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Book Summary: The Obstacle is the Way – The Ancient Art of Turning Adversity to Advantage

Through the ages, people have relied on the philosophy of Stoicism to craft their daily lives, conquer their difficulties and make consequential decisions. Yet if reading the translations of 2,000-year-old texts sounds daunting, this week’s reading recommendation explains the practical applications of Stoic philosophy in lively, clear prose.

We all face adversity, but what if you looked at the roadblocks in your life as opportunities to grow? In The Obstacle is the Way, Ryan Holiday explains how you can utilize venerable Stoic principles to turn obstacles into advantages.

What’s inside?

Embrace the powerful philosophy of Stoicism to turn any obstacle to your advantage.

Book Summary: The Obstacle is the Way - The Ancient Art of Turning Adversity to Advantage


Through the ages, people have relied on the philosophy of Stoicism to conquer their difficulties. In addition to ancient Greeks and Romans, proponents included Frederick the Great, Michel de Montaigne, Thomas Jefferson, George Washington, Adam Smith and Theodore Roosevelt. Every year, former US president Bill Clinton studies the writing of Roman emperor Marcus Aurelius, a well-known Stoic philosopher. Former Chinese leader Wen Jiabao has read Marcus’s immortal Meditations “more than 100 times.” Media strategist Ryan Holiday explains how contemporary people can utilize some venerable Stoic principles to turn obstacles into advantages. His lively, clear prose brings these ancient ideas to modern life. We recommend his helpful guide to the Stoic path to leaders, entrepreneurs, and anyone facing significant challenges.

The Obstacle Is The Way By Ryan Holiday Animated Growth Mindset


  • Stoicism – an operating manual for life – is a pragmatic philosophy that helps people overcome their difficulties.
  • This venerable philosophy inspired George Washington, Thomas Jefferson, Adam Smith and Frederick the Great, as well as many contemporary leaders.
  • Stoicism rests on three primary disciplines: “perception, action and the will.”
  • Perception is the way you see the world. Viewing it realistically or with a bias can help or hinder you.
  • The right action is always directed, deliberate, bold and persistent.
  • The world can break your body, but thanks to willpower, it can never break your spirit and mind. You – not some external entity – control your will.
  • Obstacles that stand in the way of progress can actually promote progress.
  • People improve by facing and meeting challenges head-on.
  • The obstacles you overcome provide benefits you could not otherwise realize.
  • How you think about and react to obstacles while maintaining your composure defines you.


The Stoic Way

In 170 AD, Roman emperor Marcus Aurelius wrote, “Our actions may be impeded…but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.” He concluded, “The impediment to action advances action. What stands in the way becomes the way.” Marcus was a Stoic. His thoughts encapsulate the words of other illustrious Stoics: “Chrysippus, Zeno, Cleanthes, Ariston, Apollonius, Junius Rusticus, Epictetus, Seneca” and “Musonius Rufus.”

“All great victories, be they in politics, business, art or seduction, involved resolving vexing problems with…creativity, focus and daring.”

An ancient Zen parable features an almost identical line of thinking, stating: “The obstacle in the path becomes the path…Within every obstacle is an opportunity to improve our condition.”

Marcus knew about obstacles. Frequent wars were prominent throughout his 19 years as emperor, during which his realm suffered a horrible plague. He faced a meager treasury, an attempted coup, a hoggish brother-in-law, as well as toilsome travel throughout the Roman Empire – from Asia Minor to Syria, Egypt, Greece and Austria. However, he never lost his patience, grace or courage. People of his era admired Marcus as a great man and a good emperor.

“Nothing we’ll experience is likely without potential benefit.”

Stoicism and Marcus Aurelius’s wisdom motivated men and women throughout history, helping to spark the Renaissance, the Enlightenment, the Industrial Revolution, the US civil rights movement and Silicon Valley’s amazing high-technology advances.

Stoicism addresses real-life issues that confront everyone: “Are you worthy?” “Can you get past the things that inevitably fall in your way?” “Will you stand up and show…what you’re made of?”

“Focus on what is in front of you, right now. Ignore what it ‘represents’ or it ‘means’ or ‘why it happened to you’.”

