Book Summary: The Obstacle is the Way by Ryan Holiday

Are you looking for a book summary of The Obstacle is the Way by Ryan Holiday? You have come to the right place.

I jotted down a few key insights from Ryan Holiday’s book after reading it.

You do not have to read the entire book if you don’t have time. This book summary provides an overview of everything you can learn from it.

Let’s get started without further ado.

In this The Obstacle is the Way: The Timeless Art of Turning Trials Into Triumph book summary, I’m going to cover the following topics:

What is The Obstacle is the Way About?

Ryan Holiday brings the wisdom of Stoic philosophy up to date in his book The Obstacle is the Way. Holiday shows that while obstacles could not stop historical figures of inspiring resilience, they thrived precisely because the obstacles presented themselves. 

In both our business and personal lives, Holiday teaches us how we can turn obstacles into opportunities.

Who is the Author of The Obstacle is the Way?

Author of the best-selling book Trust Me I’m Lying, Ryan Holiday is a media strategist at American Apparel and its director of marketing. YouTube, Twitter, and Google use his media strategies for case studies.

Who is The Obstacle is the Way For?

It is not for everyone to read The Obstacle is the Way. If you are one of the following types of people, it may be right for you:

  • Anyone who works for a business during tough economic times
  • Anyone working at a start-up face great challenges to succeed
  • Anyone who would like to learn how to cope better with hardships

The Obstacle is the Way Book Summary


Many people lose faith in their path when they encounter obstacles. When they encounter an obstacle, they believe that they must completely alter their plans or give up. However, the human race has faced obstacles since the dawn of time, and some of the greatest minds in history have thought of ways to cope with everyday struggles.

Throughout their lives, they found that obstacles will inevitably arise, whether it’s a disagreeable boss who stifles our aspirations for promotion, or a precarious economic climate that makes it difficult to find employment. Instead of avoiding them, we must use them to our advantage and turn them into conditions for success instead of avoiding them. This book shows us how.

You’ll learn about a famous figure who practiced public speaking with pebbles in his mouth in order to fight for his inheritance in these chapters!

You’ll also learn what Thomas Edison did when his million-dollar laboratory burned down, destroying all his latest prototypes.

Last but not least, you’ll learn how NASA prepares its astronauts to overcome life-threatening obstacles.

Lesson 1: We can turn obstacles to our advantage by understanding them, taking action, and being willing

Most of us are angry, fearful, and frustrated when faced with an obstacle. We think it will hamper our progress and derail our plans. Yet obstacles can actually become opportunities, leading us to success instead of limiting us.

Three things must be done in order to turn an obstacle into an advantage.

The first thing we need to consider is how we perceive the obstacle. Seeing an obstacle in the right light allows us to see hidden opportunities we can utilize.

The oil baron John D. Rockefeller was successful because of this. When a financial crisis struck in 1857, Rockefeller, then 18 years old, observed people panicking and what they did wrong. When Rockefeller analyzed their failures, he was able to see the obstacle, the Panic, in a new light. 

The crisis allowed him to see the advantages it offered, act on them, and become one of the richest men in the world as a result.

Perception alone, however, is not sufficient. Taking the right action is also important when you are facing an obstacle.

When creativity and flexibility are combined, the right action is born. Women were not allowed to be pilots in those days, so Amelia Earhart struggled to become a great pilot at the beginning of the 20th century. To survive, she took a mundane job, but she kept searching for creative ways to achieve her dream.

In one call, she learned that someone was funding the first female transatlantic flight, but only as an unpaid passenger. Despite the fact that this was far from what she wanted to accomplish, she accepted – and this paved the way for an amazing career as an aviator.

We use our will to persevere until we are able to overcome the obstacle after identifying the best way to perceive it and the best action to take.

Each of these will be examined in more detail in the following chapters – starting with perception.

Lesson 2: We must learn to see obstacles objectively in order to perceive obstacles clearly

How do you respond to an obstacle? Is the world against you, and do things always go against you? It would be more effective if you took a step back, viewed the situation objectively, and wondered, “How can I turn this obstacle into an advantage?”

We can even turn the biggest obstacles to our advantage if we view them in this way.

Rubin “Hurricane” Carter, a celebrated boxer from the 1960s, was falsely accused of a triple murder and sentenced to death. Although he was in prison, he resolved to not let his circumstances overwhelm him, and instead thought of how he could make the most of the situation.

As a first step, he vowed not to accept the injustice, but to continue fighting for justice through the courts. By using his time indoors to study history, philosophy, and law, he made the most of his limited physical freedom. 

As a result of his case being overturned, Carter was eventually released after 19 years. Carter was released free and clear. In addition, he used the time to improve himself and his education.

What are the steps to achieving this objective perspective?

To step back from your highly subjective view of the situation and to learn to detach yourself from it. Imagine you are giving advice to a friend about how to overcome the obstacle. How would you respond? How would you let them proceed?

