Book Summary: The Obstacle Is the Way

Table of Contents

The Book in Three Sentences

In this summary of The Obstacle Is the Way, you’ll learn concepts from stoicism, the Greek philosophy of enduring pain so that you can live a better life. By focusing on what you control, obstacles then become opportunities to thrive. Author Ryan Holiday uses examples from some of the most successful people in history to illustrate different lessons.

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The Obstacle Is the Way Summary

Preface

In the year 170, Marcus Aurelius, emperor of the Roman empire, wrote to himself that problems are expected and they can empower you. When we face a problem, we can be blocked by obstacles or we can advance over them.

Introduction

When we face an obstacle, most of us feel paralysis, fear, frustration, confusion, helplessness, depression, or anger. We blame others, but the problem is our attitude and approach. The people who thrive are those that have a framework to deal with those obstacles. Most obstacles are internal.

Overcoming obstacles involves three critical steps:

Perception: how we see the problems.
Action: our attitude towards those problems.
Will: the energy we turn into opportunities.

Obstacles are opportunities.

Part I: Perception

Perception is how we see and understand the world around us and what it all means. Perception can make us strong or weak. To see things as they are (neither good nor bad), we have to remain calm, get rid of bad perceptions, limit our passions, and filter out prejudice and fear.

The Discipline of Perception

Before being an oilman, John D. Rockefeller was a bookkeeper in Cleveland, Ohio. He was the son of an alcoholic criminal and started working at sixteen. The depression took place in 1857 and he not only accepted what happened around him but also carefully observed the events that unfolded. Rockefeller saved his money while he learned from others’ mistakes. He learned that the market was unpredictable and the only ones who could profit from it were the rational and disciplined. At 25, investors offered him half a million dollars to find the perfect oil wells to invest in. Rockefeller didn’t find anything and returned the money because the endeavor was a dead end. Twenty years later, Rockefeller controlled ninety percent of the oil market.

Instead of submitting to temptation, the American business magnate was guided by common sense. He learned to be cold. There were many people like Rockefeller, but few reacted like him. The important thing isn’t the obstacle, but how you react to it. Where one person sees crisis, another sees opportunity. We choose how we react and we choose how we feel. Everything that happens can be seen as an excuse to move forward.

When something bad happens, we should try:

To be objective.
To control emotions.
To choose to see good.
To steady our nerves.
To ignore what disturbs others.
To place things in perspective.
To revert to the present moment.
To focus on what we can control.

This is a process that relies on self-discipline and logic.

Recognize Your Power

Boxer Rubin “Hurricane” Carter was accused of a crime he didn’t commit. When he was sent to prison for triple homicide, Carter demanded not to be treated like a prisoner. Carter refused to break, feel anger, wear a uniform, eat prison food, accept visitors, and wouldn’t be touched. He spent every moment reading law, philosophy, and history books. The midweight boxer wanted to leave not only as a free and innocent man but also as a better more educated one. Nineteen years later, Carter walked out of prison and resumed his life he proved that regardless of what happens, people can’t change your reaction. Having little power doesn’t mean you’re powerless. A mistake can be seen as training. Your mind can see a situation as bad or evil, but you don’t have to agree. This is perception.

Steady Your Nerves

Ulysses S. Grant faced danger constantly and barely reacted. Nowadays, we lose our nerves for anything. We feel overwhelmed and stressed. We should steady our nerves regardless of what happens.

Control Your Emotions

Astronauts are trained in one skill more than any other: not panicking. Panicking leads to mistakes. Don’t change your plan as soon as something unexpected happens. Obstacles make us emotional, but you should keep your emotions in check. When something happens, don’t let emotions even get started. Don’t pretend your emotions don’t exist, domesticate them instead. Deal with emotions by using logic.

Practice Objectivity

Samurai Miyamoto Musashi won fights even when he was swordless. He noted the difference between observing (seeing what is there) and perceiving (seeing more than what is there).

Alter Your Perspective

Pericles was on a mission when a solar eclipse took place. His men panicked, but he remained calm. He knew that perspective was everything and that one shouldn’t fear the darkness. Fear is irrational, distracting, and debilitating. Try to see things differently so that they lose your power over you.

The two definitions of perspective:

Context: the larger picture.
Framing: a person’s unique view of the world.

Is It Up to You?

