Chapter I
Books Associated with This Book
These books had a huge impact on me either in terms of inspiring the work (the three biographies) or in terms of helping us think about shaping and organizing the framework.
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2006
Setting the Table: The Transforming Power of Hospitality in Business
One of the first three books that birthed the idea for Runnin' Down a Dream. Danny's book shares the story of his success but also recounts a lifetime of learning about the hospitality business. Lessons for everyone.
2002
Knight: My Story
I originally read this book as a basketball fan, but I discovered Knight was one of the most ambitious learners you will ever discover (and one who would eventually become an ambitious teacher as well). If you want to attack a new career, do it with the fervor and gumption Knight did.
2004
Chronicles: Volume One
What I love about this story is how intentional Dylan was. He called himself a "musical expeditionary." One person called him a sponge. He studied, studied, studied. His 2022 book, The Philosophy of Modern Song, shows that he has never stopped learning and studying his industry.
2019
Range: Why Generalists Triumph in a Specialized World
This second part of Range does a deep dive on what I would call external learning and the breakthroughs that come from borrowing far analogies. We mention this in both Principle Two: Hone Your Craft and Principle Four: Embrace Your Peers—encouraging you to step a bit further away from center as you evolve.
2022
Build: An Unorthodox Guide to Making Things Worth Making
My good friend wrote an amazing book that is partly an account of his historical journey and partly a playbook for new founders. It appropriately expresses Tony's independent spirit. You never dent the world using the traditional strategy.
2020
Blowing My Way to the Top: How to Break the Rules, Find Your Purpose, and Create the Life and Career You Deserve
Somewhere in our cowriting journey, someone suggested to us that the book that best illustrated our original speech was this one. Jen's rise from next to nothing to the top of her field is awe inspiring. But in her personal account of that trajectory you see so many bold and intentional steps. They all paid off.
1970
What Color Is Your Parachute?
This is a great book for anyone who doesn't have confidence about which direction they want to go. Time-tested and worth your time. It may not give you an exact answer, but you will definitely leave with a better perspective and multiple options to explore.
2016
Designing Your Life: How to Build a Well-Lived, Joyful Life
Burnett and Evans take a modern approach to helping you find your direction, with less introspection than What Color Is Your Parachute? and more prototyping and scenario planning. Many exercises are provided. If you need help with that first step of identifying your core curiosity, I say you must read both books.
2003
Moneyball: The Art of Winning an Unfair Game
This extremely well-known book that went on to become a blockbuster movie had a big effect on Sam Hinkie, inspiring him to leave Bain and Australia to chase his dream job and completely changing his life.
2016
Grit: The Power of Passion and Perseverance
My cowriter Michael and I had the privilege of talking to Professor Duckworth about our book. Her own bestselling book Grit drives home the notion that effort can easily beat talent and reinforces this with studies. When you know the path you want to take, Grit will give you the tools (and support) you need to give it your all.
2006
Mindset: The New Psychology of Success
The definitive book on self-driven external learning. Satya Nadella credits this book with changing the culture at Microsoft—which led to perhaps the biggest turnaround story in the history of business. It's impossible to continue to "hone your craft" throughout your career without a growth mindset.
2022
The Power of Regret: How Looking Backward Moves Us Forward
Our book starts with the finding that over half of the population eventually has career regret and would like a "do-over." Daniel Pink teaches you to put that nagging "regret" voice to work and let it power changes in your life. If you are having trouble with the boldness required to leap toward something new—read this!
2011
Swing Your Sword: Leading the Charge in Football and Life
We mention Mike Leach only briefly in the book, but his spirit was with both of us throughout the entire writing process. We simply love his story and his "way." Mike rose to the top of his dream job by abandoning a legal career and starting over at the very, very bottom. Also, his journey was prototypical of this book: learning widely, connecting everywhere, and leaving a massive mark on the game.
Chapter II
A Few Books on Writing
My cowriter Michael and I are huge fans of modern storytelling in nonfiction writing. We first connected in a conversation where we discussed the key nuances of this writing art form.
