Life can sometimes feel like an endless string of problems and setbacks. But what if it didn’t have to be this way? What if, instead of exhausting you and dampening your spirits, every challenge you faced made you tougher and more energized? In The Obstacle Is the Way, Ryan Holiday argues that you have the power to create this kind of life for yourself by changing the way you view your problems.
Holiday explains that choosing to view obstacles in an empowering way is a major tenet of an ancient philosophy called Stoicism, founded in Greece in the third century B.C. According to Holiday, people throughout history have chosen to follow the Stoic tradition and utilized the same empowering strategy to solve their problems: They find the hidden opportunity in any misfortune and use it as a tool to accomplish their chosen goal. This philosophy has enabled people from every walk of life to overcome enormous obstacles and transform themselves into stronger, nobler people in the process.
This guide will teach you the tenets of Stoic problem-solving and how to apply them to the problems in your life. We’ll begin by explaining the basics of how Stoics view the world and the purpose of life—ideas that Holiday calls “The Discipline of Perception.” Then, we’ll explore specific strategies rooted in Stoicism that you can use to solve your problems: First, strategies to master your emotional state that Holiday refers to as “The Discipline of Will,” and second, strategies to efficiently accomplish your goals in the real world that Holiday refers to as “The Discipline of Action.”
Is This Really Stoicism?
It’s a point of contention whether or not The Obstacle Is the Way and other pop-Stoic texts truly fit into the Stoic canon. The Obstacle Is the Way doesn’t claim to be a replacement for the original Stoic texts or even to comprehensively summarize them—Holiday prefers to label it as a book “inspired by” Stoicism rather than one that’s “about” Stoicism. This qualifying statement begs the question: How faithful are the ideas in this book to the original Stoic teachings?
There’s no single founding document of Stoicism outlining exactly what the philosophy represents, but many ideas common across Stoic writings are present in The Obstacle Is the Way. Holiday agrees with the Stoics that through self-discipline, a “sage” can transform their life by becoming undisturbed by external events and learning to control irrational passions.
Holiday’s faithfulness to Stoic writing doesn’t stop there. The three disciplines that form the backbone of Holiday’s book—perception, action, and will—originated in the Roman Stoic text Discourses by Epictetus. These specific English names were coined by Gregory Hays in the introduction to his translation of Meditations by the Stoic emperor Marcus Aurelius.
However, The Obstacle Is the Way doesn’t perfectly represent the Stoic way of life. Holiday focuses his book on the ways you can use Stoicism to get what you want out of life by amending your approach to problems. Some argue this attitude undercuts the power of “true” Stoicism, which denies the need for material gain and puts greater emphasis on virtuous living. Holiday would likely make the case that while his book doesn’t paint a complete picture of the Stoic worldview, it doesn’t necessarily contradict it, either. As Holiday himself put it, “Stoicism is a philosophy designed for the masses, and if it has to be simplified a bit to reach the masses, so be it.”
We’ve distilled the Stoic problem-solving worldview into two basic truths. These truths are Holiday’s foundational beliefs about the world that lead him to conclude that you can (and should) transform any problem into an opportunity that benefits you.
In our everyday lives, we assign meaning to everything that happens to us, judging events to be either good or bad. Holiday explains that in contrast, Stoics view events neutrally—that is, they observe only the facts of any given situation, without judgment.
In Holiday’s eyes, the positive or negative judgments we make about the events in our lives are nothing more than illusions—they’re often detached from reality. Additionally, Holiday argues that these subjective judgments themselves are what cause much of our suffering. Instead of seeing things as they are, we perceive problems that aren’t really there.
For example, imagine you hear a rumor that the company you work for is operating at a loss and several employees need to be fired. You fear you’re going to lose your job and begin to panic. Holiday would argue that the risk of getting fired isn’t the problem—your warped, negative view of the situation, causing fear and panic, is the problem. These feelings don’t necessarily reflect reality—even if you are fired, there’s a chance you might immediately find a better job, and getting fired will have been one of the best things to ever happen to you.
Cognitive Behavioral Therapy Is About Cultivating Objectivity
Holiday’s claim that subjective perceptions cause most of our suffering has significant support from the field of psychology. In the popular branch of psychotherapy known as cognitive behavioral therapy, or “CBT,” a patient and therapist work together to identify the patient’s harmful and inaccurate perceptions of reality; replace them with healthier, more realistic beliefs; and build habits of responding to negative emotions in constructive ways.
In Feeling Great, psychiatrist David Burns explains that people who suffer from anxiety and depression experience the types of distorted, irrational negative thoughts that Holiday mentions. For example, they overgeneralize, telling themselves that because they did one thing wrong, they are “bad people” doomed to make things worse for the rest of their lives. Or, they “discount the positive,” devaluing their successes and claiming that they don’t really count. Burns agrees with Holiday that seeing things objectively is a trainable skill, and for this reason, he offers readers many exercises to help them perceive events without judgment.
As Holiday explains, the cornerstone of the Stoics’ problem-solving philosophy is that you can find a silver lining in any circumstance in your life, no matter how dire it seems. Even if the only benefit you can find in an obstacle is an opportunity to practice acting virtuously, for instance, by restraining your anger or forgiving a misdeed, you’ve gained something of value.
Once you identify the upsides of a situation, Holiday claims that you can choose to be grateful that it happened. In short, no event is inherently good or bad—your perspective determines whether it’s good or bad. By choosing to claim the gift available in any problem, you remove its ability to hurt you.
For example, if you’re heartbroken by the death of a grandparent, you can use the tragedy as a reminder to treasure the time you still have with your parents. Shared grief may bring you closer to your emotionally distant siblings. You could even use this event as a reminder of your own death and start living life to the fullest.
Additionally, Holiday argues that seeing your problems as opportunities helps you overcome them, as you’ll be more likely to persevere through setbacks and discover hidden solutions. In other words, your perception of a situation determines how you will respond to it. In this way, what you tell yourself about an obstacle significantly influences how easy or difficult it is to overcome.
The Right Perspective Makes People “Lucky”
Holiday argues that you can bring a positive attitude to any situation, but how exactly does it help you overcome your problems? Over several years, psychologist Richard Wiseman conducted a study to determine what separates lucky people from unlucky people. After examining and experimenting with hundreds of people who described themselves as either “exceptionally” lucky or unlucky, he found that the difference was entirely behavioral and had much to do with the subjects’ perspective on life events.
Wiseman asked subjects to imagine that they were at a bank during a robbery and wound up getting shot in the arm. Unlucky people labeled this as an unlucky situation, mourning that they happened to be in the bank when this crime occurred, while lucky people classified this as a lucky situation, noting that they could have easily been shot in the head and feeling grateful that they survived. By comparing situations to worse alternatives, they were able to recontextualize any situation into something positive, proving Holiday’s assertion that it’s possible to appreciate the upsides of any situation.
The lucky subjects who approached life with this positive attitude thrived because they took more risks, sought out more unfamiliar situations, and were more receptive to positive opportunities than their unlucky counterparts. These characteristics made them more likely to stumble into romantic success and promotions at work. As Holiday would predict, their optimistic perceptions determined how they responded to life events, making their lives demonstrably “luckier.”
So far, we’ve outlined two truths from Stoicism that Holiday asserts will help you fulfill your wildest ambitions. For the rest of this guide, we’ll be discussing specific strategies to help you live according to these truths: ways to reorient your thinking and overcome any problem. First, let’s look at Holiday’s internal, emotional strategies for success.
Holiday emphasizes the importance of emotional regulation—intentionally deciding which emotions you will allow to influence your behavior. It’s a simple fact of life: You will frequently feel emotions (such as fear and anger) that work against you and push you away from your goals. If you don’t exert control over these unhelpful emotions, you won’t be able to take advantage of the opportunities within your obstacles.
(Shortform note: Holiday’s stance on emotion regulation is less extreme than the original Stoic teachings. Holiday sees negative feelings as more or less an inevitable part of life, defining emotional discipline as the ability to act despite your unhelpful emotions. On the other hand, traditional Stoics believed that by exerting your rationality, you can learn to completely cleanse yourself of harmful emotions.)
Holiday claims that by slowing down and analyzing your situation logically, you can soothe unhelpful, impulsive emotions like panic or anger. Whenever you feel yourself being tugged around by your emotions, stop and interview yourself to discover why you feel the way you do. Ask yourself questions, then answer them logically. You can overcome negative emotions by clarifying what irrational beliefs are making you feel this way and replacing them with a logical counterargument.
(Shortform note: In Emotional Intelligence, Daniel Goleman offers a caveat to this advice, noting that thinking over an emotion for too long may extend and intensify your negative feelings. Mental exercises such as Holiday’s self-interview may make you sadder by forcing you to dwell on whatever is making you sad. Instead, Goleman recommends intentionally planning pleasant distractions such as comforting TV or exercise to combat sadness.)
When you’re unable to fully rid yourself of negative emotions, Holiday recommends you transform them into a form that serves you. In particular, when unfair circumstances or pointless constraints frustrate you, Holiday suggests you use that anger as fuel instead of allowing it to make you reckless. Use your calm, rational mind to decide where to commit your energy, then allow yourself to act wildly and impulsively within that context.
(Shortform note: The process Holiday describes here—using your unhelpful emotions to motivate constructive action—is known in psychology as sublimation. Sigmund Freud introduced this concept into the public vocabulary. Although the majority of Freud’s hypotheses have been discredited, the concepts of sublimation and similar psychological defense mechanisms have endured.)
Holiday argues that to achieve your goals, you need resilience woven into your DNA as a permanent feature of your character. He asserts that it’s possible to build this kind of emotional strength with practice over time. Decide where you need to go and resolve that you will do anything it takes to get there, no matter what obstacles get in your way—then do it again. To a certain degree, it’s worth your while to intentionally seek out adversity to train yourself for the greater troubles that lie ahead.