Obstacles can provide benefits. First, you must move beyond typical responses to trouble, including “fear, frustration, confusion, helplessness, depression” and “anger.” Marcus Aurelius’s courage and self-knowledge enabled him to transform trouble and tragedy into triumph. Achieve similar results by adopting the vital Stoic lesson: “The obstacle is the way.”

“Man does not simply exist but always decides what his existence will be, what he will become the next moment.” (Holocaust survivor Viktor Frankl)

Marcus defined the methods to overcome obstacles: “Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance – now at this very moment – of all external events. That’s all you need.”

“Contingent Disciplines”

To act wisely, develop these perspectives:

1. The Discipline of “Perception”
How you see the world provides meaning to the events of your life. Don’t assign “good or bad” labels to events. Put aside your fears and prejudices. See things for what they are. See the truth, not a biased interpretation of it.

“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.” (former Intel CEO Andy Grove)

Here are some tenets and examples of the power of perception:

  • “Alter your perspective” – The American industrialist John D. Rockefeller once worked for just 50 cents a day as a bookkeeper in Cleveland, Ohio. As an investor, he rode out major national financial crises in 1857, 1873, 1907 and 1920. Where others saw catastrophe and chaos, the objective, unemotional Rockefeller saw valuable lessons and opportunities. So much so, that by 1877, his perception and his nerve helped him corner “90% of the oil market.”
  • “Recognize your power” – During the 1960s, Rubin “Hurricane” Carter was a leading middleweight title contender. Carter was unjustly convicted in a triple-homicide case. In jail, he never ceded power to the warden or guards. He maintained his independence and his identity. Carter – and not the authorities – held control over his mind and spirit. He spent his time in prison working on his legal case. After 19 years, Carter got his verdict overturned. Once released from prison, he never looked back.
  • “Steady your nerves” – During the US Civil War, General Ulysses S. Grant always seemed completely nerveless. Once, a shell exploded near him, and killed a horse right next to him. Unfazed, Grant calmly surveyed the battlefield through his field glasses. He saw that his troops were removing supplies from a steamship when it exploded. Everyone ducked for cover except Grant, who ran toward the shattered steamboat to help the survivors.
  • “Control your emotions” – NASA trained America’s first astronauts to remain cool under pressure and to avoid panic. The agency had the astronauts practice every aspect of their space flight “hundreds of times,” until the routines became commonplace. Comprehensive training eliminated the unfamiliarity of spaceflight.
  • “Is it up to you?” – Tommy John pitched in Major League Baseball for an astonishing 26 seasons. John always asked himself: “Is there a chance?” “Do I have a shot?” “Is there something I can do?” When he was 45 years old, the Yankees cut John. Unfazed, he appeared as a walk-on at the team’s next spring training. He worked hard, made the team and pitched the season opener, a win over Minnesota.
  • Lessons learned – Stay objective. When necessary, change the way you interpret what you see. Don’t agonize over the past or worry about the future. Focus your thoughts and actions on the present. Find the good in the bad. Stay bold.

2. The Discipline of “Action”

When you are deliberate, bold and persistent, you are better prepared to take “right and effective” actions. Use the “creative application” of action to dismantle obstacles, as in these examples:

  • “The voice of Athens” – When Demosthenes was young, his prospects were not favorable. He was frail and sick and suffered a major speech impediment. His guardians stole his inheritance. But nothing knocked Demosthenes off his path “to become the greatest orator of Athens.” He constantly practiced oratory, often with his mouth full of pebbles. Demosthenes practiced his speaking skills in private. When he was ready, he filed suit against his guardians to retrieve his stolen money. He prevailed in his legal battle, thanks to his stirring oratory. Demosthenes became the voice of Athens, promoting the philosophy, “Action, action, action!”
  • “Get moving” – Amelia Earhart’s goal was to become an accomplished pilot. In her time, the 1920s, women were supposed to be dainty, even feeble. Someone proposed that Earhart participate in “the first female transatlantic flight.” She wouldn’t fly the plane; a man would. She accepted this embarrassing offer, but a few years later, she became the first woman to “fly solo nonstop across the Atlantic.”
  • “Practice persistence” – Thomas Edison tried 6,000 different filaments before he created the first incandescent light. Nikola Tesla “once sneered” at Edison’s perseverance, saying that if the inventor had to find a needle in a haystack, he would examine every straw. Edison understood that some situations demand such persistence.
  • “Follow the process” – Nick Saban, head coach of the University of Alabama’s powerhouse football team, follows what he calls “the process.” He tells his players, “Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you need to do in this drill, on this play, in this moment. That’s the process: Let’s think about what we can do today, the task at hand.” Pay attention to your process. Take things “one step at a time.”
  • “Use obstacles against themselves” – Gandhi’s fight for India’s independence was not a fight at all. The British did “all of the fighting” and “all of the losing.” Through peaceful civil disobedience, Gandhi demonstrated that action doesn’t always mean performing like an army. It can mean taking a stand and holding on to what is right.
  • Lessons learned – Set out to develop the “Minimum Viable Product,” as identified by Silicon Valley’s iterative MVP philosophy. Remember the engineering touchstone: “Failure is a feature.” Learn from every failure. Treat your job like the most important work in the world. Stay aware that sometimes a flank attack will work better than a head-on charge. Like great athletes, try to operate “in the zone” by deliberately focusing. Even so, you may not always win. If you don’t, move boldly ahead to the next task.

3. The Discipline of “Will”

The world can knock you down and break your heart. But if you harness your willpower, no knockdown blow can deter you. Your will – not anyone else’s – puts you firmly in charge of your life and accomplishments. Proper willpower is steady, not blustery. You connect to your internal power without braggadocio; the best strength of will springs from “humility, resilience and flexibility.” Examples of the power of the will include:

  • Master your will – Abraham Lincoln exemplified willpower. He grew up poor. He was for many years a failed politician, facing multiple ballot-box defeats. He suffered all his life from crippling depression, yet Lincoln had to lead the North through the bloody years of the American Civil War. Because of his incredible willpower, he never let these problems derail him or cause him to lose hope. No matter what the challenge, Lincoln endured, becoming the ideal president to head the US during its most calamitous, destructive period.
  • “Build your inner citadel” – As a young boy, Theodore Roosevelt had severe asthma. Nightly asthma attacks nearly killed him. To build stamina, he worked out daily at a personal gym that his wealthy father built in their home. His hard work paid off: By “his early 20s,” Roosevelt had fortified his body and won his life-and-death battle against asthma. He called his gutsy fight “the Strenuous Life.” Roosevelt said, “We must all either wear out or rust out: everyone of us. My choice is to wear out.”
  • “Love everything that happens” – When he was 67, fire destroyed Thomas Edison’s “research and production” facilities. His “priceless records, prototypes and research” went up in smoke. Demonstrating amazing sangfroid, Edison’s reaction was, “It’s all right. We’ve just got rid of a lot of rubbish.” Any other response – crying, shouting, smashing things – would have accomplished nothing. Edison accepted his setback with grace, with a sense of lightheartedness. When the fire struck, Edison told his son, “Get your mother and all her friends. They’ll never see a fire like this again.”
  • “Meditate on your mortality” – In 1569, French nobleman Michel de Montaigne nearly died after being thrown from a horse. In a mystical moment, he felt his life slipping away – on the “tip of his lips.” This near-death experience energized Montaigne. He became one of Europe’s most famous writers, a noted dignitary and a “confidante of the king.” He turned into an avid student of death, researching how people thought of it and what it meant in other cultures. Eventually, death betrays everyone. Use this knowledge to embrace your own mortality. In the meantime, like Montaigne, make the best use of the time you have.
  • “Prepare to start again” – As a Haitian saying holds, “Behind mountains are more mountains.” You may overcome numerous major obstacles, but that doesn’t get you off the hook. More obstacles may emerge to block your path. Accept this reality. It’s life.
  • Lessons learned – Postmortems are useful; so are pre-mortems – thinking in advance about “what could go wrong.” Sometimes you must simply acquiesce when things don’t go your way. Adopt the attitude, “C’est la vie. It’s all fine.” You are a part of the universe. Try to make your little corner of it as fulfilling as possible.