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2005
The New New Journalism: Conversations with America's Best Nonfiction Writers on Their Craft
This book on using storytelling techniques in modern nonfiction writing is a follow-up to a previous book on the same topic called The New Journalism, by Tom Wolfe. The book studies the key elements used by the modern greats of nonfiction writing: Malcolm Gladwell, Michael Lewis, Jon Krakauer, and others. I have read everything those three have written—and their writing has had a major influence on me and this book.
2012
The Storytelling Animal: How Stories Make Us Human
Gottschall argues that humans are inherently "storytelling animals." He explains the science behind why this is the case and the implications for everyday life.
2000
On Writing: A Memoir of the Craft
King's own career could have easily been one of the core stories written in our book. It has all the pieces that we describe. What's great is that he took the time to write a book about the way he writes, and why, and what's important to him. This is a literary classic, a must-read for aspiring writers, and another story that might inspire you to chase a nonobvious career.
Chapter III
Great Self-Help Books
In many cases the people we were studying would go through a time where they read one, two, or maybe more classic self-help books. And in each case, something in one of those books gave them a push in the right direction.
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1936
How to Win Friends and Influence People
Warren Buffett often says, "The most important degree I have is from Dale Carnegie. Without it, I wouldn't be where I am." This is a foundational book about interpersonal skills that is as important today as it was in 1936 when he wrote it.
1967
Move Ahead with Possibility Thinking
An active minister, Schuller believed in the transformational power of what he called "possibility thinking"—the exploration of what could go right. If you aim to shoot for the stars with a new dream job, this attitude shift will likely help.
1989
The Seven Habits of Highly Effective People
Arguably the grandaddy of the category, with over twenty-five million copies sold, Seven Habits gives you the tools you need to be successful and to do it in the right way. An important foundational read for anyone.
1991
Awaken the Giant Within
Robbins is one of the most successful motivational speakers in the world. He is exceptional at giving you the boost you need to kick it into gear and start doing what you inherently want to do. If you know what job you want to go chase but feel you don't have the gumption or energy to go do it, Robbins's book might be the key.
2018
Atomic Habits: An Easy and Proven Way to Build Good Habits and Break Bad Ones
If you want to chase your dream job, you will need to be productive and efficient. Atomic Habits teaches you how small changes in how you go about your life can make that happen.
2006
Stumbling on Happiness
Some might categorize this book under behavioral psychology, but I've included it here intentionally. If you're going to commit to a long pursuit of your dream job, it's important to ensure that the destination will truly make you happy. Gilbert's book serves as an insightful checkpoint, prompting you to confirm that your goals and values align clearly with the effort you're about to undertake.
1986
Finite and Infinite Games
It is super important to understand whether you are playing a finite game or an infinite one. Most of our perspective about competition and game strategy comes from finite games. Many of the issues you face in life, including your career, are different. And your strategy should reflect that. Always know which is which.
2023
The Creative Act: A Way of Being
As mentioned earlier in the book, if you intend to chase a dream job in any creative field, this book is a must-read. Rick has a proven ability to maximize the creative output of a diverse set of talented individuals. These are his life lessons that could help you as well.
Chapter IV
Favorite Books for Founders
I have often been asked what books I recommend for founders. I have settled on these six below and would probably add a seventh with Fadell's Build, except that we have already listed it above in the first section.
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1962
The Structure of Scientific Revolutions
Kuhn introduced the concept of "paradigm shifts," describing how science progresses not linearly but through revolutionary shifts in thinking. Such shifts create massive start-up opportunities. A critical book to understand innovation, disruption, and the evolution of ideas.
1980
Competitive Strategy: Techniques for Analyzing Industries and Competitors
Most founders have never taken a business class. You need some structures and frameworks for how to analyze and critique different business decisions and strategies. This is an excellent place to start. A cornerstone read.
1991
Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers
Moore figured out that there is a classic go-to-market strategy for most start-ups that sell to enterprises (businesses). The key is to attack the first customers first (innovators and first adopters). The trick is to know how to do that correctly and then eventually to cross the chasm. Many start-ups die that don't follow this advice.
1997
The Innovator's Dilemma: When New Technologies Cause Great Firms to Fail
Like Crossing the Chasm, Christensen's book identified a "truism" that holds for most technology business. The reason that a "start-up" can break in and take share from an "incumbent" is that the incumbent's product gets bloated. This "rotation" around new tech trends is pervasive, but to be successful you have to play it right.