Tommy John played twenty-six seasons as a pitcher. To achieve this, he kept asking himself the same questions: “Is there are chance?” If the answer was a yes, he kept trying, when he suffered a serious injury, he tried an experimental surgery. He had a one-in-a-hundred chance to play again, but he did. He applied this lesson over and over throughout his life. John’s strength was in noticing the difference between the unlikely and the impossible. You should focus on what you can change, not what you can’t.

This is what it’s up to us:

Our emotions
Our judgments
Our creativity
Our attitude
Our perspective
Our desires
Our decisions
Our determinations

See obstacles as challenges to overcome and improve as a person.

Live in the Present Moment

Many of the biggest corporations started during economic depressions. The people behind them didn’t notice it because they were busy dealing with what they could change. Most people start projects at a disadvantage, the ones who survive, do it because they take things one day at a time. Act like an animal, focus on the present, and don’t try to guess what it all means. Forget about the past or the future, live in the present.

To do so:

Unplug
Exercise
Meditate
Get a dog
Don’t let your mind wander

Think Differently

Steve Jobs used what’s known as the “reality distortion field”, a tactic that allowed him to succeed even when it seemed impossible. He didn’t take no for an answer and he didn’t settle for mediocrity. To achieve big things, you have to be unrealistic sometimes.

Finding the Opportunity

To avoid the war in the trenches in World War II, the Germans came up with the Blitzkrieg, a tactic where they concentrated attacks that caught their opponents off guard. This strategy seemed invincible until the Allies found its weakness. They allowed the German army to go ahead and attacked it from the sides, encircling the enemy. Obstacles can be seen as opportunities.

Prepare to Act

The worst thing that can happen isn’t the problem itself, but the problem and losing your head. Keep a clear head and then act.

Part II: Action

To dismantle obstacles, do it one action at a time. We have to be deliberate, bold, and persistent. Action is the cure to our problems.

The Discipline of Action

Demosthenes is considered one of history’s greatest orators, but it wasn’t always that way. He was born sick, lost his father at a young age, and was deprived of all the money he inherited which left him with no education. Demosthenes came up with his own exercises to improve his speech, he practiced endlessly, and he educated himself. He soon became the “voice of Athens”. His response to problems was action.

Greet your obstacles with energy, persistence, a coherent and deliberate process, iteration and resilience, pragmatism, strategic vision, craftiness, and an eye for opportunity.

Get Moving

Amelia Earhart wanted to be an aviator, but in the 1920s people saw women as weak. She agreed to be the first female in a transatlantic flight even though the proposition said she wouldn’t fly, she’d be accompanied by two men who’d be paid more than her, and she’d be in danger. She agreed to do something she didn’t want to so that she’d eventually succeed. To achieve anything, you have to start. Courage is about taking action.

Practice Persistence

General Ulysses S. Grant had trouble making a dent in Vicksburg, a strategic location on the Mississippi River. He tried different tactics but nothing worked, so he left all the supplies behind, infiltrated enemy territory, and lived off the land. Grant defied reason because he wouldn’t accept defeat. Persistence is a great asset. When you exhaust all options, try something new. Genius is persistence in disguise.

Iterate

Startups in Silicon Valley start with the “minimum viable product” or MVP, a prototype to test how consumers respond. MVP embraces failure. Failure can be good.

Follow the process

Head coach of the Alabama Football Team, Nick Saban owes his success to The Process. Instead of focusing on the important goals, you break them down into smaller pieces, you focus on the now. The Process paves the way, it relaxes you, it’s manageable, and it’s organized. When you focus on smaller victories, rather than the larger goal, everything seems connected and nothing is too ambitious.

Do Your Job, Do It Right

President James Garfield paid for college by working as a janitor. In a year, he became a professor. At twenty-six, he was the dean. Whatever it is that you do, do it well. Action should be your priority and then vanity goes away. All jobs matter, no matter how inconsequential they might seem.

What’s Right Is What Works

Two American fruit companies were fighting over land in South America because two locals allegedly owned it. One company used lawyers to do research, and the other bought the land and settled the dispute. Forget about perfection, you don’t have to follow the rules all the time. Figure things out with what you have at your disposal now. Be pragmatic.

In Praise of the Flank Attack

George Washington had a small army that was weak and undertrained. He implemented the “hit and run” tactic, attacking the enemy when it was least prepared. Washington always had a way out because he picked his battles. It wasn’t glamorous and not how people remember Washington, but it was effective. You don’t always have to go through the front door.