Stoicism: The Operating Manual

Across the centuries, academics in their ivory towers tried to assume ownership of philosophies such as Stoicism and tried to guard it as part of their exclusive domain. As developed by Seneca, Zeno and others, the philosophy of Stoicism was never intended to be isolated as remote, sterile intellectualization. Those sages first promulgated Stoicism as “an operating system for the difficulties and hardships of life,” and that is how it should remain.

“Don’t let the force of an impression… knock you off your feet; just say to it: Hold on a moment; let me see who you are and what you represent. Let me put you to the test.” (Epictetus)

The immortal Epictetus, who overcame bitter slavery to become a renowned Stoic philosopher, gave the title Enchiridion to his famous manual of Stoic ethical advice. Translated from the Greek, the title means “close at hand.” Epictetus and the other ancient Stoics regarded Stoicism as something “to be in your hands, to be an extension of you.” Marcus Aurelius put this concept another way: Stoicism makes people “boxers instead of fencers,” battling boldly and bravely against life’s difficulties, challenges and obstacles.

About the author

Media strategist Ryan Holiday is the former marketing director at American Apparel. His ad campaigns garnered coverage in Advertising Age, The New York Times and Fast Company.

Ryan Holiday is one of the world’s foremost thinkers and writers on ancient philosophy and its place in everyday life. He is a sought-after speaker, strategist, and the author of many bestselling books including The Obstacle Is the Way; Ego Is the Enemy; The Daily Stoic; and the #1 New York Times bestseller Stillness Is the Key. His books have been translated into over 30 languages and read by over two million people worldwide. He lives outside Austin, Texas, with his family.


Self Help, Business, Money, Career Guides, Personal Success in Business, Job Hunting, Philosophy, Personal Development, Psychology, Leadership, Productivity, History

Table of Contents

Copyright Page
Part I: Perception
The Discipline of Perception
Recognize your Power
Steady your Nerves
Control your Emotions
Practice Objectivity
Alter your Perspective
Is it up to you?
Live in the Present Moment
Think Differently
Finding The Opportunity
Prepare to Act
Part II: Act Ion
The Discipline of Action
Get Moving
Practice Persistence
Follow The Process
Do your Job, do it Right
What’s Right is what Works
In Praise of the Flank Attack
Use Obstacles Against Themselves
Channel your Energy
Seize the Offensive
Prepare for None of it to Work
Part III: Will
The Discipline of the Will
Build your Inner Citadel
Anticipation (Thinking Negatively)
The Art of Ac Quiescence
Love Everything that Happens: Amor Fati
Something Bigger Than yourself
Meditate on your Mortality
Prepare to Start Again
Final Thoughts: the Obstacle Becomes the Way
Postscript: you’re Now a Philosopher. Congratulations
Selected Bibliography
The Stoic Reading List
Reading Recommendations


#1 Wall Street Journal Bestseller

The Obstacle is the Way has become a cult classic, beloved by men and women around the world who apply its wisdom to become more successful at whatever they do.

The book’s many fans include a former governor and movie star (Arnold Schwarzenegger), a hip hop icon (LL Cool J), an Irish tennis pro (James McGee), the World Number 1 golfer (Rory McIlroy) and the coaches and players of winning teams like English Rugby National Team, the New England Patriots, Seattle Seahawks and Chicago Cubs.

The book draws its inspiration from stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. Stoics focus on the things they can control, let go of everything else, and turn every new obstacle into an opportunity to get better, stronger, tougher. As Marcus Aurelius put it nearly 2000 years ago: “The impediment to action advances action. What stands in the way becomes the way.”

Ryan Holiday shows us how some of the most successful people in history-from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs-have applied stoicism to overcome difficult or even impossible situations. Their embrace of these principles ultimately mattered more than their natural intelligence, talents, or luck.

If you’re feeling frustrated, demoralized, or stuck in a rut, this book can help you turn your problems into your biggest advantages. And along the way it will inspire you with dozens of true stories of the greats from every age and era.

“The impediment to action advances action. What stands in the way becomes the way.” – Marcus Aurelius

We are stuck, stymied, frustrated. But it needn’t be this way. There is a formula for success that’s been followed by the icons of history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—a formula that let them turn obstacles into opportunities. Faced with impossible situations, they found the astounding triumphs we all seek.