2016
Shoe Dog: A Memoir by the Creator of Nike
The story of Phil Knight and the birth of Nike. So well written. So many great stories. A window into just how many times the company almost didn't make it. In the end a gritty story of business success that should inspire you.
1995
Startup: A Silicon Valley Adventure
We all study successes, and there are plenty in this book—but sometimes it's even more valuable to learn from failure. Go Corp had everything: the best founder, a talented team, and top VCs—but it still didn't succeed. Kaplan tells the story in captivating detail, providing a humbling reminder of how difficult entrepreneurship can be. The silver lining? Most of the individuals involved went on to achieve great things afterward.
Chapter V
Books on Wall Street and Investing
I am very happy that my career veered through Wall Street before heading out to Silicon Valley. The experience was thrilling, and I learned a ton along the way. It's a special place with plenty of very smart people.
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1949
The Intelligent Investor
Warren Buffett cites this as the most important book on investing written by the man you now know was his key mentor. What else is there to say?
1973
A Random Walk Down Wall Street
This is the first book everyone should read before they think about investing. It provides a clear overview of how capital markets function, along with the essential math you need to assess the probability of success between aggressive and more conservative (perhaps even boring) investment approaches.
1989
One Up on Wall Street
This is the book that got me hooked on investing. Super practical and approachable, it gives readers the confidence needed to enter the stock market. However, I still recommend reading A Random Walk Down Wall Street first!
1989
Liar's Poker: Rising Through the Wreckage on Wall Street
Lewis's debut book offers a compelling insider's view of Wall Street. Though Lewis intended it as a cautionary tale, many readers, myself included, were instead drawn to its depiction of the excitement and fast-paced nature of finance.
2006
More Than You Know: Finding Financial Wisdom in Unconventional Places
My good friend illustrates how psychology, philosophy, and science intersect with investing. He skillfully addresses the roles of skill, luck, and behavioral biases in financial decision-making.
2010
The Big Short: Inside the Doomsday Machine
Another home run by Lewis, this book deeply explores the causes of the 2008–09 financial crisis and the mortgage collapse. It provides an insightful view into how and why Wall Street can be deeply flawed.
2014
Flash Boys: A Wall Street Revolt
Lewis again exposes imperfections in the American trading markets, this time delving into high-frequency trading and revealing how certain market players created unfair advantages.
2018
Billion Dollar Whale: The Man Who Fooled Wall Street, Hollywood, and the World
Simply too captivating to miss. This gripping account chronicles Jho Low's massive fraud involving the Malaysian sovereign wealth fund and the numerous accomplices and high-profile connections he made along the way. It reads even better than fiction.
Chapter VI
Fantastic Business Books
Here are a few gems from my collection of favorite general business reads. No matter what industry you're in, these books offer powerful insights and practical wisdom to elevate your game.
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1988
Swim with the Sharks Without Being Eaten Alive
Providing classic negotiation and networking wisdom, this book is a straightforward, highly practical, and foundational read. It can serve as your introduction to sales, negotiation, and management—all things you will need—and can easily be the first business book you read.
1990
Customers for Life
I read this in business school. A local Texas car dealership magnate offers lessons for anyone who runs a service business. Really good.
1991
Getting Past No: Negotiating in Difficult Situations
An essential guide to overcoming difficult negotiations by focusing on empathy, patience, and strategic thinking. Ideal for those frequently navigating complex deals or disputes.
2001
Good to Great: Why Some Companies Make the Leap...and Others Don't
A must-read for anyone aiming to understand what separates truly outstanding companies from the merely good. Timeless lessons on leadership, culture, and disciplined management. One of the classics. Valuable to have in your vault.
2012
The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing
Super insightful for understanding the contribution of luck versus skill in success. Essential for decision-makers and investors aiming to sharpen analytical thinking. Great read, as the author covers many different industries.
2016
Negotiating the Impossible: How to Break Deadlocks and Resolve Ugly Conflicts
This is an advanced-level negotiation course offering modern, sophisticated strategies for your toughest situations. Highly recommended for experienced negotiators or executives facing high-stakes scenarios. Deepak is one of the smartest people I know.