(Shortform note: Holiday’s advice on how to cultivate perseverance can be boiled down to “Toughen up and do it.” On the other hand, in Grit, Angela Duckworth advocates for a gentler path to resilience, one that doesn’t require as much sheer willpower. Duckworth asserts that you can develop grit in stages, initially pursuing something fun that interests and gratifies you, then practicing to achieve superiority, and finally merging your skill with an altruistic purpose. In other words, resilience develops naturally as you pursue satisfying goals.)
Holiday argues that the best way to tackle any fearsome problem or obstacle is to break it down and just focus on finishing one step at a time. Do the first step well, then move on to the next step and the next. Don’t think about the end goal, just what you have to do now. When you have a plan to follow, problems feel less daunting—each step is a psychologically manageable task that you can work up the courage to complete.
(Shortform note: In Eat That Frog!, Brian Tracy notes that when a task reaches a certain size, it becomes impossible to plan out the entire process ahead of time in the way Holiday describes. When your plan involves unknown variables or complex moving parts, the only thing you can do is take the first step and have faith that the next step will reveal itself to you. If you can become comfortable with this uncertainty, taking the task one step at a time will still help you feel less intimidated.)
Holiday asserts that by turning your attention outward and helping others, you can tap into an unlimited source of motivation and strength that will help you overcome obstacles. Negative emotions like anxiety and self-pity fade away when you discover a way to move forward and do good. Whenever you feel stuck, find a way to help someone other than yourself.
(Shortform note: While Holiday frames the feeling of contribution to others as a source of motivation to achieve your virtuous goals, in The Courage to Be Disliked, Ichiro Kishimi and Fumitake Koga make the more extreme argument that these feelings of contribution are the essence of all happiness. Kishimi and Koga assert that happiness is based on self-worth—whether or not you think you’re a “good person”—and contribution to others is the source of all self-worth.)
Holiday’s final strategy to master your emotions is to accept things for what they are. Some aspects of life are impossible to change—for instance, the actions of others, or a tragedy that has already happened. Holding an emotional grudge against a reality you can’t change will only make it more difficult to achieve your goals. Instead, peaceably accept things for what they are.
(Shortform note: In The Happiness Trap, Russ Harris explains how readers can use something called “Acceptance and Commitment Therapy,” or “ACT,” to find happiness in their lives. Harris uses the same rationale as Holiday to support his advice: We should focus on what we can control and peaceably accept whatever is out of our control. Harris, however, gets more specific than Holiday, applying this logic to negative thoughts. If a negative thought pushes you toward something you can change, it’s helpful, so act on it. If it pushes you toward something you can’t change, accept it and ignore it.)
We’ll conclude with a set of Holiday’s strategies to overcome obstacles in the external world, difficult yet rewarding paths to success that require you to transform obstacles into gifts at every turn.
The core of Holiday’s overall strategy for success is to start immediately and rush toward your goal as quickly and aggressively as possible. Consistently putting in effort is how you build the momentum necessary to reach your goals, and momentum is more important than anything else. If you ever stop aggressively moving forward with as much effort as you can muster, instead of overthinking your every step, you risk becoming soft and complacent.
(Shortform note: Holiday warns of the dangers of overthinking, but in The One Thing, Gary Keller argues that if you act without first considering how to optimize your effort, underthinking can be just as harmful. Keller makes the case that even if you’re aggressively taking action toward your goal, you’re wasting your time if you’re not focusing on your “One Thing”—the task that will get you to your most ambitious goal faster than anything else. To find your One Thing, Keller suggests asking yourself “What one thing can I focus on that will have the greatest impact on my overall goal?”)
Holiday acknowledges that if you follow his advice to act aggressively and persistently, you’ll inevitably fail often. However, he sees this as an unequivocally good thing. Trial and error is the most effective way to learn anything. Every failure teaches you how not to do something and forces you to come up with ideas you wouldn’t have normally thought of.
(Shortform note: In Thinking in Bets, professional poker player Annie Duke argues that the best way to learn from your mistakes is to view every decision you make as a bet—a gamble based on the idea that something might be true. This way, you recognize that every belief you have has a chance of being incorrect, and every suboptimal decision you make comes at a cost.)
Holiday asserts that people who habitually fear failure—that is to say, almost everyone—generally assume that they can accomplish far less than they actually can. To avoid this mistake, he advises you to confidently set unreasonably ambitious goals and attempt to do the impossible. He advises you to seek out high-pressure situations like this because they’re most likely to inspire your best work. By focusing on the energizing effect of a big risk, you can transform it from something terrifying into something exciting.
(Shortform note: In The 10X Rule, Grant Cardone argues that most people fail because they don’t set difficult enough goals. How can this be? Most people set average, realistic goals and underestimate the effort it takes to achieve them. When it becomes obvious how much work these goals actually require, they aren’t excited enough to push through the unexpected struggle, so they quit. On the other hand, accomplishing something that seems impossible is a dream that will make you want to put in ten times the effort you normally would.)
Holiday argues that it’s important to remember that eventually, things will go wrong. People will let you down and random disasters will strike—this is the only constant in our unpredictable world. Your only defense is to anticipate what could go wrong and prevent or prepare for it. Holiday recommends making this a core step of your routine: Before taking any action, try to think up contingency plans for everything you can imagine going wrong.
(Shortform note: In The Dichotomy of Leadership, Jocko Willink and Leif Babin argue that while planning for what could go wrong (as Holiday suggests) helps avert painful disasters, overplanning—attempting to prepare a detailed response for every possible setback—can be just as harmful. Trying to predict everything that could go wrong will severely slow you down, and may even halt your progress entirely. At a certain point, this wasted time becomes more costly than it’s worth.)
In many cases, the most successful strategy is that which is least expected. Holiday explains that the conventional strategy—the one other people in your situation use the most often—frequently has the lowest chance of success, as it’s the strategy your enemies and obstacles are the most prepared for. Using an obscure strategy to reach your goal often allows you to succeed with far less effort.
For example, if you’re trying to get your novel published, instead of sending query letters to agents or publishers and burying your pitch among thousands of others, find an unconventional way to make connections in the industry—for instance, locate a nearby writers’ conference to network at and volunteer to help run it.
(Shortform note: In The 48 Laws of Power, Robert Greene claims that even if your unexpected strategy isn’t successful in itself, acting unpredictably is still valuable. When no one understands why you’re doing something, you create an air of intrigue, attracting attention from onlookers. You may even earn their respect as people ascribe sophisticated motives to your actions that you never had.)
The Obstacle Is the Way is an instruction manual on how to solve life’s toughest problems, based on the teachings of the Stoics of Ancient Greece. Ryan Holiday argues that by adopting the Stoics’ historically proven formula for success, you can redirect the forces that typically work against you and will them to push you toward your goals. Once you embrace the truth that events are only “good” or “bad” if you perceive them that way, you gain the ability to transform your pain into power, your limitations into strengths, and your obstacles into opportunities.
Ryan Holiday began his career after dropping out of college at age 19, when Robert Greene, author of The 48 Laws of Power, agreed to take him on as an “apprentice.” A year later, he got a job in the PR department of American Apparel, eventually becoming the company’s director of marketing. During this time, Holiday also founded his own consulting firm Brass Check, which has served such high-profile clients as Tony Robbins and Tim Ferriss. After releasing The Obstacle Is the Way, Holiday’s career as a nonfiction author took off, and he quit marketing to focus on writing full time.
Holiday first encountered Stoicism at 19. Holiday recounts that at this age, he made it a habit to ask as many successful people as possible for book recommendations. He read Marcus Aurelius’s Meditations after Dr. Drew Pinsky, host of the radio show Loveline, recommended it to him and credits this event as a pivotal moment in his life.
Holiday is also the founder of the Daily Stoic blog and currently hosts its daily podcast, offering bite-sized lessons in Stoicism and interviewing top performers from a variety of disciplines. He currently lives on a ranch in Texas, raising cows, goats, chickens, and other animals when he isn’t writing.
Connect with Ryan Holiday:
Publisher: Penguin Random House
Imprint: Portfolio
The Obstacle Is the Way is Holiday’s third book, published in 2014. The book originated from a guest post on Stoicism that Holiday wrote for Tim Ferriss’s blog in 2009. Impressed with the piece, a publisher approached Holiday with a deal for a book on Stoicism, but he declined the offer, as he didn’t think he was yet experienced enough to tackle such an important project. He shelved the book for several years.
Holiday became moderately infamous after the release of his first book Trust Me, I’m Lying (2012), an exposé of the Internet news media in which he confessed to manipulating online publications into spreading disinformation for free viral publicity. His reputation as a shady marketing expert faded with the release of The Obstacle Is the Way, replaced by a public image centered around Stoicism.
Holiday followed The Obstacle Is the Way with several other books on modern Stoicism, including Ego Is the Enemy (2016) and Stillness Is the Key (2019), which are sold with this book as a boxed trilogy. All three books are written in a similar style: short chapters of historical anecdotes intended to illustrate specific Stoic principles from a self-help perspective. Holiday also published The Daily Stoic with co-author Stephen Hanselman in 2016, a “daily devotional” split into a year’s worth of brief lessons in Stoicism. Holiday’s first book in a new series based on Stoicism’s cardinal virtues, Courage Is Calling, was published in 2021.
Holiday primarily draws his ideas from the Stoics’ original writings. He specifically cites the ancient works Meditations by Marcus Aurelius, Letters from a Stoic by Seneca, and Discourses by Epictetus as his main inspirations.
