9 books that will change how you think about thinking.

Books that would break a lot of myths, clarify a couple of misconceptions, and would force you to look at things differently.

Abhishek Chakraborty
Mar 11 · 15 min read

The best books are those which hit you in the head with bricks, and reconfigure your entire understanding of reality, people, life, and even yourself.

These 9 books would break a lot of myths, clarify a couple of misconceptions, and most likely would force you to look at things differently.

If you look at things differently from the other person, you are already half way ahead. Let these books guide you.

1. Thinking, Fast and Slow

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What it’s about:

Daniel Kahneman is a Nobel prize-winning psychologist and possibly one of the most influential academics and thinkers in the past 50 years. Kahneman, along with his colleague Amos Tversky, are the godfathers of Behavioural Economics.

Thinking, Fast or Slow is a layman’s summary of their entire body of work. Kahneman takes us on a tour of the mind and explains the two systems that drive the way we think. System 1 is fast, intuitive, and emotional; System 2 is slower, deliberative, and logical.

Notable quotes:

“A reliable way to make people believe in falsehoods is frequent repetition, because familiarity is not easily distinguished from truth. Authoritarian institutions and marketers have always known this fact.”

“Intelligence is not only the ability to reason; it is also the ability to find relevant material in memory and to deploy attention when needed.”

“The idea that the future is unpredictable is undermined every day by the ease with which the past is explained.”

Why you should read it:

If you are even remotely interested in behavioural economics, this book is for you. It is an astonishingly rich book, full of intellectual surprises and self-help value. It is consistently entertaining and frequently touching, especially when Kahneman is recounting his collaboration with Tversky, his late friend and colleague, who would have definitely shared the Noble with Kahneman, had he lived. This book will rearrange the way you think about how you think. This book will help you know who you really are — from a scientific point of view.

Kahneman is so unassuming and humble that you can’t but enjoy his writing. This is the best self-help book one might ever need to read, mainly because it is really not a self-help book, and hence has zero BS.

You’ll realise the dozens of ways your brain sucks. You’ll be a little bit less sure of yourself, a little bit more aware of your own biases and mental shortcuts, and a little more sceptical of all the BS being thrown your way — by other books and other people.

2. The Black Swan

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What it’s about:

In this book, Nassim Nicholas Taleb introduces the concept of the Black Swan. A black swan is a highly improbable event with three principal characteristics: It is unpredictable; it carries a massive impact; and, after the fact, we concoct an explanation that makes it appear less random, and more predictable, than it was.

Notable quotes:

“Missing a train is only painful if you run after it! Likewise, not matching the idea of success others expect from you is only painful if that’s what you are seeking.”

“When you develop your opinions on the basis of weak evidence, you will have difficulty interpreting subsequent information that contradicts these opinions, even if this new information is obviously more accurate.”

“The problem with experts is that they do not know what they do not know.”

Why you should read it:

If you generally do not like reading books, and want to read only one book squeezing everything from psychology, statistics, life and human behaviour into one book, this is most probably the one to go ahead with.

Many people have written against Taleb’s tone of writing, but I admire him. When he scorns others, there is disgrace which makes his rare praises all the more believable.

Taleb’s writing reflects a true passion and dedication to the beliefs he expounds in the book — beliefs that are drawn from his own observations and experiences as a risk analyst, and worthy of all your attention. In life and in business, we deal with uncertainty all the time, this book is a good way to understand what that really means.

The Black Swan glides through deep philosophical discussions and clever humour as effortlessly as its namesake. You are likely to be deeply enthralled by Nassim Nicholas Taleb’s erudition and wisdom concerning the philosophy of uncertainty.

As Bertrand Russell had famously said, “The good life is one inspired by love and guided by knowledge.” This is real, practical, and the most brutal kind of knowledge.

3. Zen and The Art of Motorcycle Maintenance

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What it’s about:

This book is a powerfully moving & penetrating examination of how we live, and a breathtaking meditation on how to live better. Robert M. Pirsig addresses the question, “What is best?” while motorcycling with his son on a cross-country trip.

