40 Books that Improve your Ability to Make Decisions

Who can you ask for book recommendations on decision making? At Re:Think Decision Making, I asked a crowd that one former ivy league professor called “the best public crowd he’s ever seen” what they would recommend reading. These people are paid to make decisions for a living and want to find every edge they can.

So when I asked them what books on decision making influenced them, you can bet they had a lot to say.

Here’s the list in no particular order:

1. Decisive: How to Make Better Choices in Life and Work

By: Chip & Dan Heath

Research has shown time and time again how irrational humans are in our thinking. We’re overconfident. We seek out information that supports us and downplay information that doesn’t. We get distracted by short-term emotions. When it comes to making choices, it seems, our brains are flawed instruments. Unfortunately, merely being aware of these shortcomings doesn’t fix the problem, any more than knowing that we are nearsighted helps us to see.

Well researched and well written, this book offers a 4 step process to help overcome our natural biases and make better decisions. On a side, if you’ve read Switch or Made to Stick you know how fun and easy a Heath brothers book is to read. This one is no different.

2. How to Measure Anything

By: Douglas Hubbard

Peter Drucker famously said, “What gets measured, gets managed.” But how do you measure things as nebulous as customer satisfaction, organizational flexibility or the ROI of technology?

Written by recognized expert Douglas Hubbard—creator of Applied Information Economics—How to Measure Anything illustrates how the author has used his approach across various industries and how any problem, no matter how difficult, ill defined, or uncertain can lend itself to measurement (and therefore improvement) using proven methods.

3. How to Make Sense of Any Mess: Information Architecture for Everybody

By: Abby Covert

According to the author, every “mess” has a similar structure. Whether we’re dealing with a crisis at work or at home, find ourselves in a muck with other people, or are trying to make sense of the deluge of information all around us, this book offers a 7 step process for making sense of it all. No mess is too big once you know how to properly tackle one.

4. Wiser: Getting Beyond Groupthink to Make Groups Smarter

By: Cass Sunstein & Reid Hastie

If you work with groups of people in any way, this is a great read with lots of useful nuggets. We tend to assume that a group of bright minds working together to solve a problem would yield the best outcome, but research has shown that isn’t always the case. In fact, we tend to sabotage our own results by giving the most weight to the positions stated first, shared the loudest, or held in common with the rest of the group. In Wiser, you’ll not only learn how to avoid the pitfalls that plague so many meetings today, but how to get the best out of those participating, so your collective decision making becomes more effective, more productive, and a better investment of time.

5. The Surprising Power of Liberating Structures: Simple Rules to Unleash A Culture of Innovation

By: Henri Lipmanowicz & Keith McCandless

Whether you are a teacher, a manager, a parent, or a leader in any way, you know how frustrating it can be when the individuals you’re trying to lead aren’t fully engaged. It’s bad for the organization, it’s bad for productivity, and quite frankly, it’s bad for the individual. The Surprising Power of Liberating Structures explores practical methods to help people get engaged and invested in what they’re doing — and feel personal satisfaction from doing it.

6. Gamestorming: A Playbook for Innovators, Rulebreakers, and Changemakers

By: Dave Gray, Sunni Brown & James Macanufo

If your work environment isn’t one where employees feel safe to share their ideas and interact freely with one another, you can’t expect to accomplish anything significant. You’ll always be chugging along at less than full capacity. That’s where this book comes in. It provides over 80 games that are specifically designed to break down barriers, foster communication, and get the creative juices flowing.

7. The Righteous Mind: Why Good People are Divided by Politics and Religion

By: Jonathan Haidt

Think you’re absolutely right on the hot political, social or religious debate of the day? Before you get into it with your brother-in-law over Thanksgiving dinner, make sure you read this book. Jonathan Haidt does a masterful job of showing that the other side isn’t as crazy as we think, and in fact, we’re all a bit more crazy than we’d like to admit. He draws on decades of research to show that what we consider to be moral judgments are not formed by sound reasoning, but by intuition. Understanding why and how that happens is critical to understanding each other. And a necessary part of having an opinion.

8. Yes or No: The Guide to Better Decisions

By: Spencer Johnson

Who Moved My Cheese? gets a lot of love, but Spencer Johnson’s book on decision making deserves way more attention than it gets. In my opinion, it’s his best book. And it’s short, practical and easy to apply. You could read this over your lunch break and be a better thinker before you even finish your sandwich.