Holiday is far from the first person to bring these ideas into the modern age. Psychologist Aaron T. Beck, who in the 1960s developed what later would become modern cognitive therapy, credits Stoicism as the philosophical basis behind the therapeutic approach. In addition, academics turned greater attention to Stoicism as the topic of “virtue ethics” became popular throughout the late 20th century. Finally, the rise of the Internet and communities such as the Modern Stoicism Organization helped turn Stoicism into a major contemporary movement, as Stoicism’s self-help applications attracted a broad audience. Books like A Guide to the Good Life (2008) and Stoicism and the Art of Happiness (2018) capitalized on and contributed to this wave of pop-Stoicism.
Holiday argues that most modern books about Stoicism obscure its main ideas and end up reducing their core value. In Holiday’s eyes, the only other modern Stoic thinker worth reading is the French philosopher Pierre Hadot. He cites Hadot’s books Philosophy as a Way of Life (1995) and The Inner Citadel (2001) as successful attempts to clarify Stoic ideas for practical living.
Soon after it was written, The Obstacle Is the Way became a cult classic among famous high performers, most notably professional athletes. Prior to their 2014 Super Bowl win, the coaches of the New England Patriots distributed copies of the book to the entire team. The media continued to report as players and coaches on other NFL teams, including the Seattle Seahawks and the New Orleans Saints, sang the book’s praises. The Obstacle Is the Way infiltrated the MLB (Chicago Cubs), the NBA (Miami Heat), and even the Olympics—athletes and coaches on the US women’s soccer and volleyball teams and US men’s wrestling and gymnastics teams swear by it.
The Obstacle Is the Way became more famous as celebrities from other fields professed their admiration, including Arnold Schwarzenegger, rapper LL Cool J, author Steven Pressfield, and NBC sportscaster Michele Tafoya.
This growing grassroots following eventually led to The Obstacle Is the Way becoming the #1 e-book on the New York Times bestseller list in 2019, five years after it was published. The New York Times credits Ryan Holiday for popularizing Stoicism as a self-help movement with this book.
The Obstacle Is the Way received a positive review from Forbes on release, who described it as “an inspiring read for anyone faced with adversity,” but the book flew under the radar of other major publications.
Fans celebrate the book as life-changing self-help and attest that it helps them act more virtuously. They praise Holiday for condensing some of the Western world’s most valuable wisdom into a form that’s quick and easy to digest. Supporters also enjoy the storytelling style and examples from history that Holiday uses to present his ideas.
Common criticisms of the book include the fact that it’s philosophically shallow, especially compared to other popular contemporary books on Stoicism. The book is mostly made up of variations on the same idea. Additionally, many complain that Holiday doesn’t offer enough actionable advice—he tells you to change your perspective on obstacles without fully explaining how to do so.
The Obstacle Is the Way isn’t intended to be a comprehensive guide to Stoicism—it’s a self-help book intended for a broad audience. Holiday himself admits to simplifying Stoic ideas to make the book more accessible. As such, the book at times tends to appeal more to the reader’s emotions than their sense of logic. Holiday prefers to present ideas to the reader and hope they resonate rather than to convince the reader of his argument.
The Obstacle Is the Way is divided into three parts: “Perception,” “Action,” and “Will,” which Holiday argues are three foundational domains you must master to solve problems like a Stoic.
Holiday’s decisions on which chapters to place in each section can appear arbitrary. Some of the chapters Holiday places in the “Action” section occur internally (“Practice Persistence,” “Channel Your Energy”), while some of the “Perception” and “Will” chapters involve tasks that could be placed on a to-do list (“Think Differently,” “Anticipation (Thinking Negatively)”). Additionally, the line between “Perception” and “Will” gets a little blurred, as they both involve perceiving negative situations in an empowering way.
In this guide, we’ve reorganized Holiday’s ideas into new categories: Philosophy, the Internal Fight, and the External Fight.
First, we’ve placed most of the ideas in Holiday’s “Perception” section in a “Philosophy” section at the beginning of the guide, as they serve as the basis of Holiday’s problem-solving approach. We’ve grouped some of Holiday’s foundational assumptions from the other parts of the book into this section to complete the picture of his worldview.
Second, we’ve reorganized the other ideas from the book into two categories: Instead of “Will,” we have “The Internal Fight,” strategies that deal with your internal world of thoughts and emotions. Instead of “Action,” we have “The External Fight,” strategies that deal with taking action in the external world. This delineation clears up the ambiguity in Holiday’s organization.
Additionally, unlike Holiday, we’ve placed the internal strategies before the external strategies, as you need a disciplined emotional state before you can properly execute strategies in the physical world.
Throughout this guide, we’ll explain how Holiday’s self-help style of Stoicism compares to the broader Stoic philosophy that inspired it. We’ll also supplement Holiday’s advice on accomplishing your goals with related texts from the self-help world, including Grit by Angela Duckworth and Thinking in Bets by Annie Duke.
Life can sometimes feel like an endless string of problems and setbacks. But what if it didn’t have to be this way? What if, instead of exhausting you and dampening your spirits, every challenge you faced made you tougher and more energized? In The Obstacle Is the Way, Ryan Holiday argues that you have the power to create this kind of life for yourself by changing the way you view your problems.
Holiday explains that choosing to view obstacles in an empowering way is a major tenet of an ancient philosophy called Stoicism, founded in Greece in the third century B.C. The Obstacle Is the Way is a Stoic’s guide to solving problems, outlining the principles that heroes throughout history used to exert their will over a hostile world.
According to Holiday, people throughout history have chosen to follow the Stoic tradition and utilized the same empowering strategy to solve their problems: They find the hidden opportunity in any misfortune and use it as a tool to accomplish their chosen goal. This philosophy has enabled people from every walk of life to overcome enormous obstacles and transform themselves into stronger, nobler people in the process.
This guide will teach you the tenets of Stoic problem-solving and how to apply them to the problems in your life. Part 1 will be “Philosophy,” explaining the basics of how Stoics view the world and the purpose of life—ideas that Holiday calls “The Discipline of Perception.”
In Parts 2 and 3, we’ll explore specific strategies rooted in Stoicism that you can use to solve your problems. Part 2 will be “The Internal Fight,” strategies to master your emotional state that Holiday refers to as “The Discipline of Will.” Part 3 will be “The External Fight,” strategies to efficiently accomplish your goals in the real world that Holiday refers to as “The Discipline of Action.”
Is This Really Stoicism?
It’s a point of contention whether or not The Obstacle Is the Way and other pop-Stoic texts truly fit into the Stoic canon. The Obstacle Is the Way doesn’t claim to be a replacement for the original Stoic texts or even to comprehensively summarize them—Holiday prefers to label it as a book “inspired by” Stoicism rather than one that’s “about” Stoicism. This qualifying statement begs the question: How faithful are the ideas in this book to the original Stoic teachings?
There’s no single founding document of Stoicism, making it difficult to pin down precisely what the philosophy represents. The Obstacle Is the Way is most directly based on Meditations, a philosophical treatise by the Roman emperor Marcus Aurelius. Meditations, along with other Roman Stoic texts, focused far more on the ethics of Stoic philosophy and their applications to daily living than the original Greek Stoic writings, which focused more on observation and classification of the universe. Holiday writes in the tradition of the Roman Stoics, adamant that Stoic philosophy is meant to be applied.
Many ideas common across Stoic writings are present in The Obstacle Is the Way. Stoics across the board agreed that virtue is both the purpose of life and the greatest source of fulfillment. Through self-discipline, a “sage” can transform their life by becoming undisturbed by external events and learning to control irrational passions—two ideas that contribute to our modern concept of the word “stoic.”
Holiday’s faithfulness to Stoic writing doesn’t stop there. The three disciplines that form the backbone of Holiday’s book—perception, action, and will—originated in Discourses by Epictetus, another Roman Stoic text that directly influenced Marcus Aurelius. These specific English names were coined by Gregory Hays in the introduction to his translation of Meditations.
Holiday doesn’t cover every main idea of Stoicism, however. He’s left out most of the philosophy’s metaphysical, pseudo-religious beliefs, likely because he wants to appeal to a broad secular audience. For example, one central tenet of Stoicism is a belief in logos, a rational godlike force at work creating an ordered universe—and a force that Holiday doesn’t mention. Additionally, Holiday emphasizes how you can use Stoicism to get what you want out of life by amending your approach to problems; however, some argue that this approach undercuts the power of “true” Stoicism, which denies the need for material gain and puts greater emphasis on virtuous living.
Holiday would likely make the case that while The Obstacle Is the Way doesn’t paint a complete picture of the Stoic worldview, it doesn’t necessarily contradict it, either. As Holiday himself put it, “Stoicism is a philosophy designed for the masses, and if it has to be simplified a bit to reach the masses, so be it.”
We’ve divided Part 1, our discussion of the Stoic worldview, into three basic truths. These truths are Holiday’s foundational beliefs about the world that lead him to conclude that you can (and should) transform any problem into an opportunity that benefits you.
In our everyday lives, we assign meaning to everything that happens to us, judging events to be either good or bad. Holiday explains that in contrast, Stoics view events neutrally—that is, they observe only the facts of any given situation, without judgment.
In Holiday’s eyes, the positive or negative judgments we make about the events in our lives are nothing more than illusions—they’re often detached from reality. We invent narratives of cause and effect that aren’t true, convincing ourselves that external occurrences have far greater power over us than they really do.
Holiday argues that in reality, these subjective judgments themselves are what cause much of our suffering. Instead of seeing things as they are, we perceive problems that aren’t really there, which is the real problem. When things don’t turn out the way we think they should, we assume that we’re doomed to suffer, which frightens and disempowers us. However, this forecasted suffering never has to come to pass. As the Stoic philosopher Seneca put it, we suffer more often in imagination than in reality. By simply learning to see these events objectively, as neither good nor bad, we spare ourselves a great deal of pain.
For example, imagine you hear a rumor that the company you work for is operating at a loss and several employees need to be fired. You fear you’re going to lose your job and begin to panic. Holiday would argue that the risk of getting fired isn’t the problem—your warped, negative view of the situation, causing fear and panic, is the problem. This rumor isn’t necessarily an unfortunate turn of events: You don’t know that it’s true, or that you would be one of the employees fired.