Use Obstacles against Themselves

Gandhi didn’t take part in the independence of India, he refused to act, making the British Empire impatient. To overcome obstacles, sometimes you have to withdraw and use their attacks against themselves. In his non-action, Gandhi was acting. By ignoring something, you attract more of it. You can look for another way out when you have a problem. Using obstacles against themselves isn’t the same as doing nothing. Passive resistance is active: it requires discipline, fearlessness, and strategizing.

Channel Your Energy

Tennis player Arthur Ashe didn’t react to anything that happened on the court. His emotions showed in his playstyle instead and he became unbeatable. He was free inside. Don’t act out, just act.

Seize the Offensive

In 2008, Barack Obama’s presidential candidacy ran into some problems because of his pastor’s remarks. Instead of ignoring these issues, Obama turn them into a speech called “A More Perfect Union”. This transformative moment led to a successful campaign where he won the elections. Move forward when there are opportunities and amid disaster, use disruptive events to your advantage.

Prepare for None of It to Work

We can’t control the world around us. You can, though, control your perception and your actions.

Part III: Will

Will is internal power that’s unaffected by the outside world. Will power is when you turn a negative into a positive.

The Discipline of the Will

Abraham Lincoln suffered from depression. He almost committed suicide on two different occasions. Lincoln grew up in poverty, lost his mother as a child, and educated himself. He thought his depression made him stronger since he felt better prepared for the problems ahead. You can find greater purpose in suffering.

Build the Inner Citadel

Theodore Roosevelt had to deal with asthma from a young age. His father built him a gym and Roosevelt worked out daily for five years. Later on, he suffered personal losses, was defeated in elections, and survived assassination attempts. Fortify yourself for the challenges ahead, both physically and mentally. Don’t take the path of least resistance, face the unknown, and turn your weaknesses into strengths.

Anticipation (Thinking Negatively)

There’s a technique called Premortem, a medical term that can be applied to a number of projects. The idea is to think in hindsight so that you can try to foresee how bad you’re going to do. This helps you come up with backup plans. Things will go wrong yet the worst thing that can happen is when something goes wrong and you didn’t anticipate it.

The Art of Acquiescence

Thomas Jefferson was born with a speech impediment. He was a bad public speaker, but he accepted it and he invested in his writing. He ended up writing the declaration of Independence. Constraints can be good. When you lose something, appreciate what you have. Someone or something can always change your plans. Be aware of it.

Love Everything that Happens: Amor Fati

When Thomas Edison was sixty-seven, his lab burned down. Edison told his son to get his mother because they’ll never see a fire like that again. Edison was excited. That’s the only acceptable reaction because he couldn’t do anything else. Soon, Edison’s lab was up and running again. Accept what’s beyond your control. Use the energy you have where it’ll have the most impact. Sometimes cheerfulness is an acceptable reaction.

Perseverance

After ten years of war, Odysseus went back home to Ithaca, but the trip took him ten more years. He faced cyclops, whirlpools, and Poseidon. But he arrived safely thanks to creativity, discipline, courage, and perseverance. In the end, the only thing that can stop perseverance is death.

Something Bigger than Yourself

James Stockdale, a Navy fighter pilot was shot down in Vietnam in 1965. Despite falling into enemy territory, he focused on his mission. He was captured, tortured, and threatened, but he didn’t give in. Instead of focusing on himself, he focused on others, and by doing so, his own suffering diminished. A shared purpose makes you stronger. Don’t make yourself so important. Try to talk less in the first person. Put others ahead of you.

Meditate on Your Mortality

In 1569, Michel de Montaigne was pronounced dead after falling from a galloping horse. He soon came to and eventually became one of the most famous European writers. Death inspired him, gave him a purpose, and made him fearless. Anyone can meditate on death. Remember you’re mortal, it gives you perspective and urgency. Death is a universal obstacle.

Prepare to Start Again

Once an obstacle is surmounted, gone, or solved, there’s another one around the corner. This is the spice of life, it gives you opportunities. Obstacles make you better.

Final thoughts: The Obstacle Becomes the Way

Near his death, Marcus Aurelius was told his friend Avidius Cassius rebelled. He waited patiently, hoping he would change his mind. He ordered his troops to capture Cassius and forgave him.

See clearly
Act correctly
Endure and accept the world as it is