Notable quotes:

“If someone’s ungrateful and you tell him he’s ungrateful, okay, you’ve called him a name. You haven’t solved anything.”

“You look at where you’re going and where you are and it never makes sense, but then you look back at where you’ve been and a pattern seems to emerge.”

“Sometimes it’s a little better to travel than to arrive”

Why you should read it:

Robert Pirsig’s genius in Zen and the Art of Motorcycle Maintenance is to insert classical forms of thought into the backdrop of a cross-country motorcycle trip. As a Chautauqua, this book is in a league of its own. As an exploratory bit of writing on a bike trip across the country, it has more weight than a mere philosophical writing.

Pirsig talks about good design, peace of mind, the value of the right education, his pursuit of quality, human psychology, and a lot about how to maintain your motorcycle. Most of his ideas are presented as subtext, and hence doesn’t come off as a sermon. It reads like someone’s diary.

He essentially tries to break down the ways people make value judgments and how they reason. At the centre of this is how we view and react to aspects of technology. He splits it up into the classic (function) and the romantic (form) — all while narrating his trip with his son.

This is the kind of a book which needs more than a dozen readings. There is always something new to discover in the subtexts. Read it with patience — you’ll definitely enjoy it.

4. Algorithms to Live By

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What it’s about:

In a dazzlingly interdisciplinary work, acclaimed author Brian Christian and cognitive scientist Tom Griffiths show how the algorithms used by computers can also untangle very human questions. They explain how to have better hunches, when to leave things to chance, how to deal with overwhelming choices, and how best to connect with others.

This book is a fascinating exploration of how insights from computer algorithms can be applied to our everyday lives, helping to solve common decision-making problems and illuminate the workings of the human mind

Notable quotes:

“Some of the biggest challenges faced by computers and human minds alike: how to manage finite space, finite time, limited attention, unknown unknowns, incomplete information, and an unforeseeable future; how to do so with grace and confidence; and how to do so in a community with others who are all simultaneously trying to do the same.”

“Even the best strategy sometimes yields bad results — which is why computer scientists take care to distinguish between “process” and “outcome.” If you followed the best possible process, then you’ve done all you can, and you shouldn’t blame yourself if things didn’t go your way.”

“The greater the uncertainty, the bigger the gap between what you can measure and what matters, the more you should watch out for overfitting — that is, the more you should prefer simplicity”

Why you should read it:

This book beautifully combines computer science, psychology, behavioural and applied economics, statistics and several other fields into one compelling and insightful book.

Algorithms to Live By is full of rich examples, and doesn’t bog the reader down with mathematical detail. I found it fascinating that actively using algorithms while making every day decisions will not only reduce stress, it will genuinely make us happier and free up more time to do productive things. Read it to make smarter decisions.

5. How Not to Be Wrong

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What it’s about:

The maths we learn in school can seem like a dull set of rules, laid down by the ancients, not to be questioned. In this book, Jordan Ellenberg shows us how terribly limiting this view is: Maths isn’t confined to abstract incidents that never occur in real life, but rather touches everything we do — the whole world is shot through with it.

Notable quotes:

“I think we need more math majors who don’t become mathematicians. More math major doctors, more math major high school teachers, more math major CEOs, more math major senators. But we won’t get there unless we dump the stereotype that math is only worthwhile for kid geniuses.”

“A basic rule of mathematical life: if the universe hands you a hard problem, try to solve an easier one instead, and hope the simple version is close enough to the original problem that the universe doesn’t object.”

“Knowing mathematics is like wearing a pair of X-ray specs that reveal hidden structures underneath the messy and chaotic surface of the world.”

Why you should read it:

How Not to Be Wrong is to Mathematics what The Design of Everyday Things is to Design. Like DOET, after reading it you don’t get to become a mathematician of course, but you learn enough to generate curiosity about the subject and start thinking of having a closer look at this fascinating field. You would wish mathematics was taught this way while you were in school— as an applied science.