Even if you are fired, there’s a chance you might immediately find a better job, and getting fired will have been one of the best things to ever happen to you. By fearing the worst, you’re suffering unnecessary emotional stress that makes it more difficult to work toward a solution.
Seeing events objectively, as Stoics see them, doesn’t come naturally—Holiday frames it as a skill you need to intentionally hone. Whenever you catch yourself lamenting over your own misfortune, stop and remind yourself that there’s no such thing as misfortune. Later, we’ll explore some specific strategies to help you do this.
Cognitive Behavioral Therapy Is About Cultivating Objectivity
Holiday’s claim that subjective perceptions cause most of our suffering has significant support from the field of psychology. In the popular branch of psychotherapy known as cognitive behavioral therapy, or “CBT,” a patient and therapist work together to identify the patient’s harmful and inaccurate perceptions of reality; replace them with healthier, more realistic beliefs; and build habits of responding to negative emotions in constructive ways.
In Feeling Great, psychiatrist David Burns explains that people who suffer from anxiety and depression experience the types of distorted, irrational negative thoughts that Holiday mentions. For example, they overgeneralize, telling themselves that because they did one thing wrong, they are “bad people” doomed to make things worse for the rest of their lives. Or, they “discount the positive,” devaluing their successes and claiming that they don’t really count. Burns agrees with Holiday that seeing things objectively is a trainable skill, and for this reason, he offers readers many exercises to help them perceive events without judgment.
The success of cognitive behavioral therapy in clinical settings supports Holiday’s argument about the power of perspective. A meta-analysis of over a hundred independent studies found that cognitive behavioral therapy is indeed effective, especially in treating anxiety disorders, stress disorders, bulimia, and problems with anger control.
Stoics believe that no situation is objectively good or bad, without exception. This includes the condition that many see as the universal curse of humanity: our own mortality. Holiday argues that the reality that we’re going to die someday—perhaps even today—is a neutral fact, like anything else, that we can choose to interpret however we wish.
Holiday points out that the fact we’re going to die actually offers us a number of benefits, as long as we see the situation objectively enough to notice and claim them. An awareness that our days are numbered actually makes many things easier for us—we’re more readily grateful for the good things we have in life, and we’re motivated to pursue what we truly think is important instead of wasting time living an unfulfilled life. These are gifts we wouldn’t have if not for our own mortality—which, according to Holiday, proves that death itself is not necessarily a bad thing. Like everything else in our lives, it’s a neutral fact of life.
We Didn’t Always Fear Death
In Antifragile, Nassim Nicholas Taleb argues that humans in modern society fear death far more than they did back in classical antiquity. He asserts that before the Enlightenment, the average person’s goal wasn’t to avoid death but to die in a noble way that accomplished something for future generations—for example, to die in battle defending your nation, or to leave behind a business that will help your children live a better life. This supports Holiday’s argument that, given the right perspective, even a situation as grim as your own death can be something worth celebrating.
Taleb advocates for a return to this collective-minded attitude toward death. In his eyes, our focus on our own lives as an end goal causes our society to be more fragile. For example, by accruing governmental debt and depleting natural resources, we’re enriching ourselves at the expense of future generations, damaging the human race as a whole. Instead of trying to live longer, we should be trying to live purposefully, die, and make room for others.
Holiday argues that if you can find a way to use your own mortality as a means to improve your life, you can do the same with any other problem. The cornerstone of the Stoics’ problem-solving philosophy is that you can find a silver lining in any circumstance in your life, no matter how dire it seems. Even if the only benefit you can find in an obstacle is an opportunity to practice acting virtuously, for instance, by restraining your anger or forgiving a misdeed, you’ve gained something of value.
Once you identify the upsides of a situation, Holiday claims that you can choose to be grateful that it happened. In short, no event is inherently good or bad—your perspective determines whether it’s good or bad. By choosing to claim the gift available in any problem, you remove its ability to hurt you.
Holiday makes it clear that this isn’t an empty truism promising that positive thinking will keep anything bad from ever happening to you. Rather, it means that failures and setbacks can be just as good for you as getting what you want—if you decide to see them that way.
Here are a few examples of how problems could become opportunities:
In situations like these, you don’t need to deny the fact that you would rather things had turned out differently. However, Holiday argues that if you refuse to look for their hidden benefits, you’re actively throwing away a gift that’s been given to you. Every negative event contains gifts like these for you to find.
Another reason it’s so empowering to choose to see your problems as gifts is that your perception of a situation determines how you will respond to it. Holiday argues that if you see your problems as opportunities, you’ll be more likely to persevere through setbacks and discover hidden solutions. In this way, what you tell yourself about an obstacle significantly influences how easy or difficult it is to overcome.
Often, we blame someone or something else for our unpleasant situation, convincing ourselves that there’s nothing we can do to get unstuck. Holiday asserts that on the contrary, the only thing that can ever keep us stuck is our subjective perception of the situation. If you decide there’s nothing you can do, the obstacle you confront will indeed be insurmountable. On the other hand, if you believe that there’s a way forward in any situation, you’ll find it wherever it exists.
The Right Perspective Makes People “Lucky”
Holiday argues that you can bring a positive attitude to any situation, but how exactly does it help you overcome your problems? Over several years, psychologist Richard Wiseman conducted a study to determine what separates lucky people from unlucky people. After examining and experimenting with hundreds of people who described themselves as either “exceptionally” lucky or unlucky, he found that the difference was entirely behavioral and had much to do with the subjects’ perspective on life events.
One of the chief differences between lucky and unlucky people was the way they practiced “counterfactual thinking”—wondering about alternative ways past events could have happened. Unlucky people dwelled on ways things could have gone better, while lucky people felt gratitude that things hadn’t gone worse—in essence, lucky people practiced Holiday’s suggestion to focus only on the upside of any negative situation.
Specifically, Wiseman asked subjects to imagine that they were at a bank during a robbery and wound up getting shot in the arm. While unlucky people labeled this as an unlucky situation, mourning that they happened to be in the bank when this crime occurred, lucky people classified this as a lucky situation, noting that they could have easily been shot in the head and feeling grateful that they survived. By comparing situations to worse alternatives, they were able to recontextualize any situation into something positive, proving Holiday’s assertion that every situation carries some benefit.
Wiseman found that this “downward counterfactual thinking” not only makes lucky people feel happier about their lives, but it also makes them more optimistic, and consequently, more receptive to future opportunities. Wiseman asked subjects to count the number of photographs in a newspaper, but he placed a large note on the second page that gave the answer away. The lucky people, who approached the task in a relaxed, open way, were much more likely to see the note than unlucky people, who were too focused on the job they were given to see the opportunity staring them in the face.
This illustrates in greater detail how a pessimist overwhelmed by negative events may falsely conclude that they’re trapped by circumstance, as Holiday describes—your perspective limits the opportunities you see. In contrast, Wiseman’s lucky subjects, primed to take advantage of positive opportunities, were more likely to stumble into romantic success and promotions at work. As Holiday would predict, their optimistic perceptions determined how they responded to life events, even problems, making their lives demonstrably “luckier.”
In Holiday’s eyes, we have a moral obligation to live as virtuous a life as possible. A virtuous person, by Holiday’s definition, is someone who honestly works to improve their life and the lives of others as much as possible. With this in mind, he argues that pursuing virtue is the most fulfilling thing you can do with your life. Holiday asserts that virtuous action can and should be our source of pride—the motivating energy that makes us happy to be alive.
To this end, the ability to find opportunities within a problem is necessary to live a virtuous life. When you see obstacles as opportunities, they lose the power to upset you or diminish your motivation to live virtuously. In contrast, whenever you fail to see the opportunity in any problem, you have an excuse not to act. According to Holiday, we’ve all used these excuses at some point to avoid our responsibility to live virtuously. In doing so, we deprive ourselves of the forward momentum necessary to live a good life.
Holiday argues that even if your current task seems insignificant in the grand scheme of things, or you end up failing miserably, the long-term pursuit of virtue will fulfill you. If you’re constantly trying your hardest to improve the lives of yourself and others, every task is meaningful.
The Benefits of Living Virtuously
Holiday expands on why he believes a life of virtue is so important in his book Stillness Is the Key, the third in his trilogy on Stoic philosophy. While he reiterates that morally, we should live our lives as virtuously as possible, he focuses more on the fact that virtue benefits the one practicing it.
While Holiday expresses in The Obstacle Is the Way that you need the ability to see the opportunities within problems to live virtuously, in Stillness Is the Key he emphasizes the reverse: Living virtuously ensures that you’ll see opportunities in any situation. When you define success as a virtuous life, you’ll never be stuck or disappointed, because there’s always an opportunity to practice virtue.
A life without virtue is stressful, unfulfilling, and exhausting, as every decision requires you to calculate possible outcomes and fear you won’t get what you want. In contrast, making your decisions based on virtue gives you peace, as practicing virtue is fulfilling in itself, even if things don’t turn out the way you hoped. Virtue pays off the most in difficult moments—you can be certain and feel proud about living virtuously when there’s nothing else to feel certain or proud about.
In every situation or obstacle, there are hidden opportunities that you can turn to your own benefit. Finding them is a matter of viewing the obstacle neutrally (seeing it as it is, without judgment), then reorienting your thinking to see it as a gift rather than a problem.
Describe a problem or challenge that frustrated you this week. Why was it frustrating?
Try describing it again, this time as objectively as possible. Remove all emotion and judgment—merely state the facts as if reading a news article. (For example, you might reframe “My friend is giving me the cold shoulder for no reason” as “Three of my texts were left unanswered, and I feel offended.”) How does this differ from your first description?
What potential benefits can you see in the situation? How can you take advantage of them? (In our example, you could use these unanswered texts as an opportunity to discuss and resolve long-standing issues with your friend.)