Alternatively, you can follow the Stoics, a group of ancient Greek philosophers. Their imaginations would conjure up the reaction of a sage – someone with perfect wisdom – to an obstacle. In this way, they would discover wisdom they didn’t know they possessed.

Lesson 3: Utterly uncontrollable emotions cloud our judgment and perception

In response to an obstacle, we are usually angry, frustrated, anxious and confused. However, while such emotional outbursts are natural, they actually make dealing with obstacles more difficult because they prevent us from judging the situation objectively and actually alter our perspective. We must control our emotions if we want to turn our obstacles into successes.

We can control our emotions by calming our nerves.

Civil War general Ulysses S. Grant is a famous role model for steely nerves. When he nearly died while being photographed by Matthew Brady, he was being photographed by a famous photographer. Brady had an assistant open the studio’s skylight because there wasn’t enough light for the photo. 

Grant was sitting right next to where large glass shards fell when the assistant accidently broke the window. While the shards shattered around Grant, he didn’t flinch and sat calmly in his chair instead of panicking and jumping from it. He controlled his emotions so he didn’t harm himself.

What is the best way to gain control over our emotions?

In any situation, we should prepare for what could go wrong. By doing this, we can remain calm no matter what changes occur externally.

NASA has realized the importance of this. One of the leading causes of potentially life-threatening mistakes in outer space is a panicking astronaut. That’s why NASA trains its astronauts to automatically react to obstacles until they become accustomed to them. If anything goes wrong with the initial plan, this will allow them to deal with the stress.

Whenever we are emotionally affected by obstacles, our judgment is clouded and we cannot turn them to our advantage.

Lesson 4: We can see the hidden benefits of obstacles with a malleable perspective

Obstacles usually seem insurmountable to us when we are faced with them. However, if we can change our perspective, we can discover the advantages hidden beneath the surface of an obstacle.

By considering the larger context. If we look at the obstacle in isolation, it may seem impenetrable, but if we put it into context, it is not as daunting as it first appears.

Pericles and his men were suddenly struck with darkness by a solar eclipse when they set out to battle during the Ancient Greek Peloponnesian War. Seeing this as a bad omen, many soldiers became fearful of the upcoming battle.

Pericles, however, was undaunted by this situation and used it to his advantage to motivate his troops. One of his soldiers was placed under a dark shroud, and he asked him if he was afraid. Fortunately, the soldier didn’t seem to be afraid. 

Pericles asks why they should be deterred from fighting because of yet another cause of darkness. As a result, the soldiers saw the eclipse in a new light, becoming more enthused for battle.

Obstacles can also be turned into advantages through perspective.

As a young actor, George Clooney learned this lesson. He struggled to get a role when he first arrived in Hollywood. Director, producer, and casting agents were upset with him because he didn’t recognize their talent.

In the end, his perspective changed. Film producers had to find the right actor, not him. They were the ones who needed to find the right actor, not him. As a result, Clooney decided to imagine himself as the actor the company was looking for. 

He believed that he would get the job if he stood out as the answer to the obstacle they faced. As a result of changing his perspective, Clooney was able to turn what had initially seemed like an obstacle into his first step toward success.

In the following chapters, we will find out how to overcome the many obstacles of life.

Lesson 5: Effective action requires persistence and discipline

Changing perspectives is important, but it’s not enough on its own – we need to take action, too. When faced with the many obstacles that separate us from true happiness, it takes more than one act – it takes the strict discipline to act, and to keep acting until the obstacle is overcome.

Demosthenes, the greatest orator of ancient Athens, proved that discipline wins out over all.

Demosthenes was a sickly and frail person with a speech impediment and was cheated out of his inheritance by his guardians. Despite all these obstacles, he did not give up. As a result, he devised a strategy and followed it with incredible discipline. 

So he could bring his former guardians to justice, he taught himself law in his study. His speech was improved by repeatedly reciting oratory with a mouthful of pebbles!

Demosthenes not only won his trial against his ex-guardians, but also became the most famous orator in Athens because of his persistence.

Thomas Edison understood that persistence is necessary for effective action just like Demosthenes.

The filament (a bamboo piece) for Edison’s incandescent light bulb took 6,000 different types of material to find. The incandescent bulb was invented by other inventors at the same time, but no other inventor went through so many tests to ensure they got it. Edison’s great success can be attributed to his persistence and tenacity.

Lesson 6: Focusing on each moment and the process as a whole helps us accomplish our goals

Suppose you’re involved in a long-term project, and no matter how persistently you work, obstacles seem to keep appearing. How should you proceed? You should focus on the moment and the overall process instead of the goal.

Why is that?

Thus, we can better handle the tasks at hand, increasing our chances of long-term success.

Here are two highly successful companies that were both created during extremely challenging economic times.

Walt Disney Company was founded eleven months before the market crash of 1929. The IT company, Hewlett-Packard, was founded in 1935 during the Great Depression. Both companies succeeded by not letting economic problems overshadow their day-to-day activities. 

