union. A situation that has raised alarm for the very future of our democracy.

First, the book clearly identifies the causes of what has become a national crisis of belief in and love for our country. How the divisiveness and hostility rampant in our political…


5 book lists we think you will like!

Interested in decision making, teaching methodss, and metaphysics?

Decision Making 88 books
Metaphysics 102 books