Ellenberg shows that the boring certainty people associate with maths is often misplaced. A big chunk of mathematics is actually devoted to uncertainty, and that’s where things are really interesting. This book is also an excellent guide to the many ways our biased intuitions and poorly understood statistical training can lead us astray, especially in times of uncertainty.

This book takes us behind the numbers, equations, theories and abstruse concepts to show the practical applications of whatever we have been taught. Along the way, the history of these various ideas are explained with various anecdotes — which are both informative and amusing.

This is a smart, fun read. I highly recommend this book to all people who are even vaguely interested in maths, probability, logic, and their application in everyday life.

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6. Superforecasting

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What it’s about:

We all are terrible forecasters. In this book, Philip Tetlock and Dan Gardner explore if some people do have real foresight. And if they do, what makes them so good in it, and can these skills be learnt by others as well?

Notable quotes:

“It is wise to take admissions of uncertainty seriously,” Daniel Kahneman noted, “but declarations of high confidence mainly tell you that an individual has constructed a coherent story in his mind, not necessarily that the story is true.”

“For superforecasters, beliefs are hypotheses to be tested, not treasures to be guarded.”

“Consensus is not always good; disagreement not always bad. If you do happen to agree, don’t take that agreement — in itself — as proof that you are right. Never stop doubting.”

Why you should read it:

Written in an engaging and accessible style, Superforecasting illustrates every concept with a good story, often featuring national surprises like 9/11 and the lack of WMDs in Iraq with explanations of why forecasters missed what looks obvious in hindsight.

Ultimately, this is a book about critical thinking that challenges the reader to bring more rigour to his or her own thought processes. Tetlock and Gardner have made a valuable contribution to a world of internet factoids and snap judgments.

You might think there isn’t much need for accurate forecasting in your profession or personal life. But as you progress with this book, you’ll learn a lot of interesting things that would genuinely surprise you. Very insightful book not only on forecasting, but also on leadership, organisation, politics, etc.

7. Zero to One

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What it’s about:

Peter Thiel explores the relationship between technology, society, and historical moments in this unique book of business philosophy. The book is both about how to start a company and how to save the world: entrepreneurship as business and entrepreneurship as social salvation.

Notable quotes:

“EVERY MOMENT IN BUSINESS happens only once. The next Bill Gates will not build an operating system. The next Larry Page or Sergey Brin won’t make a search engine. And the next Mark Zuckerberg won’t create a social network. If you are copying these guys, you aren’t learning from them.”

“EVERY ONE OF TODAY’S most famous and familiar ideas was once unknown and unsuspected.”

“The single greatest danger for a founder is to become so certain of his own myth that he loses his mind. But an equally insidious danger for every business is to lose all sense of myth and mistake disenchantment for wisdom.”

Why you should read it:

The best thing about the book is that it explains everything from a meta level. It doesn’t present a formula or a framework to follow (as done in books like The Lean Startup). It presents a school of thought, a philosophy, an idea. You have to read this more than once. The more you read, the more you would get to uncover the layers.

This book doesn’t talk as much about building a startup or a company, as much as it talks about building the future — with the right mindset. What sets it apart from the others is that it amalgamates Economics, Philosophy, and Innovation while talking about entrepreneurship.

8. The Design of Everyday Things

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What it’s about:

Even the smartest among us can feel inept as we fail to figure out which light switch or oven burner to turn on, or whether to push, pull, or slide a door. The fault, argues this ingenious — even liberating — book, lies not in ourselves, but in product design that ignores the needs of users and the principles of cognitive psychology.

In this entertaining and insightful analysis, cognitive scientist Donald A. Norman hails excellence of design as the most important key to regaining the competitive edge in influencing consumer behaviour.

Notable quotes:

“Design is really an act of communication, which means having a deep understanding of the person with whom the designer is communicating.”

“Good design is actually a lot harder to notice than poor design, in part because good designs fit our needs so well that the design is invisible, serving us without drawing attention to itself. Bad design, on the other hand, screams out its inadequacies, making itself very noticeable.”

“A brilliant solution to the wrong problem can be worse than no solution at all: solve the correct problem.”