These men and women were not exceptionally brilliant, lucky, or gifted. Their success came from timeless philosophical principles laid down by a Roman emperor who struggled to articulate a method for excellence in any and all situations.

This book reveals that formula for the first time—and shows us how we can turn our own adversity into advantage.

Read an Excerpt/PDF Preview


In the year 170, at night in his tent on the front lines of the war in Germania, Marcus Aurelius, the emperor of the Roman Empire, sat down to write. Or perhaps it was before dawn at the palace in Rome. Or he stole a few seconds to himself during the games, ignoring the carnage on the floor of the Colosseum below. The exact location is not important. What matters is that this man, known today as the last of the Five Good Emperors, sat down to write.

Not to an audience or for publication but to himself, for himself. And what he wrote is undoubtedly one of history’s most effective formulas for overcoming every negative situation we may encounter in life. A formula for thriving not just in spite of whatever happens but because of it.

At that moment, he wrote only a paragraph. Only a little of it was original. Almost every thought could, in some form or another, be found in the writings of his mentors and idols. But in a scant eighty-five words Marcus Aurelius so clearly defined and articulated a timeless idea that he eclipses the great names of those who came before him: Chrysippus, Zeno, Cleanthes, Ariston, Apollonius, Junius Rusticus, Epictetus, Seneca, Musonius Rufus.

It is more than enough for us.

Our actions may be impeded . . . but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.

And then he concluded with powerful words destined for maxim.

The impediment to action advances action.

What stands in the way becomes the way.

In Marcus’s words is the secret to an art known as turning obstacles upside down. To act with “a reverse clause,” so there is always a way out or another route to get to where you need to go. So that setbacks or problems are always expected and never permanent. Making certain that what impedes us can empower us.

Coming from this particular man, these were not idle words. In his own reign of some nineteen years, he would experience nearly constant war, a horrific plague, possible infidelity, an attempt at the throne by one of his closest allies, repeated and arduous travel across the empire—from Asia Minor to Syria, Egypt, Greece, and Austria—a rapidly depleting treasury, an incompetent and greedy stepbrother as co-emperor, and on and on and on.

And from what we know, he truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity. The power he held never seemed to go to his head—neither did the stress or burden. He rarely rose to excess or anger, and never to hatred or bitterness. As Matthew Arnold, the essayist, remarked in 1863, in Marcus we find a man who held the highest and most powerful station in the world—and the universal verdict of the people around him was that he proved himself worthy of it.

It turns out that the wisdom of that short passage from Marcus Aurelius can be found in others as well, men and women who followed it like he did. In fact, it is a remarkable constant down through the ages.

One can trace the thread from those days in the decline and fall of the Roman Empire to the creative outpouring of the Renaissance to the breakthroughs of the Enlightenment. It’s seen starkly in the pioneer spirit of the American West, the perseverance of the Union cause during the Civil War, and in the bustle of the Industrial Revolution. It appeared again in the bravery of the leaders of the civil rights movement and stood tall in the prison camps of Vietnam. And today it surges in the DNA of the entrepreneurs of Silicon Valley.

This philosophic approach is the driving force of self-made men and the succor to those in positions with great responsibility or great trouble. On the battlefield or in the boardroom, across oceans and many centuries, members of every group, gender, class, cause, and business have had to confront obstacles and struggle to overcome them—learning to turn those obstacles upside down.

That struggle is the one constant in all of their lives. Knowingly or not, each individual was a part of an ancient tradition, employing it to navigate the timeless terrain of opportunities and difficulties, trial and triumph.

We are the rightful heirs to this tradition. It’s our birthright. Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?

We might not be emperors, but the world is still constantly testing us. It asks: Are you worthy? Can you get past the things that inevitably fall in your way? Will you stand up and show us what you’re made of?

Plenty of people have answered this question in the affirmative. And a rarer breed still has shown that they not only have what it takes, but they thrive and rally at every such challenge. That the challenge makes them better than if they’d never faced the adversity at all.

Now it’s your turn to see if you’re one of them, if you’ll join their company.

This book will show you the way.


