10 Thought-Provoking Books Like Freakonomics

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Fifteen years after its initial publication, Freakonomics remains one of the most influential books about economic theory ever written. That’s because it uses economics as a starting point, then jumps into several unexpected and atypical applications of its tenets. From an analysis of how Japanese sumo wrestlers collude to the controversial conclusion that legalized abortion resulted in lower crime rates, Steven Levitt and Stephen J. Dubner continue to set the bar by examining academic or scientific subjects through a pop culture lens.

If you’ve read Freakonomics and you’re inspired to keep looking at the world from unexpected perspectives, fear not—there are plenty of books that will scratch the same itch. From economics to psychology to history, each of the books listed here takes a complicated subject and examines it using a combination of anecdote, humor, and lateral thinking. Whether your goal is to be the smartest person at your next cocktail party or to simply develop new perspectives, these 10 books like Freakonomics will uncover new facets of the world.

1. SuperFreakonomics, by Steven Levitt and Stephen J. Dubner

If Freakonomics is your jam, the obvious choice for a follow-up is the official sequel. Dubner and Levitt once again apply economic theory to a variety of unexpected situations ranging from prostitution in Chicago to the infamous 1964 murder of Kitty Genovese in New York City. The conclusions drawn from these unusual studies are as surprising and thought-provoking as in the original; in one example, they conclude that the wages of Chicago sex workers are limited by the presence of women who are perfectly willing to engage in sexual intercourse for free.

Levitt and Dubner don’t mess with a successful formula. They bring plenty of humor and energy to their writing and aren’t afraid to make controversial statements (some of their conclusions regarding climate change caused quite a stir). The sequel got slightly less attention simply because the novelty was gone, but it sports the same unconventional approach not just to economics, but to life itself.

2. An Economist Walks into a Brothel, by Allison Schrager

Another book that takes economic theory—which author Allison Schrager defines as ”buying and selling risk”—and applies it outside the world of finance. An Economist Walks into a Brothel has a narrower focus than Freakonomics, but is no less entertaining or informative. Schrager argues that risk is more pervasive than most people believe. We all take risks on a daily basis, and one of the first lessons of the book is that we should start recognizing these risks, which can be as basic as deciding to take the bus instead of driving to work because we think it will be faster.

Schrager then demonstrates how to use risk management tools to be more strategic about the risks we take. She delves into hedging risk by examining the economics of the music industry, lowering risk through diversification via the world of horse racing, and how to quantify risk through an entertaining romp through Hollywood. The central lesson here—that we should all think about risk and acquire the skills to manage it—is one that could have an immediate impact on your life.

3. Fooled by Randomness, by Nassim Taleb

If there’s a unifying theme to the books on this list, it’s that human beings go through life crippled by their assumptions, and the most powerful thing you can do is challenge those assumptions. Nassim Taleb, a statistician who has established himself as the leading expert on risk and uncertainty, offers a compelling argument that human beings are almost totally wrong in how they view random chance in Fooled by Randomness. He makes the case that we incorrectly believe that everything can be explained, attribute causality when chance is the more obvious explanation, and are easily fooled by the counter-intuitive nature of odds.

It’s very different in style and approach from Freakonomics, but Taleb writes in a clear, straightforward manner, and the book offers a similar lesson in forcing yourself to see the world from a different perspective using economic theory. For example, Taleb argues that we over-value winners, overlooking the fact that they are usually outliers. We seek to emulate those who emerge triumphant, but the more important lessons are usually found in the much more common experience of losing. That’s precisely the sort of outside-the-box thinking fans of Freakonomics will appreciate.

4. Outliers, by Malcolm Gladwell

There’s a tendency to assume that those who rise to the top of their field must be inherently gifted with some sort of preternatural ability. Whether it’s a musician with a string of platinum albums or a tech genius unveiling their latest life-altering product, genius is often viewed as a form of magic—some people are just born with a specific something that makes them better than everyone else.

Malcolm Gladwell’s Outliers accepts that talent or genius is necessary to be incredibly successful, but argues that we don’t put enough stock in simple luck and the benefits of circumstance. This argument takes us in some unexpected directions; Gladwell points out that the economic depressions of the 1830s and 1930s not only offered future tycoons a fertile economic situation but also resulted in a beneficial educational surplus of fewer students and more over-qualified teachers. The idea that successful people have systemic advantages, or that some people are simply lucky, isn’t new or particularly surprising, but Gladwell exposes how often we discount it. Success thus becomes a concrete result of data points instead of a mystical, mysterious event.

5. Influence: The Psychology of Persuasion, by Robert Cialdini

We’d all like to think that we’re in charge of our existence, but Robert Cialdini argues that we are constantly being manipulated. This manipulation comes in the form of marketing and design, following basic principles of human psychology. Learning what those principles are and being able to see them in action will change how you view just about every interaction in your life.