So far, we’ve established that Stoics view everything that happens as neither intrinsically good nor bad—instead, they believe that you determine whether something will positively or negatively impact your life depending on how you perceive the situation. Additionally, we’ve discussed how Holiday believes that your ultimate purpose should be to improve your life and the lives of others, and positively interpreting the events in your life will give you the strength to overcome obstacles on your way to this goal.
For the rest of this guide, we’ll be discussing specific strategies to help you accomplish this: ways to reorient your thinking and seize the opportunities within your obstacles. In this part, “The Internal Fight,” we’ll focus on Holiday’s internal, emotional strategies for success. These tips will help you avoid becoming demoralized by external events and keep you motivated to pursue your life purpose. (In the book, Holiday refers to this practice as “The Discipline of Will.”)
Stoic philosophers emphasize the importance of emotional regulation—intentionally deciding which emotions you will allow to influence your behavior. Holiday argues that this is a practical skill that everyone can (and must) learn.
It’s a simple fact of life: You will frequently feel emotions (such as fear and anger) that work against you and push you away from your goals. If you don’t exert control over these unhelpful emotions, you’ll sabotage yourself before you’ve even begun to take action.
Holiday makes it clear: This doesn’t mean you aren’t allowed to have feelings. It’s likely impossible to suppress every negative feeling you have. Give yourself time to feel whatever emotions naturally arise. However, also work toward an emotional state that motivates you to act. It’s okay to feel any emotion. It’s not okay to let your emotions prevent you from doing what’s right. For example, if your coworker angers and embarrasses you by deliberately pointing out your mistake in front of the boss, give yourself a minute to calm down, then continue to work as best you can.
Additionally, Holiday emphasizes that your emotional state is completely under your control. It can’t be weakened or stopped by any external forces. This makes emotional regulation one of the most powerful tools you have at your disposal.
Eupatheiai: The Only Good Emotions
Holiday’s stance on emotion regulation is less extreme than the original Stoic teachings. Holiday sees negative feelings as more or less an inevitable part of life, defining “The Discipline of Will” as the ability to act despite your unhelpful emotions. On the other hand, traditional Stoics believed that by exerting your rationality, you can learn to completely cleanse yourself of harmful emotions. They saw all negative emotions as a failure of rationality and argued that by exercising logic, you would realize that you had nothing to be upset about. Like Holiday, they emphasized that everyone has the power—and obligation—to control their emotional state.
In fact, traditional Stoics believed virtuous people should only feel three emotions: the three eupatheiai, or “good states.” These were chara, boulêsis, and eulabeia, commonly translated as joy, wish, and caution. “Joy” is the rational judgment about something good in the present, “wish” is the rational judgment about something good in the future, and “caution” is the rational judgment about something bad in the future.
The Stoics denied the idea that anything could be rationally judged as bad in the present. Since they believed in logos, a rational power bringing order to the universe, they maintained that everything in the present was good, unfolding according to its fate.
Here are some tactics you can use to conquer the negative emotions keeping you from living a fulfilling, virtuous life:
Let’s investigate each of these strategies in turn:
Holiday claims that by slowing down and analyzing your situation logically, you can soothe unhelpful, impulsive emotions like panic or anger. All it takes is a rational eye to see that no event is necessarily bad, as we discussed earlier. Every unhelpful emotion you have indicates that you’re not seeing things clearly enough.
Holiday argues that our initial emotional reactions are based on unrealistic expectations. These expectations are the only thing making you upset. If you compare what has happened to what you think “should have” happened, you’ll be constantly dissatisfied—an unhelpful emotion that does nothing but demotivate you. Alternatively, if you logically come to terms with the fact that we live in an uncertain world and there will always be unforeseeable setbacks of some kind, these events will have less of an impact on your emotional state.
To practice using logic to manage your emotions, Holiday suggests adopting this habit: Whenever you feel yourself being tugged around by your emotions, stop and interview yourself to discover why you feel the way you do. Ask yourself questions, then answer them logically. Holiday sees unhelpful emotions as the root of every problem you think you have, and you can overcome them by clarifying what irrational beliefs are making you feel this way and replacing them with a logical counterargument.
Holiday offers another mental trick to help if you’re having trouble being objective about a situation you’re involved in: Pretend the situation is happening, not to you, but to someone you know. Think of what you’d advise them to do. When you don’t personally identify with a problem, it becomes easier to solve, as your own excuses and biases no longer get in the way.
Think It Through, but Don’t Ruminate
In Emotional Intelligence, Daniel Goleman concurs with Holiday that much of the time, our negative emotions are caused by unrealistic assumptions. He also agrees that slowing down and challenging these assumptions with logic is often a good way to defuse strong emotions. However, Goleman offers a caveat to this advice, noting that it’s important not to slow down too much—thinking over an emotion for too long may extend and intensify your negative feelings.
Goleman asserts that this kind of rumination is a particularly common risk when you’re trying to combat sadness—even if you’re following Holiday’s advice. According to Goleman, we feel sad when we lack or have lost something important to us. With this definition in mind, Holiday would recommend adjusting your unrealistic expectations of what you need to be happy—becoming comfortable with what you lack instead of mourning what you think you “should” have. However, Goleman would temper this advice and warn that if you’re constantly reminding yourself to be happy with what you lack, frequently thinking about it may make you sadder.
Similarly, mental exercises such as Holiday’s self-interview and objective reframing may make you sadder by forcing you to dwell on whatever is making you sad: Self-interview requires you to “talk” with yourself at length about the thing that’s making you sad, while even pretending a sad event happened to your friend forces you to think about that event. Instead, Goleman recommends intentionally planning pleasant distractions to combat sadness. Evidence shows that sad people gravitate toward activities that are more likely to make them sadder, so it’s important to force yourself to do something that will actually lift your spirits: For example, watch comforting TV, draw a hot bath, or exercise.
Alternatively, Goleman recommends engineering a small victory for yourself, something to be proud of: For instance, organize your closet, finish a book, or buy a gift for a friend.
While slow, logical reasoning will help take the edge off many of your unhelpful emotions, it’s unlikely they’ll go away completely. In this case, Holiday recommends you transform your emotions into a form that serves you. In particular, when unfair circumstances or pointless constraints frustrate you, Holiday suggests you use that anger as fuel instead of allowing it to make you reckless.
Anger is a double-edged sword—while it gives you energy and motivation to accomplish your goals, it can also push you to take impulsive actions that end up doing you harm. Holiday argues that the way around this dilemma is to use your calm, rational mind to decide where to commit your energy, then allow yourself to act wildly and impulsively within that context. For example, a frustrated painter may act calmly and deliberately when marketing their art and deliberately choose to channel all their anger regarding their career into explosive emotion on the canvas.
Sublimation: Does Science Back It Up?
The process Holiday describes here—using your unhelpful emotions to motivate constructive action—is known in psychology as sublimation. Sigmund Freud introduced this concept into the public vocabulary. Although the majority of Freud’s hypotheses have been discredited, the concepts of sublimation and similar psychological defense mechanisms have endured.
Psychologists have conducted little empirical research on the subject of sublimation. However, one notable study found a correlation between suppressed anger and creative success, as Holiday would have predicted. Experimenters tasked a group of Protestants with making art in various media, including sculptures, poetry, and collages, to see whether Protestants engaged in sublimation more than people from other religious groups. A panel of judges rated the experimental group’s artwork as markedly better than a control group when they were either forced to suppress feelings of anger or prompted to feel “unacceptable” sexual desires. This result shows that people are capable of sublimating unwanted emotions into productive pursuits, as Holiday recommends.
The previous two strategies we’ve discussed to manage your emotions work well for short bursts of discipline. However, Holiday argues that to live a virtuous life, you need something far more powerful than temporary strength of will: You need resilience woven into your DNA as a permanent feature of your character. The Stoics called it the “Inner Citadel”—a secure space you build within yourself that’s invulnerable to any external stress.
Holiday points out that most modern people don’t have this kind of long-term resilience because our powerful technology lulls us into thinking we can control everything that happens around us—we forget that life is unpredictable. As a result, this lifestyle built around comfort is fragile. When things inevitably fall apart, we’re likely to become emotional wrecks and may give up on pursuing a virtuous life. Long-term strength of character allows us to conquer and ultimately find happiness in a world of disorder and uncertainty.
Holiday asserts that it’s possible to build this kind of emotional strength with practice over time. Decide where you need to go and resolve that you will do anything it takes to get there, no matter what obstacles get in your way—then do it again.
A More Pleasant Path to Resilience
Holiday’s advice on how to cultivate perseverance can be boiled down to “Toughen up and do it.” On the other hand, in Grit, Angela Duckworth advocates for a gentler path to resilience, one that doesn’t require as much sheer willpower.
Duckworth defines “grit” as the intersection of perseverance and passion—it’s applying Holiday’s concept of long-term resilience to a specific, consistent goal. People with grit can weather a great amount of pain to achieve their purpose. Developing grit, however, is easier than just muscling through the pain, as Holiday makes it out to be. Instead, Duckworth asserts that you can develop grit in stages, initially pursuing something fun that interests and gratifies you, then practicing to achieve superiority, and finally merging your skill with an altruistic purpose. In other words, resilience develops naturally as you pursue satisfying goals.
Duckworth would argue that once you reach this stage of purpose and mastery, you won’t even want to live the fragile life of technology-swaddled comfort Holiday warns about. You’ll be instinctively drawn to big selfless goals and will derive pleasure from overcoming challenges. In contrast to the Stoic ethos of “rationality over passion,” Duckworth frames the path to resilience as the natural blossoming of innate human potential.
Holiday argues that the best way to tackle any fearsome problem or obstacle is to break it down and just focus on finishing one step at a time. Do the first step well, then move on to the next step and the next. Don’t think about the end goal, just what you have to do now. Holiday insists that there’s no problem too big to solve when broken down into discrete to-do items.