This thing in front of you. This issue. This obstacle—this frustrating, unfortunate, problematic, unexpected problem preventing you from doing what you want to do. That thing you dread or secretly hope will never happen. What if it wasn’t so bad?

What if embedded inside it or inherent in it were certain benefits—benefits only for you? What would you do? What do you think most people would do?

Probably what they’ve always done, and what you are doing right now: nothing.

Let’s be honest: Most of us are paralyzed. Whatever our individual goals, most of us sit frozen before the many obstacles that lie ahead of us.

We wish it weren’t true, but it is.

What blocks us is clear. Systemic: decaying institutions, rising unemployment, skyrocketing costs of education, and technological disruption. Individual: too short, too old, too scared, too poor, too stressed, no access, no backers, no confidence. How skilled we are at cataloging what holds us back!

Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.

You know what you want to do but it feels like some invisible enemy has you boxed in, holding you down with pillows. You try to get somewhere, but something invariably blocks the path, following and thwarting each move you make. You have just enough freedom to feel like you can move; just enough to feel like it’s your fault when you can’t seem to follow through or build momentum.

We’re dissatisfied with our jobs, our relationships, our place in the world. We’re trying to get somewhere, but something stands in the way.

So we do nothing.

We blame our bosses, the economy, our politicians, other people, or we write ourselves off as failures or our goals as impossible. When really only one thing is at fault: our attitude and approach.

There have been countless lessons (and books) about achieving success, but no one ever taught us how to overcome failure, how to think about obstacles, how to treat and triumph over them, and so we are stuck. Beset on all sides, many of us are disoriented, reactive, and torn. We have no idea what to do.

On the other hand, not everyone is paralyzed. We watch in awe as some seem to turn those very obstacles, which stymie us, into launching pads for themselves. How do they do that? What’s the secret?

Even more perplexing, earlier generations faced worse problems with fewer safety nets and fewer tools. They dealt with the same obstacles we have today plus the ones they worked so hard to try to eliminate for their children and others. And yet . . . we’re still stuck.

What do these figures have that we lack? What are we missing? It’s simple: a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.

John D. Rockefeller had it—for him it was cool headedness and self-discipline. Demosthenes, the great Athenian orator, had it—for him it was a relentless drive to improve himself through action and practice. Abraham Lincoln had it—for him it was humility, endurance, and compassionate will.

There are other names you’ll see again and again in this book: Ulysses S. Grant. Thomas Edison. Margaret Thatcher. Samuel Zemurray. Amelia Earhart. Erwin Rommel. Dwight D. Eisenhower. Richard Wright. Jack Johnson. Theodore Roosevelt. Steve Jobs. James Stockdale. Laura Ingalls Wilder. Barack Obama.

Some of these men and women faced unimaginable horrors, from imprisonment to debilitating illnesses, in addition to day-to-day frustrations that were no different from ours. They dealt with the same rivalries, political headwinds, drama, resistance, conservatism, breakups, stresses, and economic calamities. Or worse.

Subjected to those pressures, these individuals were transformed. They were transformed along the lines that Andy Grove, former CEO of Intel, outlined when he described what happens to businesses in tumultuous times: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

Great individuals, like great companies, find a way to transform weakness into strength. It’s a rather amazing and even touching feat. They took what should have held them back—what in fact might be holding you back right this very second—and used it to move forward.

As it turns out, this is one thing all great men and women of history have in common. Like oxygen to a fire, obstacles became fuel for the blaze that was their ambition. Nothing could stop them, they were (and continue to be) impossible to discourage or contain. Every impediment only served to make the inferno within them burn with greater ferocity.

These were people who flipped their obstacles upside down. Who lived the words of Marcus Aurelius and followed a group which Cicero called the only “real philosophers”—the ancient Stoics—even if they’d never read them.* They had the ability to see obstacles for what they were, the ingenuity to tackle them, and the will to endure a world mostly beyond their comprehension and control.

Let’s be honest. Most of the time we don’t find ourselves in horrible situations we must simply endure. Rather, we face some minor disadvantage or get stuck with some less-than-favorable conditions. Or we’re trying to do something really hard and find ourselves outmatched, overstretched, or out of ideas. Well, the same logic applies. Turn it around. Find some benefit. Use it as fuel.

