The Obstacle Is The Way Book Summary

The Obstacle Is The Way book summary
The Obstacle Is The Way book summary

The Obstacle Is The Way Book Summary: The Obstacle Is The Way, by Ryan Holiday, uses Stoicism to deal with overcoming obstacles, and breaks it down into a 3-step process. Learn the key lessons from this book below.

Step 1: Perception

Be Objective

Things happen all the time, but perception is what determines how we see, understand, and ultimately choose to react to them. Events that happen to us, even the obstacles, shouldn’t be seen as good or bad. They just are. We add meaning to these events, and so we have the choice to see if something is positive or negative.

We tell ourselves a story about the events that happen to us, and that dictates the emotions that we feel. If we tell ourselves a story that allows ourselves to detach from the emotions, we can maintain our composure and control. That’s when we can start telling ourselves a positive story that can move ourselves towards action and empowerment, instead of despair and debilitation.

Holiday tells the story of George Clooney, who was continuously rejected by Hollywood when he was younger. Clooney’s perspective was that the system was broken and they couldn’t see how talented he really was.

However, one day he decided to switch his perspective and see things differently. Now, he saw it as the directors and producers needing a problem solved, and that he was the man for the job. He began to project that in his auditions. It wasn’t just his acting skills that he had, but he showed that he had the whole package that the directors and producers were looking for: not just on camera, but in preproduction and during promotions.

Live in the present moment

Thinking about the past and the future aren’t helpful if it is to the detriment of dealing with the present. The only thing you truly have control over is what you do right now, anything else is just wasted. When we focus on what is in our power, it magnifies and enhances our power.

Step 2: Action

Take action

To be effective, we need directed action at the greater vision. We need to stay moving in order to create momentum. That means to take risks and move, even when we are afraid and daunted.

In 1878, Thomas Edison wasn’t the only person working on filaments, but he was the only person who was willing to test thousands of different filaments. He was persistent, and willing to fail, knowing that each failure would bring him that little bit closer to success. Genius is often just persistence in disguise.

In any venture, you will fail, but the important thing is to ask yourself what went wrong and what you could improve upon the next time.

Follow the process

Nick Saban, coach of the University of Alabama football team, uses “The Process” in coaching his team: Don’t think about winning, but just what you need to do in this drill, in this play, in this moment, on the task at hand. Focus only on what you need to do right now, and do it well. Then move on to the next thing.

What’s right is what works

Samuel Zemurray was trying to acquire the same plot of land against United Fruit, another fruit company. However, two separate owners claimed ownership of the land, in two different jurisdictions. U.F. hired lawyers and commissioned studies to figure out the rightful owner. Zemurray simply bought the land twice, once from each owner.

Use obstacles against themselves

Gandhi knew that he and his people didn’t stand a chance against the might of the British Empire. So he didn’t fight, and let the British Empire do all of the fighting, and subsequently, all of the losing.

Gandhi nonviolently resisted British rule, exaggerating his weakness. With peace and weakness as a tool, Gandhi neutralized the British Empire’s huge military advantage by making it ineffective.

Prepare for none of it to work

Even with all the preceding actions, you might still fail because we can’t control the world. However, stoicism teaches us that preparing for this allows us to neutralise its effects, and frees us to act boldly and courageously.

Step 3: Will

The discipline of will

Abraham Lincoln suffered from crippling depression and nearly committed suicide, twice. However, he found meaning in enduring and overcoming great challenges, and saw them as a way to forge his character.

Love everything that happens – Amor Fati

When Thomas Edison was 67, his lab caught fire and was surely devastated. While looking on the flames, he told his son to “Go get your mother and all her friends. They’ll never see a fire like this again.”

Cheerfulness in all situations, especially the bad ones.


There are far more failures in the world due to a collapse of will than there will ever be from objectively conclusive external events.

Antonio Pigafetta, Magellan’s assistant, said that the secret to Magellan’s success was his ability to endure hunger better than the other men.

Meditate on your mortality

Everyone dies. Life is short. If we’re not getting the results that we want, then we should change the things that we’re doing.

The Obstacle is The Way Book Summary Lessons

Thank you for reading The Obstacle Is The Way Book Summary. The above book summary is just a concise summary of the lessons that I had learnt from the book. I’ve also provided a link to a PDF version of this below. To get all the points and stories covered in the full book, you should purchase the full book. 

Buy The Book: The Obstacle Is The Way (Amazon)

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