Holiday asserts that breaking a problem down into steps has a number of benefits: First, when you have a plan to follow, problems feel less daunting—each step is a psychologically manageable task that you can work up the courage to complete. Second, a step-by-step process prevents you from feeling lost or getting distracted. It points you in the right direction and ensures you’re continuously making progress. Lastly, a specific plan reminds you that it's up to you, and only you, to take action.
Crossing the Desert: This Requires Faith
In Eat That Frog!, Brian Tracy illustrates this same step-by-step strategy with an anecdote: Over a thousand people a year die traveling through the Tanezrouft, one of the most desolate areas of the Sahara desert, because blowing sand obscures the trail, causing travelers to get lost. To solve this problem, French colonists placed large black barrels every five kilometers along the trail, allowing Tracy himself to cross the deadly plain by focusing on reaching one barrel at a time.
With this illustration, Tracy highlights an insight that’s missing from Holiday’s discussion of the step-by-step strategy: When a task reaches a certain size, it becomes impossible to plan out the entire process ahead of time. When your plan involves unknown variables or complex moving parts, the only thing you can do is take the first step and have faith that the next step will reveal itself to you.
The benefits of a step-by-step plan outlined by Holiday still apply in this modified approach: A short-term to-do item will still feel manageable, even if you don’t know where it will lead. Second, as long as you have a single goal to move toward, you won’t feel lost. Lastly, a way to move forward into the unknown forces you to stay accountable by preventing you from using the excuse of an uncertain process to avoid moving toward your goal.
Building up your tolerance for long-term hardship and taking things step-by-step are helpful strategies to conquer obstacles over a long period. Zooming out to an even longer timeframe, Holiday’s next two strategies involve sources of motivation intended to power you through an infinite number of obstacles.
The first such source of motivation is the satisfaction of helping others. Holiday argues that working to solve the problems of others is one of the most effective ways to solve our own problems.
Holiday notes that in challenging times, we tend to narrow our perspective and focus on ourselves, desperate to find a way to escape pain and fear. But our instincts of self-preservation sabotage us by making it more difficult to see events objectively. When we’re only looking out for ourselves, we interpret everything that happens as good or bad for us instead of neutral, as they really are. As we’ve previously established, these subjective judgments cause the majority of our suffering.
On the other hand, Holiday asserts that by turning our attention outward and helping others, we can tap into an unlimited source of motivation and strength. Active service to others will renew you with a sense of purpose and self-worth, and you can seize this greater purpose anytime, anywhere. Negative emotions like anxiety and self-pity fade away when you discover a way to move forward and do good.
Helping Others Unconditionally Is the Key to Happiness
While Holiday frames the feeling of contribution to others as a source of motivation to achieve your virtuous goals, in The Courage to Be Disliked, Ichiro Kishimi and Fumitake Koga make the more extreme argument that these feelings of contribution are the essence of all happiness. However, they add the caveat: You need to help others unconditionally to be happy, asking nothing in return—not even gratitude.
Kishimi and Koga assert that happiness is based on self-worth—whether or not you think you’re a “good person.” They argue that most people base their self-worth on external approval, using the praise of others as evidence that they’re “good” enough. For example, a child builds self-worth by getting good grades to earn their parents’ approval, then grows up and gets a fancy corporate job to earn the approval of their larger culture.
However, Kishimi and Koga argue that this reliance on the approval of others is ultimately unfulfilling. If you need people to recognize how good you are, you’ll inevitably be unhappy whenever you’re denied this recognition.
Holiday makes the point that worrying only about yourself hurts you by making it difficult to see events neutrally. Kishimi and Koga would agree, arguing that by seeking recognition, you’re only concerned about yourself even when you’re helping others. Even if you spend your entire life doing good, you won’t be happy if you’re doing it for external approval.
Kishimi and Koga conclude that to find lasting happiness, you need to base your self-worth on contributing to the world in the way you think is best, even if no one approves or appreciates your actions. When you do this, people with different values—perhaps even family members—will dislike you, but to be happy, you need to work up the courage to be disliked.
Holiday’s final strategy to master your emotions, and, as we’ll see, a major source of motivation, is to accept things for what they are. He explains that Stoics divide everything in the world into two categories: what is in our control and what is outside our control. Some aspects of life are impossible to change—for instance, the actions of others, or a tragedy that has already happened. Holding an emotional grudge against a reality you can’t change will only make it more difficult to achieve your goals. Instead, peaceably accept things for what they are.
This isn’t the same as giving up—Holiday makes it clear that accepting something that’s impossible to change doesn’t require losing hope. On the contrary, it’s only after accepting the constraints you’re given that you can channel your energy and attention into alternative ways to achieve your goals. There are always paths leading forward, but you won’t be able to see them if you refuse to abandon dead ends.
You don’t have to like something to accept it—just face facts. Holiday insists that once you do so, you’ll often be able to embrace their upsides. By accepting constraints as a fact of life, you can use them to become a better person. Once-disheartening roadblocks may push you to develop new skills or teach you valuable lessons for the future.
Accepting Unhelpful Thoughts
In The Happiness Trap, Russ Harris explains how readers can use something called “Acceptance and Commitment Therapy,” or “ACT,” to find happiness in their lives. Harris uses the same rationale as Holiday to support his advice: We should focus on what we can control and peaceably accept whatever is out of our control. Harris, however, gets more specific than Holiday, applying this logic to negative thoughts. Just as Holiday suggests you accept unpleasant constraints you can’t change and focus on paths leading forward, Harris suggests you accept thoughts that don’t serve you and focus on thoughts that do.
Harris explains that by recognizing that negative thoughts are merely words and images that may or may not reflect reality, you’ll no longer see them as threats or mandates. Instead, you’ll see them as suggestions, some helpful, some unhelpful. If a negative thought pushes you toward something you can change, it’s helpful, and you should act on it. If it pushes you toward something you can’t change, you need to accept it and ignore it.
Some negative thoughts are useful. For example, if you feel bad that you forgot your spouse’s birthday, this unpleasant feeling can motivate you to be more caring and attentive in the future. On the other hand, some negative thoughts are unhelpful. For example, thinking the vague statement “I’m a bad person” doesn’t direct you toward anything constructive. In this case, Harris recommends you make space for the feeling and allow it to pass.
This is a perfect example of Holiday’s perspective on acceptance in action: Accepting unhelpful negative thoughts doesn’t mean giving up and remaining unhappy—on the contrary, it frees you to take advantage of the negative thoughts that can help you become a happier person. In short, accepting and ignoring the things you can’t change allows you to focus your actions where they can make a difference.
Once you’ve learned to peacefully accept whatever is beyond your control, Holiday argues you should take it one step further and learn to celebrate disasters. Tragic events are inevitable, but your emotional response to them is largely under your control—why not find a way for them to make you happy? Holiday is adamant that the opportunities hidden within any tragedy are more than enough to justify gratitude and celebration.
Additionally, Holiday argues that finding and embracing the good within the bad is your ultimate source of motivation. If you claim it, no obstacle can ever wear you down. Stay upbeat in all situations—act as if anything that happens is the best thing that could have happened.
The Origin of Amor Fati: Eternal Recurrence
Holiday refers to this sentiment as amor fati, a Latin phrase meaning “love of fate.” Although the ancient Stoics Epictetus and Marcus Aurelius were the first to express the idea of celebrating everything that happens, the phrase amor fati was coined by the German philosopher Friedrich Nietzsche in his book The Gay Science (1882).
While Holiday frames amor fati primarily as a source of motivation to accomplish your goals, Nietzsche presents the idea as the guiding principle of a great life. He first arrives at the concept of amor fati through a thought experiment: the hypothetical situation of “eternal recurrence.” What if, after death, you had to live your life over again an infinite number of times in exactly the same way? Nietzsche concludes that the ideal thing to do in this situation would be to face life with amor fati—if your life is already predetermined, the only way you could improve your life is by choosing to celebrate tragedy, just as Holiday describes.
When you’re facing a situation you can’t change, the only thing you can do is accept it. Once you do so, you can very likely find some benefit. Though you don’t get what you wanted, you gain something else worth celebrating.
Describe a negative situation in your life that you can’t change (for example, being required to share a small workspace with a coworker you dislike).
What benefits can you gain from this situation? Name as many as you can think of. (For example, you might get more work done next to a coworker you dislike since you won’t want to socialize with them, and you’ll get many chances to practice dealing patiently with someone who aggravates you.)
Remember: Feeling bad about something you can’t change is pointless while appreciating benefits and opportunities feels good and motivates you to act. What steps can you take to accept this situation and remind yourself of its benefits? (For example, you could start keeping a covert list of these benefits on your desk to read whenever you feel frustrated with your coworker.)
In Part 2, we began discussing specific strategies to help you accomplish your life goals and transform the obstacles impeding these goals into opportunities that move you forward. This first set of strategies had to do with internal, emotional discipline—intentionally shaping your own emotional state to push yourself toward virtuous action and withstand potentially demoralizing setbacks.
Now, in Part 3, we’ll conclude our discussion of strategies to help you achieve your life goals with a set of strategies to overcome obstacles in the external world. Holiday refers to these strategies as “The Discipline of Action,” difficult yet rewarding paths to success that require you to transform obstacles into gifts at every turn.
(Shortform note: Whereas Holiday frames the “Discipline of Action” as the ability to do whatever it takes to get what you want, the original Stoic Discipline of Action as laid out in Epictetus’s Discourses is synonymous with a life of virtue. This distinction stems from the Stoic belief that instead of chasing your desires and goals, virtuous action, based on rational feelings of love for all mankind, is the path to fulfillment—an idea Holiday acknowledges in this book, but doesn’t dwell on.)