It’s simple. Simple but, of course, not easy.

This is not a book of gushing, hazy optimism. This is not a book that tells you to deny when stuff sucks or to turn the other cheek when you’ve been completely screwed over. There will be no folksy sayings or cute but utterly ineffectual proverbs.

This is also not an academic study or history of Stoicism. There is plenty written about Stoicism out there, much of it by some of the wisest and greatest thinkers who ever lived. There is no need to rewrite what they have written—go read the originals. No philosophic writing is more accessible. It feels like it was written last year, not last millennium.

But I have done my best to collect, understand, and now publish their lessons and tricks. Ancient philosophy never cared much for authorship or originality—all writers did their best to translate and explain the wisdom of the greats as it has been passed down in books, diaries, songs, poems, and stories. All of these, refined in the crucible of human experience over thousands of years.

This book will share with you their collective wisdom in order to help you accomplish the very specific and increasingly urgent goal we all share: overcoming obstacles. Mental obstacles. Physical obstacles. Emotional obstacles. Perceived obstacles.

We face them every day and our society is collectively paralyzed by this. If all this book does is make facing and dismantling such stumbling blocks a little easier, it will be enough. But my aim is higher. I want to show you the way to turn every obstacle into an advantage.

So this will be a book of ruthless pragmatism and stories from history that illustrate the arts of relentless persistence and indefatigable ingenuity. It teaches you how to get unstuck, unfucked, and unleashed. How to turn the many negative situations we encounter in our lives into positive ones—or at least to snatch whatever benefit we can from them. To steal good fortune from misfortune.

It’s not just: How can I think this is not so bad? No, it is how to will yourself to see that this must be good—an opportunity to gain a new foothold, move forward, or go in a better direction. Not “be positive” but learn to be ceaselessly creative and opportunistic.

Not: This is not so bad.

But: I can make this good.

Because it can be done. In fact, it has and is being done. Every day. That’s the power we will unlock in this book.

The Obstacles That Lie Before Us

There is an old Zen story about a king whose people had grown soft and entitled. Dissatisfied with this state of affairs, he hoped to teach them a lesson. His plan was simple: He would place a large boulder in the middle of the main road, completely blocking entry into the city. He would then hide nearby and observe their reactions.

How would they respond? Would they band together to remove it? Or would they get discouraged, quit, and return home?

With growing disappointment, the king watched as subject after subject came to this impediment and turned away. Or, at best, tried halfheartedly before giving up. Many openly complained or cursed the king or fortune or bemoaned the inconvenience, but none managed to do anything about it.

After several days, a lone peasant came along on his way into town. He did not turn away. Instead he strained and strained, trying to push it out of the way. Then an idea came to him: He scrambled into the nearby woods to find something he could use for leverage. Finally, he returned with a large branch he had crafted into a lever and deployed it to dislodge the massive rock from the road.

Beneath the rock were a purse of gold coins and a note from the king, which said:

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

What holds you back?

The Physical? Size. Race. Distance. Disability. Money.

The Mental? Fear. Uncertainty. Inexperience. Prejudice.

Perhaps people don’t take you seriously. Or you think you’re too old. Or you lack support or enough resources. Maybe laws or regulations restrict your options. Or your obligations do. Or false goals and self-doubt.

Whatever it is, here you are. Here we all are.

And . . .

These are obstacles. I get it. No one is denying that.

But run down the list of those who came before you. Athletes who were too small. Pilots whose eyesight wasn’t good enough. Dreamers ahead of their time. Members of this race or that. Dropouts and dyslexics. Bastards, immigrants, nouveaux riches, sticklers, believers, and dreamers. Or those who came from nothing or worse, from places where their very existence was threatened on a daily basis. What happened to them?

Well, far too many gave up. But a few didn’t. They took “twice as good” as a challenge. They practiced harder. Looked for shortcuts and weak spots. Discerned allies among strange faces. Got kicked around a bit. Everything was an obstacle they had to flip.

And so?

Within those obstacles was an opportunity. They seized it. They did something special because of it. We can learn from them.

