The Obstacle is the Way by Ryan Holiday unlocks ancient Stoic wisdom for conquering life’s hurdles. This powerful guide transforms setbacks into stepping stones, offering a fresh perspective on adversity.
Dive into this review to discover how Holiday’s insights can revolutionize your approach to challenges and propel you towards success.
Table of Contents
Genres
Self-help, Philosophy, Personal Development, Business, Motivation, Success, Stoicism, Psychology, Leadership, Inspirational, Money, Career Guides, Personal Success in Business, Job Hunting, Productivity, History
The Obstacle is the Way draws from Stoic philosophy to present a practical approach to overcoming adversity. Holiday argues that obstacles are not just challenges to be endured, but opportunities for growth and advantage. The book is structured around three core disciplines: Perception, Action, and Will.
In Perception, Holiday teaches readers to view obstacles objectively, separating emotion from fact. He emphasizes the importance of maintaining a calm, rational perspective when facing difficulties.
The Action section focuses on persistent, creative problem-solving. Holiday encourages readers to take decisive action, even in the face of uncertainty or fear. He illustrates how great leaders and thinkers throughout history have used obstacles as catalysts for innovation and progress.
Will is about developing mental resilience and perseverance. Holiday emphasizes the Stoic principle of focusing only on what’s within one’s control, accepting external circumstances while maintaining inner strength.
Throughout the book, Holiday weaves historical anecdotes and modern examples to illustrate his points. From Marcus Aurelius to Steve Jobs, he shows how successful individuals have applied these principles to overcome seemingly insurmountable obstacles.
Review
The Obstacle is the Way offers a refreshing take on the self-help genre, grounding its advice in time-tested philosophical principles. Holiday’s writing style is engaging and accessible, making complex Stoic concepts relatable to modern readers.
The book’s strength lies in its practical applicability. Each chapter concludes with actionable strategies, allowing readers to immediately implement the ideas in their lives. The historical examples are well-researched and effectively illustrate the timeless nature of the book’s core principles.
However, some readers might find the repetition of certain ideas throughout the book slightly redundant. Additionally, while the Stoic approach is powerful, it may not resonate with everyone’s personal philosophy or circumstances.
Despite these minor drawbacks, The Obstacle is the Way remains a valuable resource for anyone seeking to develop resilience and turn challenges into opportunities. It’s particularly relevant for entrepreneurs, leaders, and individuals navigating periods of significant change or adversity.
Holiday’s work serves as a timely reminder that our response to obstacles often matters more than the obstacles themselves. By reframing our perception of challenges and taking purposeful action, we can indeed turn adversity to our advantage.
What’s inside?
Embrace the powerful philosophy of Stoicism to turn any obstacle to your advantage.
Recommendation
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.
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.
Take-Aways
- 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.
Summary
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.
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.
Table of Contents
Copyright Page
Contents
Preface
Introduction
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
Iterate
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
Perseverance
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
Acknowledgments
Selected Bibliography
The Stoic Reading List
Reading Recommendations