Why you should read it:

Anyone who designs anything to be used by humans — from physical objects to computer programs to conceptual tools — must read this book, and it is an equally tremendous read for anyone who has to use anything created by another human.

Have you ever stood in front of a door, or a microwave, absolutely flummoxed, because the damned thing gave you no clue whatsoever how to open it. If so, you will enjoy this book. If not, then also you would equally enjoy it.

Norman would point out the obvious things you take for granted, and would make you think about them in an entirely new light. He breaks down the simplest devices into their basic functions & features, then rebuilds them in a way that is both obvious and yet entirely new.

He then points out places where the design elements are good & bad. He gets into the basic aspects of design that you never considered. Best of all, he lays all of this out in an interesting manner with common examples that are easy to follow even for a non-designer — as he delves deeper into the problems and solutions.

After reading this you will never look at any man-made object the same. You will question everything from doors to tea kettles to the most sophisticated computer program. The next time you fumble with an answering machine, web page, or light switch you will think back to the lessons from this book. It is almost liberating once you can see beyond the design of everyday things.

It is an absolutely must read if you are in a position to create something — anything from a software, a chair, or even a door knob.

9. Fooled by Randomness

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What it’s about:

This book is mostly about luck, or more precisely, how you deal with it in life and in business. It is a captivating insight into one of the least understood factors of all our lives.

Notable quotes:

“Heroes are heroes because they are heroic in behavior, not because they won or lost.”

“Probability is not a mere computation of odds on the dice or more complicated variants; it is the acceptance of the lack of certainty in our knowledge and the development of methods for dealing with our ignorance.”

“No matter how sophisticated our choices, how good we are at dominating the odds, randomness will have the last word.”

Why you should read it:

If you are even remotely interested in Philosophy, Statistics, Behavioural Economics, Psychology and Mathematics, this book acts as a great starting point.

One of the constant themes that you’ll find particularly interesting are about the hindsight bias and the narrative fallacy. We humans are great at fabricating post hoc narratives about our world. It’s how we understand (and misunderstand) the world.

This book will also most likely make you a bit more humble. It will reveal how much you don’t actually know. Many of the greatest qualities you assume about yourself are likely deluded or, at best, the result of a streak of luck.

This book might make you more comfortable with failure, and persuade you to not let success get inside your head since you might not really have earned all of that just by hard work.

10. Bonus: Creativity, Inc

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What it’s about:

Ed Catmull, the co-founder of Pixar Animation Studios distils down what it takes to manage a creative company. This is also a history of Pixar, and the story behind their much loved movies.

Notable quotes:

“If you give a good idea to a mediocre team, they will screw it up. If you give a mediocre idea to a brilliant team, they will either fix it or throw it away and come up with something better.”

“Failure isn’t a necessary evil. In fact, it isn’t evil at all. It is a necessary consequence of doing something new.”

“You are not your idea, and if you identify too closely with your ideas, you will take offence when they are challenged.”

Why you should read it:

This book would give you a practical framework that you can put to use in your company/team from today itself. In this process, it would bust a couple of well known myths about team management and leadership as well.

Ed Catmull explains what is creativity, and how you can foster it in an organisation. You don’t get feel-good abstract ideas from him, or cherry picked solutions to the most commonest of problems. Instead, you get an approach to tackle problems that you face in any creative organisation. Mostly, you get a good starting point. “The future is not a destination — it is a direction,” Ed Catmull makes his point very clear.

This is a book for managers who want to lead their employees to new heights, a manual for anyone who strives for originality, and the first-ever, all-access trip into the nerve centre of Pixar Animation — into their meetings, postmortems, and “Braintrust” sessions where some of the most successful films in history are made.

About the author:

Hi, I’m Abhishek. I’ve written 50+ essays which have been featured and quoted in Lifehacker, Psychology Today, ACM Digital Library, Springer, and Interaction Design Foundation.

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Notes on making better decisions, persuading others, and getting things done.

Abhishek Chakraborty

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I write about practical life skills to help you live in a world you do not fully understand:


Notes on making better decisions, persuading others, and getting things done.