These strategies for external success include:
Let’s take a look at each of these new strategies:
The core of Holiday’s overall strategy for success is to start immediately and rush toward your goal as quickly and aggressively as possible. When faced with the need for action, we too often procrastinate and make excuses. On a good day, we may analyze the problem and even map out solutions, but in the end, we don’t do anything, paralyzed by uncertainty. In doing so, we ignore the fact that people succeed because they act frequently and consistently, not because they act perfectly.
Consistently putting in effort is how you build the momentum necessary to reach your goals, and momentum is more important than anything else. Take big leaps toward your goals, even if they’re risky. Holiday emphasizes the danger of stagnation—if you ever stop aggressively moving forward with as much effort as you can muster, you risk becoming soft and complacent.
Holiday states that when we take our time analyzing an obstacle, we tend to obsess over what it means to us instead of simply seeing it as it is. This makes obstacles seem bigger and more difficult to deal with than they truly are. Instead of overanalyzing what problems mean, take the first step toward solving them. For example, if you lose your job, you may get caught up in painful navel-gazing, trying to pinpoint everything you did wrong and fretting about what’ll happen to you in the future. Instead, Holiday would advise you to force yourself to live in the present and start looking for another job.
The One Thing You Should Think About
In The One Thing, Gary Keller, like Holiday, acknowledges the importance of consistent action to build momentum toward your goals over time. However, Keller emphasizes that this momentum must be focused in the right place for it to be worth your time. Holiday warns of the dangers of overthinking, but Keller would argue that if you act without first considering how to optimize your effort, underthinking can be just as harmful.
Keller argues that even if you’re aggressively taking action toward your goal, you’re wasting your time if you’re not focusing on your “One Thing”—the task that will get you to your most ambitious goal faster than anything else. To find your One Thing, Keller suggests asking yourself “What one thing can I focus on that will have the greatest impact on my overall goal?” For example, if you want to start a restaurant, your One Thing may be to perfect your signature dish—this will make it easier for you to advertise, win over investors, and retain loyal customers in the future.
Another reason to take the time to determine your One Thing is the psychological advantage this provides. Holiday warns that taking too much time analyzing your problem and what it means for you will make it seem more difficult to complete than it actually is. However, if you follow Keller’s advice, analyzing your problems may actually make them less intimidating, as the goal is to identify tasks and obstacles you can ignore completely. In Keller’s eyes, you have to do far less to succeed than people generally imagine. Paring your big goal down to the most essential task will give you the confidence to take action.
Holiday asserts that in many cases, aggressive action is most effective in times when we’d least want to act: after an unexpected disaster sweeps us off our feet. When tragedy strikes, most people recoil, taking fewer risks and seeking to conserve whatever they have left. However, we would be better off keeping our eyes open for an opportunity within the tragedy, as the harshest tragedies sometimes carry the greatest gifts.
Tragedies take something from us that we would have wanted to keep or otherwise shake us out of our comfort zone. However, Holiday points out that by changing our circumstances so drastically, they inevitably reveal new choices we wouldn’t have been able to make before the crisis. To use an extreme example, if you’re the victim of identity theft and lose your life savings, the event may spur you to pursue your dream of selling your belongings and joining a monastery.
Furthermore, Holiday cites a psychological phenomenon called post-traumatic growth—evidence shows that people who persevere through pain and suffering are often positively transformed by the experience. They recognize their own strength and become more motivated to accomplish meaningful tasks. You can claim benefits like these by continuing to act in the face of tragedy.
Why You Need Some Adversity
In The Happiness Hypothesis, Jonathan Haidt devotes a chapter to the benefits of tragedy and examines the phenomenon of post-traumatic growth. Haidt goes into greater detail than Holiday about how enduring tragedy helps you develop a resilient character, and he even makes the case that some hardship is necessary for humans to reach their full potential.
Haidt notes that trauma not only exposes survivors to new, often better opportunities (as Holiday establishes), but it also changes, and often improves, the values and priorities they use to evaluate those opportunities. When ripped from their comfort zones, trauma survivors realize that the things they used to find important—their career or material comforts—no longer matter to them. They spend time exploring alternative sources of happiness (for instance, loving relationships) and often settle on more reliable and sustainable sources of happiness than those they previously held.
Additionally, Haidt explains that adversity serves as valuable material for the narrative you tell yourself about your life. If, thinking back, your life story serves as proof that you’re the kind of person who overcomes adversity for a noble cause, you’ll be more resilient and purposeful in the present. For this reason, a certain amount of adversity is healthy, especially in your late teens and early adulthood, when your self-narrative is first solidifying.
Holiday acknowledges that if you follow his advice to act aggressively and persistently, you’ll inevitably fail often. However, he sees this as an unequivocally good thing. Trial and error is the most effective way to learn anything. Every failure teaches you how not to do something and forces you to come up with ideas you wouldn’t have normally thought of.
We’ve all heard stories of people learning valuable lessons from failure. We know that it’s a necessary part of the path to success. Yet most of us will do anything we can to avoid failure—it’s embarrassing and painful. Arguing against this attitude, Holiday points out that trial and error hurts much less than a life in which you’ve stopped learning. Prideful people who refuse to learn from their mistakes doom themselves to repeat the same misguided actions indefinitely.
It’s in your best interest to fail as soon as possible, to catch obvious mistakes before investing hundreds of hours into something destined to fail. Thus, Holiday recommends you take small, frequent risks when working toward your goals. The sooner you can expose your work to external feedback (and potential failure), the better. With every failure, investigate what went wrong and why. Then change something and try again, repeating this cycle as often as you can.
How Thinking in Bets Helps You Learn
In Thinking in Bets, professional poker player Annie Duke dispenses advice on strategic decision-making in uncertain circumstances. Like Holiday, Duke views trial and error as the most valuable learning tool available to us, and she offers specific tips on how to get the most value out of our mistakes.
Duke’s thesis is that we should view every belief we hold and decision we make as a bet—a gamble based on the idea that something might be true. Thinking in bets is helpful for two reasons: First, it forces us to acknowledge that there is always a chance we could be wrong. Instead of seeing our beliefs as either true or false, we place them on a spectrum between true and false, making us more likely to adjust them after negative outcomes.
Second, thinking in bets helps us recognize that every decision we make requires risk and potential sacrifice. Just as we lose money on a failed bet, every misguided decision we make leads us to a worse future than we could have had. For both of these reasons, imagining our beliefs and decisions as bets helps us avoid repeating the same mistakes—which, as Holiday points out, is far more painful than learning from trial and error.
Additionally, thinking in bets naturally encourages us to take small risks for frequent external feedback, as Holiday advises, since it prompts us to consider the possibility that long-term unquestioned beliefs may lead to a massive loss. For example, imagine you’re managing a PR team in charge of your company’s rebranding. If you have faith in your team, you may be tempted to invest hundreds of hours in a full redesign that will sweep your boss off their feet. If you were to think in bets, however, you would recognize that this is a costly gamble with a non-zero chance your boss won’t like it. A smaller, safer bet would be to run several design mockups by your boss, seeking feedback before investing too much time and money in the project.
Holiday asserts that people who habitually fear failure—that is, almost everyone—generally assume that they can accomplish far less than they actually can. To avoid this mistake, he advises you to confidently set unreasonably ambitious goals and attempt to do the impossible.
As we’ve established, the only way for a problem to be impossible to solve is for you to believe that it is. Holiday insists that the reverse is also true: In a sense, believing that something is possible allows you to bend widely accepted “facts” of reality. This is something that all of history’s groundbreaking artists, inventors, and activists have done—if no one attempted to do the “impossible,” the human race would never make progress. You can contribute to humanity on an unimaginably grand scale.
To Holiday, another benefit of setting your ambitions unrealistically high is that you’re raising the stakes: You’ll look like a genius if you succeed and a fool for trying if you fail. He advises you to seek out high-pressure situations like this because they’re most likely to inspire your best work. By focusing on the energizing effect of a big risk, you can transform it from something terrifying into something exciting.
Multiply Your Goals by Ten
In The 10X Rule, Grant Cardone makes the same argument as Holiday: Setting goals that seem unrealistic is the key to success. Specifically, Cardone lays out the “10X Rule”—you should set goals ten times bigger than what you think you should achieve, and expect to put in ten times as much effort as you imagine is necessary.
Counterintuitively, Cardone argues that most people fail because they don’t set difficult enough goals. How can this be? Most people set average, realistic goals and underestimate the effort it takes to achieve them. When it becomes obvious how much work these goals actually require, they aren’t excited enough to push through the unexpected struggle, so they quit.
Like Holiday, Cardone emphasizes that enormous goals have tremendous motivating power. Accomplishing something that seems impossible—getting your name in the history books, so to speak—is a dream that will make you want to put in ten times the effort you normally would. Consequently, Cardone asserts that the way to get anything you want is to frequently reflect on your “10X goals”: Write them down twice a day, phrasing them as if you’ve already accomplished them to immerse yourself in what it will feel like to succeed.
Holiday argues that it’s important to remember that eventually, things will go wrong. People will let you down and random disasters will strike—this is the only constant in our unpredictable world. Your only defense is to anticipate what could go wrong and prevent or prepare for it. Holiday recommends making this a core step of your routine: Before taking any action, think up contingency plans for everything you can imagine going wrong.
It’s unpleasant to think about all the bad things that could happen, and consequently, too few people do it. However, Holiday asserts that this delusional optimism results in countless disasters that could have easily been prevented with a little foresight—disasters with consequences that are ultimately much more painful than thinking negatively ahead of time.
Additionally, Holiday points out that when you refuse to consider negative outcomes, not only do you suffer fully avoidable consequences, but you also create a greater divide between your expectations and the world’s harsh reality. Inevitable setbacks are even more painful when you deny the possibility that they could happen. The world seems disproportionately unfair.