2021
Play Nice but Win: A CEO's Journey from Founder to Leader
As discussed previously, I met Michael in 1994. His success even then was unbelievable, but since then he has continued to grow, pivot, and extend the company. The structure of this book inspired what we did with our own book. Michael alternated chapters between the history of Dell and chapters on his fight with activists for the company. Make sure you listen to the audiobook to pick up on Michael's emotions.
Chapter VII
Behavioral Science Books
I have always been drawn to behavioral science and behavioral psychology books because they help us understand how our minds actually work, rather than how we think they should work.
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1984
Influence: How and Why People Agree to Things
The author brilliantly breaks down the psychology behind persuasion, revealing how seemingly insignificant details can significantly influence decisions and behavior. Essential for anyone interested in human behavior and marketing.
2000
The Tipping Point: How Little Things Can Make a Big Difference
The first of many big hits for Malcolm Gladwell. Explores how small ideas or trends reach critical mass to become major phenomena. Essential for understanding virality, marketing strategies, and consumer behavior.
2005
Blink: The Power of Thinking Without Thinking
Investigates the power and pitfalls of intuition and rapid decision-making, revealing how our unconscious mind can lead us toward effective—or flawed—judgments.
2008
Predictably Irrational: The Hidden Forces That Shape Our Decisions
Ariely reveals the surprising ways humans consistently act irrationally, challenging assumptions about rational decision-making. Highly readable, insightful, and often entertaining.
2008
Nudge: Improving Decisions About Health, Wealth, and Happiness
This powerful exploration of how subtle shifts in framing and choice architecture can lead to significantly better decisions offers actionable insights for policymakers, businesses, and individuals.
2009
Think Twice: Harnessing the Power of Counterintuition
Another insightful read from Mauboussin, this book challenges readers to question intuitive decision-making, highlighting common pitfalls and providing strategies to improve outcomes.
2011
Thinking, Fast and Slow
Kahneman's groundbreaking book explores the dual systems of thought—fast, intuitive judgments versus slow, analytical reasoning—and explains why we make systematic errors in judgment and decision-making. This is now the bible. Long but worth it.
2018
Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts
Annie Duke, a former poker champion, demonstrates how embracing uncertainty and probabilistic thinking can dramatically improve decision-making in business, investing, and daily life. Her "Always think about it like a bet" is quite provocative.
Chapter VIII
How the World Works
These are some of my favorite books that explore the big picture of how the world operates. They're profound, substantial, and arguably the most important of all the books listed here—but also are among the most challenging to digest.
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1986
The Blind Watchmaker: Why the Evidence of Evolution Reveals a Universe Without Design
Dawkins describes evolution by natural selection with clarity and precision, arguing persuasively that complexity and order emerge naturally without design. I concur. This is crucial reading for appreciating evolutionary thinking applied broadly across disciplines.
1992
Complexity: The Emerging Science at the Edge of Order and Chaos
This is my favorite book. It's about the rise of the Santa Fe Institute, where I now sit on the board. No other book has affected me quite the way this one has. The institute and the book study the dynamics of complex multivariable systems. Most important systems are complex and very hard to study and understand. Yet many assume they are simple.
2008
Thinking in Systems: A Primer
Meadows helps managers understand that their products and services exist within complex systems. Without this understanding, unintended consequences are prevalent. Conversely, fully grasping system dynamics can help identify precise points for effective change.
2010 / 2020
The Rational Optimist & How Innovation Works
I recommend you read them in order, one right after the other. Ridley gives us an ultrawide time lens to show how technology spreads and drives prosperity gains. His concept of "ideas having sex" is etched in my brain. I wish every policymaker could be forced to read both of these.
2011
Sapiens: A Brief History of Humankind
Harari's groundbreaking narrative explores human history, examining how Homo sapiens became the dominant species through unique cognitive and social abilities. It also touches on the critical power of storytelling used by many to control large swaths of the population.
2018
Enlightenment Now: The Case for Reason, Science, Humanism, and Progress
Pinker presents compelling evidence that the Enlightenment ideals of reason, science, and humanism have significantly improved global living conditions. And I am here for it. A critical antidote to pessimism, advocating for continued commitment to rational progress.