9. The Little Book of Talent

By: Daniel Coyle

This is a great companion piece to the Talent Code by the same author, but definitely stands on its own. Where that book is more about the science and research behind developing talent, The Little Book of Talent gives you the “how to” with over 50 specific exercises you can start using today to improve whatever skill you’re working on — whether it’s art, music, sports, or cooking eggs. This book will help you get better, faster.

10. The Worry Solution: Using Breakthrough Brain Science to Turn Stress and Anxiety into Confidence and Happiness

By: Martin Rossman

Seneca once said, “He who suffers before it is necessary suffers more than is necessary.” Often, that unnecessary suffering comes from excessive worrying. I get it, there’s plenty to worry about today — kids, finances, your career, relationships — the list is endless. This book offers practical and actionable steps to get worry under control, so it stops adding unnecessary stress and anxiety to your life.

11. Shantaram: A Novel

By: Gregory David Roberts

One of the only novels on the list, Shantaram is less of a book on how to make decisions, but rather a fascinating case study on how the direction of our life is inextricably tied to the decisions we make. At nearly 1000 pages, this is not an afternoon read, but it is a thrilling ride that doesn’t slow down once it starts rolling. From the inside cover:

Shantaram is narrated by Lin, an escaped convict with a false passport who flees maximum security prison in Australia for the teeming streets of a city where he can disappear. Burning slums and five-star hotels, romantic love and prison agonies, criminal wars and Bollywood films, spiritual gurus and mujahideen guerrillas—this huge novel has the world of human experience in its reach, and a passionate love for India at its heart. Based on the life of the author, it is by any measure the debut of an extraordinary voice in literature.

12. The Art of Living

By: Epictetus

One of the most influential Stoic thinkers, Epictetus was born into slavery about 55 ce in the eastern outreaches of the Roman Empire. Once freed, he established a school of Stoic philosophy, stressing that human beings cannot control life, only their responses to it. By putting into practice the ninety-three witty, wise, and razor-sharp instructions that make up The Art of Living, you’ll learn to meet the challenges of everyday life successfully and to face life’s inevitable losses and disappointments with grace.

13. The Education of a Value Investor

By: Guy Spier

This book packs a lot into its pages. It’s both a priceless education in value investing, and a riveting story of personal transformation. Among other valuable lessons, you’ll discover how a $600,000+ lunch with Warren Buffet turned out to be one of the best (and high yielding) investments author Guy Spier ever made.

14. Devil Take the Hindmost: a History of Financial Speculation

By: Edward Chancellor

Before you drop a dime into that hot tech stock your co-worker is raving about, pick up this book. The author takes a hard look at both the psychological and economic forces that drive people to “bet” their money in markets; how markets are made, unmade, manipulated; and who wins when speculation runs rampant.

15. Click: The Art and Science of Getting from Impasse to Insight

By: Eve Grodnitzky

Wouldn’t it be nice if we could be inspired on demand? Get a fresh jolt of energy, insights and creativity when we’ve hit the wall? According to author Eve Grodnitsky, we can. In Click, she provides a 7 step methodology to take someone from “impasse to insight.” Drawing on the latest research and her own analysis of hundreds of real-life insight stories, Dr. Grodnitzky explains how insight actually works and how to have more of these eureka moments at work and in life.

16. The Dictator’s Handbook: Why Bad Behavior is Almost Always Good Politics

By: Bruce Bueno de Mesquita

The authors of this book make a bold claim: leaders do whatever keeps them in power, regardless of the national interest. And while there are clear differences between a liberal democracy and a dictatorship, the common thread through both is the same — scratch the right backs, and keep the people in the dark. This is an entertaining, yet at times unsettling, manual for gaining and preserving power — akin to Machiavelli’s The Prince.

17. The Back of the Napkin & How to Solve Problems and Sell Ideas

By: Dan Roan

Have you ever had a hard time expressing a complex idea to someone? In this book, author Dan Roan suggests using fewer words and more pictures. He shows how a few simple drawings done the right way can clarify any problem or sell any idea to your audience — whether that’s one person or a full auditorium.

18. Crossing to Safety

By: Wallace Stegner

One of only three novels on the list. From the inside flap:

Called a “magnificently crafted story . . . brimming with wisdom” by Howard Frank Mosher in The Washington Post Book World, Crossing to Safety has, since its publication in 1987, established itself as one of the greatest and most cherished American novels of the twentieth century. Tracing the lives, loves, and aspirations of two couples who move between Vermont and Wisconsin, it is a work of quiet majesty, deep compassion, and powerful insight into the alchemy of friendship and marriage.

