The Obstacle Is The Way by Ryan Holiday: Summary

The Obstacle Is The Way by Ryan Holiday: Summary
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The Premise of the book is to look at problems in a different way. We have no control over what happens to us, but we can control how we react to it. The Obstacle Is The Way is a formula for optimism. A formula for thriving not just in spite of whatever happens, but because of it. The book is divided into three main parts: Perception, Action, and Will.


Our attitude and approach to life’s problems determine our Perception. It’s how you look at things you can either let obstacles break you or you can find an opportunity in the obstacle. Perspective is everything.

George Clooney spent his initial years in Hollywood getting rejected at auditions. He wanted the producers and directors to like him, but they didn’t and it hurt him. He would blame the system for failing to see how good he was, and that didn’t get him anywhere.

Everything changed for him when he had a new perspective. He was going to be someone with something special to offer. He was going to be the man for the job. He was going to be the answer to their prayers and not the other way around, and that’s when it started working for him.

The difference between the right and wrong perspective is everything.

Tommy John was one of baseball’s most durable pitchers and played 26 seasons. He was a man who didn’t give up when met with adversity, he would exhaust every single resource until he was absolutely sure.

Is there a chance? Do I have a shot? Is there something I can do? This was his mantra. This first came into light during the middle of the 1974 season when he blew out his pitching arm, Up until this point when a pitcher blew out his arm that was the end of his career.

John didn’t accept that, he asked doctors if there was anything they could do that would get him back on the field. The doctors suggested an experimental surgery; the procedure is now famously known as the Tommy John Surgery.

There was a one in one hundred chance of him coming back, and he took it. He would later go on to win 164 games for the next 13 seasons.

He would later muster that same courage when his son had a horrific fall from a third-story window, swallowed his tongue and nearly died. The doctors convinced the boy wouldn’t survive but john wouldn’t give up until there was absolutely nothing they could do. Sure enough, his son made a full recovery.

Rubin “Hurricane” Carter was a top contender in the middleweight division in the 1960s. He was at the height of his boxing career when he was wrongly accused of a crime that he did not commit: triple homicide. Here’s his story and how he reacted to it.

He turned his prison sentence into a workshop where he transformed himself. A calmer head always prevails and a clearer head makes for steady hands.


We can take action and have control over our responsibilities and get better or let life take control over us. Once you start attacking an obstacle persist and resist. Persist in your efforts and resist giving in to temptations and distractions.

Taking Action is not going to be easy. Your first attempts are not going to work. It’s going to take a lot out of you, and even that might not be enough. Stop looking for angels and start looking for angles.

That first step can make all the difference. Take Action work on it and you’ll get closer to your goals.

“We must all either wear out or rust out, every one of us. My choice is to wear out.”


Excellence is a matter of steps followed one after the other. The unordered mind loses track of what’s in front of it and gets distracted by thoughts of the future. The process is a set of small deliberate actions that keeps our perceptions in check and our actions in sync.

Follow the process: “Don’t place much emphasis on the end result. Let’s think about what we can do today, the task at hand.”

Nick Saban

Arthur Ashe was a tennis player who was a contradiction to his contemporaries. He never overreacted, never got upset at missed shots, and never threw any temper tantrums. You can’t be serious. But that’s how he conducted himself on the tennis court.

He was physically loose and mentally tight. He had control over his emotions and he channeled that energy and took action where it mattered, on the court. He made the kind of shots that made other players gasp.


Certain things in life will cut you open like a knife. When that happens, the world gets a glimpse of what’s truly inside you. Will you curl up and give up? Or will you exercise will and get up and fight? Will is our internal power, which can never be affected by the outside world.

Abraham Lincoln Battled crippling depression that nearly drove him to suicide on two separate occasions. His life was defined by enduring and transcending great difficulty.

He grew up in rural poverty, lost his mother while he was still a child, had to educate himself, teach himself the law, then just as things were turning good his fiancé died, had a nervous breakdown, and lost in 8 elections.

This too shall pass was Lincoln’s favorite saying. He developed a strong inner fortress that got him through life’s obstacles. People are not born with an iron spine they develop it when faced with trials and tribulations. We have to forge that part ourselves.

One line that really got to me was we don’t get to control what happens to us, but we can control how we react to it.

Amor Fati – Love everything that happens.

At age 67, Thomas Edison was returning home from work, and a man came rushing into his house with urgent news.

A fire had destroyed Edison’s laboratory and his lifetime’s work.

He looked at his son who was devastated and said go get your mother and all her friends they’ll never see a fire like this ever again.

He didn’t crumble under adversity. He didn’t get angry; he didn’t quit; he didn’t feel sorry for himself.

He accepted the situation for what it is and then went to work the next day.

Despite a loss of 1 million dollars, Edison would make nearly 10 million dollars that same year.

He recovered and replied to the Obstacle in spectacular fashion.

Something that we can learn from and implement now with COVID-19 and everything that’s going on.

See it for what it is and do the best you can.

During the good times, we need to strengthen our minds and bodies so that during the difficult times we can depend on them to protect us. No one is born a gladiator, No one is born with an inner fortress. To be great at something takes practice.

We need to see obstacles as opportunities to practice some virtue: patience, courage, and creativity. Perceive things as they are, leave no option unexplored, and do the best to change what you can.

What Stands in the way becomes the way. The Obstacle is the way.


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