Whether we’re having trouble getting a job, fighting against discrimination, running low on funds, stuck in a bad relationship, locking horns with some aggressive opponent, have an employee or student we just can’t seem to reach, or are in the middle of a creative block, we need to know that there is a way. When we meet with adversity, we can turn it to advantage, based on their example.

All great victories, be they in politics, business, art, or seduction, involved resolving vexing problems with a potent cocktail of creativity, focus, and daring. When you have a goal, obstacles are actually teaching you how to get where you want to go—carving you a path. “The Things which hurt,” Benjamin Franklin wrote, “instruct.”

Today, most of our obstacles are internal, not external. Since World War II we have lived in some of the most prosperous times in history. There are fewer armies to face, fewer fatal diseases and far more safety nets. But the world still rarely does exactly what we want.

Instead of opposing enemies, we have internal tension. We have professional frustration. We have unmet expectations. We have learned helplessness. And we still have the same overwhelming emotions humans have always had: grief, pain, loss.

Many of our problems come from having too much: rapid technological disruption, junk food, traditions that tell us the way we’re supposed to live our lives. We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest.

Our generation needs an approach for overcoming obstacles and thriving amid chaos more than ever. One that will help turn our problems on their heads, using them as canvases on which to paint master works. This flexible approach is fit for an entrepreneur or an artist, a conqueror or a coach, whether you’re a struggling writer or a sage or a hardworking soccer mom.

The Way Through Them

Objective judgment, now at this very moment.

Unselfish action, now at this very moment.

Willing acceptance—now at this very moment—of all external events.

That’s all you need.


Overcoming obstacles is a discipline of three critical steps.

It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.

It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.

It’s a simple process (but again, never easy).

We will trace the use of this process by its practitioners throughout history, business, and literature. As we look at specific examples of each step from every angle, we’ll learn to inculcate this attitude and capture its ingenuity—and by doing so discover how to create new openings wherever a door is shut.

From the stories of the practitioners we’ll learn how to handle common obstacles—whether we’re locked out or hemmed in, the kind of obstacles that have impeded people for all time—and how to apply their general approach to our lives. Because obstacles are not only to be expected but embraced.


Yes, because these obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph.

The Obstacle Is the Way.



Video and Podcast


‘Follow these precepts and you will revolutionize your life.’ – Steven Pressfield, author of The War of Art

‘A book for the bedside of every future – and current – leader in the world.’ – Robert Greene, author of The 48 Laws of Power

“The book on stoicism that’s taking the NFL by storm.” – Sports Illustrated

“The best one I’ve read. Ryan Holiday is brilliant. If I had read The Obstacle Is the Way sooner, a few things might have been different.” – Rory McIlroy, 2x PGA Champion

“Follow these precepts and you will revolutionize your life. Read this book!” -Steven Pressfield, author of The War of Art and Gates of Fire

“A book for the bedside of every future—and current—leader in the world.” – Robert Greene, author of The 48 Laws of Power and Mastery

“First came Marcus Aurelius, then Frederick the Great . . . and now there’s you. This surprising book shows you how to craft a life of wonder by embracing obstacles and challenges.” – Chris Guillebeau, author of The $100 Startup

“A very, very good book with lots of examples about people who had to overcome great obstacles to have success.” – Nick Saban, head football coach at the University of Alabama

“In this tight, engaging book, Ryan Holiday shines a bright, powerful light on the path to living and leading well. Read it, learn from it, and get cracking!” – Nancy F. Koehn, historian and leadership expert, Harvard Business School

“My life has been beset with obstacles. It takes practice (and pain) to surmount them and achieve success. Ryan’s book is a how-to guide for just that.” – James Altucher, investor and author of Choose Yourself

“Ryan Holiday has written a brilliant and engaging book, well beyond his years. . . . It is invaluable.” – Honorable Frederic Block, Judge, U.S. District Court

“Even though I was familiar with the basis for this book — the ancient philosophy of stoicism: overcoming obstacles through the practice of wisdom, courage, self-control, and mindfulness — it felt like a revelation when I read it.” – Allison K. Hill, Los Angeles Daily News

“Tremendous! Go buy every book that Ryan Holiday has written.” – John Tesh, host of national radio show Intelligence for Your Life