19. Paradox of Choice: Why More is Less

By: Barry Schwartz

No matter what you’re in the market for, you have options. Lots of them. Where to invest your money, how to order your coffee, what to wear, and don’t even get me started on the menu at the Cheesecake Factory.

In Paradox of Choice, Schwartz makes the counter intuitive case that too many options can actually be a bad thing — and eliminating choices can reduce the stress, anxiety, and busyness of our lives. He offers 11 practical steps to limit choices to a manageable number, have the discipline to focus on the ones that are important, and derive greater satisfaction from the choices you have to make.

20. Streetlights and Shadows: Searching for the Keys to Adaptive Decision Making

By: Gary Klein

When making an important decision, should you go with your gut or lean more on logic and statistics? The answer may not be as clear cut as you’d expect, and each situation requires its own approach. In Streetlights and Shadows, Gary Klein debunks the conventional wisdom about how to make decisions. He takes ten commonly accepted claims about decision making and shows that they are better suited for the laboratory than for life — and what we should do instead.

21. The Social Animal

By: David Brooks

The Social Animal weaves the narrative of a fictional American couple (from birth to old age) with the most recent research on social and cognitive science to illustrate how we develop during different stages of our lives. Brooks paints a new and refreshing view of humanity and what it really means to be successful.

22. The Laws of Simplicity

By: John Maeda

In this short but engaging read, graphic designer and computer scientist Maeda proposes ten laws for simplifying complex systems in business and life (but mostly focuses on product design.) Maeda’s upbeat explanations break down the power of less — fewer features, fewer buttons and fewer distractions — while providing practical strategies for harnessing that power.

23. Nudge: Improving Decisions about Health, Wealth and Happiness

By: Richard H. Thaler

By now, it shouldn’t surprise you to learn that humans are inherently bad at making decisions. And only through understanding and being aware of our biases can we ever hope to get better at it. This is a well written and easy to read book, written by Richard Thaler (who happens to be a Nobel Prize winner.) If you want to improve your own decision making, and also learn how to “nudge” those you care about towards making better choices as well, grab this book.

24. Reminiscences of a Stock Operator

By: Edwin Lefevre & Roger Lowenstein

First published in 1923, Reminiscences of a Stock Operator is perhaps the most widely read, highly recommended investment book ever. And after nearly 100 years on the shelves, it’s just as relevant today as it was when it was first written. Generations of readers have found that it has more to teach them about markets and people than years of hands-on experience.

25. This Will Make You Smarter

By: John Brockman

“What scientific concept would improve everybody’s cognitive toolkit?”

This is the question John Brockman posed to the world’s most influential thinkers. This book is a collection of their answers. Daniel Kahneman, Nassim Nicholas Taleb, Richard Dawkins, Brian Eno, Steven Pinker, Lisa Randall — the list goes on and on. You’ll definitely pick up something new and immediately useful in this book.

26. A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas

By: Warren Berger

In A More Beautiful Question, Warren Berger makes the compelling argument that our outcomes are directly tied to the quality of questions we’re willing to ask. By showing how to approach questioning with an open, curious mind and a willingness to work through a series of “Why,” “What if,” and “How” queries, Berger offers an inspiring framework of how we can all arrive at better solutions, fresh possibilities, and greater success in business and life.

Pairs nicely with this podcast interview. ;)

27. Red Notice: A True Story of High Finance, Murder, and One Man’s Fight for Justice

By: Bill Browden

I’ve talked about this book before and it remains high on my personal recommendation list. It’s hard to believe this story recounts actual events — it reads just like a fictional crime thriller and was difficult for me to put down. If you’re into conspiracies, crime, and politics — run for office. Just kidding, get this book.

28. The Man who Mistook his Wife for a Hat

By: Oliver Sacks

This book is a collection of some of the most bizarre, fascinating, and at times heartbreaking stories of people afflicted with a variety of neurological disorders. We learn about patients who are no longer able to recognize people and common objects; who are stricken with violent tics and grimaces or who shout involuntary obscenities; whose limbs have become alien; and who have been dismissed as retarded yet are gifted with uncanny artistic or mathematical talents.

29. Imprudent King: A New Life of Philip II

By: Geoffrey Parker

Philip II is not only the most famous king in Spanish history, but one of the most famous monarchs in English history: the man who married Mary Tudor and later launched the Spanish Armada against her sister Elizabeth I.