Stoics, on the other hand, refuse to shy away from reality. Holiday asserts that if we think Stoically, viewing all events as neither good nor bad, we have no reason to fear misfortune and can analyze it head-on. This is beneficial: Mentally preparing for adversity not only ensures that you’ll respond wisely and appropriately when the time comes, but it also means you won’t be upset since everything is happening just as you expected.
You Shouldn’t Try to Predict Everything
In The Dichotomy of Leadership, Jocko Willink and Leif Babin argue that while planning for what could go wrong (as Holiday suggests) helps avert painful disasters, overplanning—attempting to prepare a detailed response for every possible setback—can be harmful.
Trying to predict everything that could go wrong will severely slow you down, and it may even halt your progress entirely. At a certain point, this wasted time becomes more costly than it’s worth. Additionally, overpreparing for unlikely events often causes its own problems. For example, Babin, a commander in the Navy SEALs, learned that assigning more soldiers than necessary to a task endangered the mission, as the team became more difficult to manage with size.
For these reasons, Willink and Babin recommend limiting yourself to three or four contingency plans for the most likely things to go wrong, as well as a plan for your worst-case scenario.
Is It Bad to Be an Optimist?
Holiday makes the case that if you think optimistically, refusing to expect negative outcomes, life’s inevitable disappointments and frustrations will be even more painful. Recent research backs up this argument: One study of 1,601 British citizens found that optimists who predicted they would make more money in the next year than they really did reported lower well-being and greater emotional distress than realists who were able to accurately forecast how much money they would earn.
However, the same study showed that excessive pessimism—predicting things will be worse than they really are—reduces well-being even more than optimism. The researchers suspect that constantly expecting the worst keeps pessimists unhappy, even when things turn out better than they hoped. This conclusion implies that Holiday is right to promote the Stoic practice of seeing events neutrally. Ideally, you would be able to anticipate misfortune without allowing it to dampen your spirits.
Finally, Holiday advises keeping an open mind when formulating ways to achieve your goals. We often get stuck because we assume that there’s only one way to get what we want. In reality, there are an infinite number of ways to achieve success—they’re just less obvious than the first idea that comes to mind. Instead of waiting until the perfect conditions for the ideal strategy to succeed, use whatever strategy allows you to immediately move forward.
Unconventional Paths to a Life Purpose
We can apply this logic not only to specific short-term goals but also to your overarching life purpose. According to David Epstein in Range, many people assume that to achieve the highest level of success, you need to set a long-term goal years in advance and commit to reaching it no matter what. In reality, there are an infinite number of meandering ways to become a top performer without planning to do so.
One Harvard study found that, out of 50 high-level professionals from a variety of fields, 45 had followed an unconventional path to their position, believing that they were the exception to the rule. Stumbling into success isn’t an anomaly—it’s the norm. By only planning in the short term, moving forward in whatever area appeals to you at the time, you can find more success than if you limit yourself to a single predetermined life path.
According to Holiday, if your current strategy is failing, you can try:
Let’s discuss each of these unconventional tactics:
In many cases, the most successful strategy is that which is least expected. Holiday explains that the conventional strategy—the one other people in your situation use the most often—frequently has the lowest chance of success, as it’s the strategy your enemies and obstacles are the most prepared for. Using an obscure strategy to reach your goal often allows you to succeed with far less effort.
For example, if you’re trying to get your novel published, instead of sending query letters to agents or publishers and burying your pitch among thousands of others, find an unconventional way to make connections in the industry—for instance, locate a nearby writers’ conference to network at and volunteer to help run it.
When you’re working with far fewer resources than the situation seems to require (or fewer resources than your competitors have), Holiday argues that an unexpected strategy becomes a necessity. This is one of the hidden benefits of what seem to be entirely detrimental limitations—by forcing you to find effective paths to success, your constraints become unique strengths.
Acting Unpredictably Disorients Your Opponents
In The 48 Laws of Power, Holiday’s mentor Robert Greene argues that even if your unexpected strategy isn’t successful in itself, acting unpredictably is valuable because it’s one of the most intimidating strategic moves possible. Doing something unpredictable, even irrational, forces any opponents you have to consider that they may be missing something. This paranoia and confusion often cause them to make mistakes.
Greene asserts that even if you lack direct competitors to intimidate, acting unpredictably has other benefits. When no one understands why you’re doing something, you create an air of intrigue, attracting the attention of potential supporters. You may even earn their respect as people ascribe sophisticated motives to your actions that you never had.
Unlike Holiday, who emphasizes the necessity for underdogs with few resources to do what’s unexpected, Greene states that unpredictability is most powerful for established successes. Once you’ve already proven yourself to be competent, observers are more likely to assume that everything you do is deliberately calculated.
Second, Holiday asserts that sometimes, you’ll need to bend or break the rules to get what you want. Ask for forgiveness, not permission. Push the boundaries, even if it makes you uncomfortable. Holiday states that if you’re honestly pursuing your ideals, a little dishonesty in the name of the greater good is fully justified. Once you’ve found a mission that’s important and virtuous enough for you to devote your life to it, as we’ve established Holiday wants you to do, the only thing that matters is that you get it done. He points out that you’ll have a devastating advantage over your competitors who are following the rules.
When Is It Right to Break the Rules?
How do you know when bending or breaking the rules is the right thing to do? The answer to this question will vary depending on your personal values, but here’s one guiding principle: When you bend the rules, you need to be aware of what you’re sacrificing. Most constraints exist for a reason, and breaking them may have unexpected consequences.
For example, Pablo Picasso mastered the rules of traditional painting—perspective, light, and shadow—before throwing them out the window. He knew the exact effect that these techniques gave his paintings, which allowed him to intentionally achieve a specific groundbreaking effect by sacrificing them in his cubist work.
Lastly, in some cases, the best way to get results is to do nothing—especially if action isn’t getting you anywhere and is causing you to struggle through a tough situation. According to Holiday, in many situations, the harder you struggle, the worse your problems get. It’s easy to get overeager, spring into action, and end up hurting yourself. For example, a programmer who downs energy drinks to code through the night will get sloppy, leaving bugs that take a great deal of time to resolve. If they’d remained inactive, resting for a while before jumping into the project, things would likely have gone more smoothly.
At first, this push toward inaction seems to contradict Holiday’s advice to relentlessly take action and move forward. However, he clarifies that inaction can be a form of action when it’s the most effective way to move forward.
Holiday explains that to determine whether inaction is the right thing to do, be aware of how much you’re progressing toward your goals. As we’ve previously established, stagnation is one of the most common pitfalls on the way to success. With this in mind, it’s best not to jump to the conclusion that inaction is the right move if your progress thus far has been slow and you’re at risk of stagnating. But if your intense efforts to make an obstacle budge aren’t working, it’s possible you’re pushing forward too aggressively and even temporary inaction would benefit you.
It’s worth noting that if you’re passionate about a goal, doing nothing can feel more difficult than taking action. The same drive that pushes you toward your goal may itself become an obstacle, urging you into a situation you would be better off avoiding. Holiday points out that this kind of self-control requires humility—you have to admit to yourself that tackling the problem in a straightforward way isn’t working for you. After you back away from the obstacle, a new way forward is likely to reveal itself.
Iatrogenics: When It’s Better to Do Nothing
In Antifragile, Nassim Nicholas Taleb discusses this topic at length, arguing that harmful, unnecessary action causes far more problems than we imagine, in many areas of human life. This is called iatrogenics, translated as “caused by the healer”—cases in which well-intentioned intervention ends up hurting more than helping. Taleb asserts that in these situations, doing nothing would be a more constructive and moral way to move forward.
For example, Taleb argues in his book Skin in the Game that foreign intervention in distant wars inevitably prolongs the conflict and violence. He makes the case that the infamous Israeli-Palestinian conflict would have been resolved decades ago if organizations like the United Nations and the Arab League had simply chosen to do nothing. Consequently, he’s sharply critical of interventionist leaders, accusing them of lacking the humility that Holiday maintains is necessary to pursue inaction.
Holiday states that it’s important to keep tabs on whether you’re making progress toward your goal to determine whether inaction is ideal. However, Taleb points out that in environments where iatrogenics run rampant, the damage is difficult to see. Because we can’t clearly link harmful effects to their causes—such as war in the Middle East to foreign policy—harmful intervention continues.
Taleb comes to the conclusion that we need to implement systematic ways to distinguish situations that need intervention—such as large-scale environmental damage—from situations that would be better off left alone.
When making plans, consider what could go wrong in advance to prepare for or prevent problems. When you’ve anticipated a problem, you won’t be thrown off track or respond incorrectly if it comes to pass.
Describe a plan you’re making for an upcoming event—for example, for a trip, wedding, renovation project, or community event.
Next, list everything you can think of that could disrupt your plan (such as weather, illness, or a financial emergency).
For the three most likely problems, write out backup plans in the form of “if … then” scenarios (if this happens, I’ll do this). For example, if rain is forecast, we’ll move the event to the gymnasium.
How did this exercise make you feel? Can you see yourself doing it more often in your regular life?
When you’re stuck on a problem, don’t be tempted to give up. Each effort is an opportunity to test ideas and learn; eventually, you’ll find the right one.
Think of a problem where you’ve tried multiple solutions, but nothing’s worked (for example, searching for a new job). What do you think makes this problem so difficult to solve?
Why do you think your attempts so far have failed? What have you learned so far?
How might you be making the situation more difficult for yourself? What unfounded assumptions might you be making about the problem? (For example, if you’re unable to find a new job, you may be limiting yourself to jobs that are too similar to your previous position, or falsely assuming that your resumé is perfect for the kind of job you’re trying to land.)
What’s an unconventional approach you could use to solve this problem? (Remember: You might need to try something unexpected, break the rules, or do nothing. In your job search, you may take an unexpected route and look for a job in a new field, or even settle for a temp job or paid internship.)