Cialdini demonstrates these principles with simple, real-life thought experiments. In one, he talks about the power of commitment—the compulsion people have to follow through on an action they have agreed to, even if that agreement was symbolic or manipulated. For example, when people are asked by a stranger to watch their belongings on a public beach, they follow through on this commitment. Psychologically, the same principle is at work when people add items to an Amazon Wish List: They have, in a sense, committed to purchasing the item and are thus much more likely to eventually buy it. This book reveals how web sites, politicians, and even the layout and design of physical stores engage powerful psychological trickery to alter our behavior, and that seeing the trick is half the battle.

6. Thinking, Fast and Slow, by Daniel Kahneman

Every one of our decisions is the result of thought in one sense or another—either the “fast” thought of intuition and reaction or the “slow” thought of contemplation and analysis. Despite the fundamental importance of our thought processes, few of us have a clear understanding of how they work, or how they could be improved. Psychologist Daniel Kahneman examines the science of thought and concludes that despite our love of gut instincts and snap decisions, our “intuitive” thought systems are unreliable and inaccurate. At the same time, slow thinking requires energy and time, while fast thinking is easy and satisfying, which leads us to overvalue the latter and undervalue the former.

Kahneman uses statistics to demonstrate many of his conclusions, but he avoids getting too deep into the weeds, keeping the vocabulary clear and direct. Changing how we view our thought processes isn’t just about personal improvement. Kahneman shows how the different ways we think—and the different levels of accuracy and reliability from the fast and the slow—have real-world implications that affect all of us.

7. Dataclysm, by Christian Rudder

You hear the term “big data” a lot, and most of us have at least some conception of what that means. But few have as clear an understanding as Christian Rudder, who founded the dating site OkCupid. Rudder lives and breathes data, and his examination of big data and the revelations it offers about us as a population in Dataclysm is both eye-opening and worrying. One thing is certain: The age of Big Data is upon us, and we can no longer live our lives assuming that we have anything approaching true privacy.

But Big Data can also offer unexpected truths. Rudder explores how easy it can be to figure out details about your life from a relatively small number of data points. He then goes on to extract some chilling lessons about modern Americans, including how shockingly racist we remain as a society—and how uniquely racist we are compared to other countries. If you think the data Google and Facebook scoop up about you is only used to sell you corporate America’s wretched things, this book will disabuse you of the notion: Everything today is data, and understanding how it will be used is essential.

8. Capital in the Twenty-First Century, by Thomas Piketty

Although Thomas Piketty’s remarkably popular economics book isn’t as general as Freakonomics and is grounded in much more traditional economic theory, it’s still a startlingly revolutionary work. Piketty doesn’t view wealth as inherently destructive, but he does make the argument that the way returns on investments outpace economic growth dooms advanced economies to gross inequity. He then makes the case that this is exactly what’s happened in the United States, where the mega-wealthy have managed to protect themselves from taxes and other instruments for redistributing that wealth.

If Freakonomics inspired you to look at the world in new and unusual ways, Capital in the Twenty-First Century will clarify how money actually works in the world, and why the global movement of wealth affects you even if you’re not obsessed with getting more of it.

9. The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life, by Mark Manson

Mark Manson’s eminently readable tirade against the self-help industry is a book that, like Freakonomics, offers a counter-intuitive lens through which to view the world. Manson argues that most self-help books and programs are little more than ego-stroking, encouraging you to see yourself as strong and powerful without actually helping you to solve any of your problems. That in turn traps you in a cycle of constantly seeking new self-help guides to keep pumping yourself up with all the “progress” you’re making.

Manson thinks a better approach is to acknowledge problems and try to solve them, not just feel better about them. As you progress through Manson’s blunt and sometimes profane advice, a lot of our assumptions about self-help and personal development are attacked and proved wrong. For example, where many self-help gurus preach maintaining a positive attitude, Manson points out that research shows forcing positivity increases stress. The healthier option is to experience your negative feelings and thoughts so you can deal with them.

10. Thinking in Bets, by Annie Duke

World Series poker champion Annie Duke knows a lot about betting and playing odds and thinks many aspects of our lives would benefit from viewing them as bets. This shift in how you view the world is transformative; after all, there are many scenarios where you might have incomplete information, but you can still make an educated assessment. You can, in other words, make a bet. We make many bets in our everyday lives, so knowing more about the art and science behind them can only benefit us.

Thinking in Bets explores some of the cognitive biases that blunt our ability to calculate bets and make better decisions, like our tendency to conflate success with correct assumptions instead of luck, or seeking evidence to support our assumptions while deprecating evidence that does otherwise. These are the sort of eye-opening revelations that can change how you approach problems and opportunities going forward in your life.

About Author

Jeff Somers ( was born in Jersey City, New Jersey and regrets nothing. He is the author of nine novels, a book on the craft of writing, and numerous short stories. His guitar playing is a plague upon his household and his lovely wife The Duchess is convinced he would die if left to his own devices.

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