This book examines Philip’s long apprenticeship; his three principal interests (work, play, and religion); and the major political, military, and personal challenges he faced during his long reign. Parker offers fresh insights into the causes of Philip’s leadership failures: was his empire simply too big to manage, or would a monarch with different talents and temperament have fared better?

30. Seeking Wisdom

By: Peter Bevelin

Inspired by the wisdom of Charlie Munger, Seeking Wisdom is a compendium of the big ideas that shape the way we see and interact with the world. This book is one of my personal favorites and has had a massive impact on how I think and view reality. (Get it.)

31. Mastery

By: Robert Greene

Robert Greene insists that we all have it within us to be masters. And in Mastery, he provides the formula. The same formula that was used by great historical figures such as Charles Darwin, Mozart, Paul Graham and Henry Ford.

32. Synchronicity: The Innes Path of Leadership

By: Joseph Jaworski

“Synchronicity” is the term used to describe the feeling that everything in life — the ups, the downs, the disasters and the triumphs, seem to work together for your good. Author Joseph Jaworski argues that the right state of mind will make you the kind of person who can enlist the cooperation of fate and take advantage of synchronicity, creating the conditions for “predictable miracles.”

33. The Culture Map: Breaking Through the Invisible Boundaries of Global Business

By: Erin Meyer

Americans precede anything negative with three nice comments; French, Dutch, Israelis, and Germans get straight to the point; Latin Americans and Asians are steeped in hierarchy; Scandinavians think the best boss is just one of the crowd. It’s no surprise that when they try and talk to each other, chaos breaks out. This is the book to help you navigate those tricky and potentially awkward misunderstandings.

34. Ubiquity: Why Catastrophes Happen

By: Mark Buchanan

Critically acclaimed science journalist, Mark Buchanan tells the fascinating story of the discovery that there is a natural structure of instability woven into the fabric of our world, which explains why catastrophes — both natural and human — happen.

35. Family Fortunes

By: Bill Bonner

In Family Fortunes, father-and-son team Bill and Will Bonner present a radical new way to look at family money along with the practical advice you need to build — and maintain — multi-generational wealth. Filled with invaluable advice for making money and keeping it in the family, the book illustrates why family money is the most dynamic, forward-looking capital in the world, and how your family can cash in on it for generations to come.

36. Influence: The Psychology of Persuasion

By: Robert Cialdini

Considered by many to be the Bible of persuasion, Dr. Cialdini’s Influence was one of the first books to explore the irrationality of human decision making and helped put the field of behavioral economics on the map. Through dozens of fascinating real life studies, you’ll learn the six universal principles, how to use them to become a skilled persuader—and how to defend yourself against them.

37. Antifragile: Things That Gain from Disorder

By: Nassim Nicholas Taleb

Fragile systems break under stress, robust systems resist it, and antifragile systems benefit from it. That’s the premise of Taleb’s groundbreaking work, Antifragile. That we should not only prepare for risk, uncertainty and chaos, but invite it, is a revolutionary idea, but Taleb makes a strong case. Throughout the book, he explores the state of politics, urban planning, finances, economics and medicine to illustrate the necessity of building antifragile systems if we want to thrive in this world.

38. Poor Charlie’s Almanack: The Wit and Wisdom of Charles T. Munger

By: Peter D. Kaufman & Charlie T. Munger

Pound for pound, one of the most important books I’ve ever read, and one that has had a profound impact on my thinking. It should be no surprise to readers of FS that Charlie Munger and Warren Buffet are the two people who have influenced me the most, and this book is a collection of much of the wisdom that attracted me to their philosophies on life, investing, and how I look at the world. And yes, while the book is a little pricier than most, if it were 20x the price, it would still be an amazing value.

39. The Brain that Changes Itself

By: Norman Doidge

For centuries it was thought that the brain stopped developing after a period of time, and that it was a very rigid process. In this book, Norman Doidge explores what scientists call “neuroplasticity” and how nearly everything we once believed about the brain is wrong. The brain is fluid, constantly remapping and rewiring to make its job more efficient. Dr. Doidge shares powerful stories of people who relearn to speak after a stroke, overcome debilitating vertigo, even a blind man who learns to “see.” As it turns out, you can teach an old dog new tricks.

40. The Great Mental Models, Volume 1: General Thinking Concepts

A thorough understanding of these 9 models will, without a doubt, improve the way you approach problems, consider opportunities, and make difficult decisions.

And there you have it — a list of books on decision making that should give you a great starting point. Let us know if there was a book we missed that needs to be on the list!