They kept focused on the present moment, rather than focusing on the overwhelming goal of becoming successful during the recession. The companies grew step by step and eventually became the world-famous ones we know today.

This can be viewed another way, as each moment is part of the overall process that leads toward the goal. It is this paradigm that helps professional sport coaches turn what might seem like an impossible task into the regular, single steps necessary to achieve success.

The head coach of the University of Alabama American football team, Nick Saban, teaches his players the importance of following the process. Rather than thinking about winning the championship, Saban advises his players to perform well in each game and play their best in each game. In this way, his players are able to focus on the goal without being distracted by all the “obstacles” such as defeats or injuries.

To take the right action, one must focus on the whole process and live within each moment of that process.

Lesson 7: We can turn obstacles in our favor by identifying their weaknesses

You will sometimes be faced with an obstacle so big that you will think you cannot overcome it. However, the biggest obstacles often hide the biggest weaknesses.

The Salt March, for example, demonstrates how great power can be used against itself. Gandhi’s civil disobedience – the non-violent movement known as satyagraha – is a prime example.

To demonstrate how unjust Britain’s military rule was, Gandhi used non-violence and symbolic acts. His Salt March led hundreds of thousands of Indians to collect salt from the ocean in direct violation of British laws prohibiting unregulated salt collection. In addition, as it was a non-violent endeavor, it did not engage in any combat. 

By challenging the empire non-violently he showed how weak it really was, despite its monopoly of violence.

Utilizing an obstacle’s strengths against it is another way to exploit its weaknesses.

When Alexander the Great tamed Bucephalus, his wild horse, he did this. Bucephalus refused to allow anyone to ride him until Alexander softened him, and he would fight anyone who attempted to do so furiously. Bucephalus ran in a straight line until it became exhausted and gave up fighting. Alexander steered and controlled the stallion after mounting him. 

By exploiting the horse’s obvious weakness (its constant anger consumed the horse’s energy), Alexander was able to tame Bucephalus, using his strength in riding (his endurance).

It is possible to overcome even the strongest obstacle if you use its strengths against it.

We will learn how to keep persisting despite constant obstacles in the following chapters.

Lesson 8: We can change what we can and accept what we cannot change through our will

Perception – the ability to observe something objectively – and action (the ability to transform our obstacles into advantages) are not sufficient on their own. There is one last ingredient: our will. Until we believe in ourselves and apply this internal power to every action we take, we cannot overcome obstacles.

When we act and perceive with the will, we are able to recognize and change those things within our control and not be preoccupied with things beyond our control. 

Stoic philosophers, such as Epictetus, Seneca and Marcus Aurelius, developed this philosophy in ancient Athens and Rome. By asking themselves what they could control and what they could not, they focused their will. In their view, external factors are beyond our control. 

The inevitability of death, natural events, other people’s actions, etc., is one of them. Yet they believed that internal factors could be changed. This includes our attitudes, judgments, responses, and decisions.

We can then use this knowledge to change our internal obstacles – i.e., our will – yet still face and accept the external obstacles we will inevitably face.

In Thomas Edison’s reaction to a devastating blow to his career, this principle is embodied. A fire broke out at Edison’s research and production facility when he was 67 years old. The entire building, including all Edison’s prototypes, papers, and research, was on fire when he arrived on the scene.

This event didn’t faze Edison, who saw it as a chance to start over. In the end, he realized he could not turn back time, but he could change his perspective and approach a seemingly insurmountable obstacle as a chance to start over – to get “rid of a lot of rubbish,” as he put it. Edison turned a million dollar loss into a $10 million profit by the end of the year.

Lesson 9: We can push ourselves to the limits of our mortal existence with a disciplined will

We can master our obstacles – and ourselves – if we learn to accept what we cannot change, and discipline our will to change what we can.

One of the founding texts of Western literature, Homer’s Odyssey, shows how a disciplined will allows us to persevere in the face of the most difficult obstacles. Odysseus leaves Troy after fighting for 10 years in the Odyssey

He has no idea it will take him another ten years to reach home as he faces many trials and tribulations. His journey includes being held captive, facing temptation, losing all of his men, encountering dangerous whirlpools, and even fighting off a six-headed monster and a cyclops!

How was he able to overcome all the obstacles the gods sent his way? His determination to return home.

It can also push us to the edge of human possibility by ignoring our personal circumstances in favor of more important goals. James Stockdale, a US pilot captured during the Vietnam War, illustrates this perfectly.

It was known that prisoners of war would be tortured and may even be killed. Stockdale, however, decided to be a leader for his fellow prisoners rather than give up or fear for his life. 

To make sure that all the soldiers knew they were all in it together and shouldn’t feel ashamed for providing information, Stockdale created a support system in the camp because he knew some of the tortured might become insane. 

He was able to endure years of imprisonment and torture by focusing on the greater goal of survival, so that he and others were able to survive.

Final Summary

The obstacle you meet will become the fuel that enables your success when you perceive it objectively, act against its weaknesses, and remain determined in your will to overcome it.

Further Reading

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