The Obstacle Is the Way: Takeaways and Key Points Book Summary

When faced with obstacles, people often up and run. They change their path or give up on their goals because of what stands in their way. Challenges have always cropped up; they are not a new concept. The wisest people use obstacles to their advantage.

The words of Roman Emperor and philosopher Marcus Aurelius highlight a truth any high achiever has lived by, obstacles are opportunities in disguise. “The Obstacles in the Way” provides a recipe to follow so anyone can triumph in the face of adversity. The stories of great inventors, entrepreneurs and pioneers of their time who overcame obstacles are analyzed so anyone can emulate their success.

Obstacles are unavoidable, they’re part of everyday life - a physical injury, a redundancy, another company poaching your clients. Instead of running away from these, we have to learn to live alongside them. We have to learn to stop letting them destroy our dreams, and instead use them to help us succeed.

Holiday’s book is a guide for this. It discusses three changes we must make to conquer our goals in the face of adversity: being objective rather than subjective, using obstacle’s weaknesses, and maintaining strong will.

Key Takeaways from "The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph" by Ryan Holiday

Turn Obstacles Into Advantages
How many times did you give up on something because of an obstacle that made you either change direction or give up on your focus entirely? Obstacles occur in every aspect of daily life and should be tackled head on, turned into advantages instead of excuses, and used as a stepping stone to success. How? By focusing on the following 3 things:

Perception -Instead of thinking an obstacle is hindering or blocking a plan, that nothing ever goes your way and that this cannot be overcome, drop the emotion and look at the obstacle from an objective point of view. See it in a positive light and you'll see hidden possibilities and opportunities. When the going gets tough, remember that the largest obstacles hide the largest weaknesses. Use the strength of that obstacle against it until you weaken it so much that it crumbles.

Action- Panic never helped anyone, instead, you need to summon all of your self-discipline. With persistence and tenacity as well as by being flexible and creative you can overcome any obstacle. Sometimes you get through one obstacle to find another standing in your way, in this case, don't focus on the outcome but instead on completing each challenge individually – A mountain is climbed 1 step at a time, not all at once!

Will – You need enough willpower and belief in yourself to persevere and eventually overcome the obstacle without giving up but you must also understand and accept what cannot be changed and what can be changed. You cannot change external factors such as natural disasters, death, or other people's action. You can change the internal factor; how you react to an event or situation.

In-Depth Lessons

Lesson #1. Perception, Action and Will

Obstacles often trigger the flight or fight response. We are terrified of these things standing in our way. But, how can we turn these obstacles into building blocks?

Perception, action and will.

First, perception. If we form a positive mindset when facing obstacles, they can help us to reach our goal.

Take Warren Buffett, an American investor. He said to be “fearful when others are greedy, and greedy when others are fearful”. During the financial crisis of 2007-2008, Buffett bought stocks. Buffett made billions in a time when many people lost everything. He also helped many American firms during this difficult time by investing in them.

So, perception needs to change. Is this all? No. Our actions must also change.

Combining creativity with flexibility is the key. Mary Jackson did this. She wanted to become an engineer, but to do this she, an African American woman, had to attend an all-white school. Jackson petitioned the City of Hampton to allow her to attend, and in 1958 she became NASA’s first black female engineer. By 1979, she held the most senior title within her department.

So, we begin to perceive obstacles as tools. We alter our actions to tackle them, rather than run away from them. Next, we use will to overcome them.

We take a deeper look into these concepts in the following sections. Let’s start with perception.

Lesson #2. Perception Through Objectivity

Take a moment to reflect. Do you sulk when faced with obstacles? Do you divert your path? Run away? We need to face them head on, but through an objective lens, not our usual subjective one. We need to see the silver lining.

Take Christopher Reeve, an American actor. In 1995 he injured his spinal cord, leaving him paralysed from the neck down. After being close to death, he returned to creative work, directing and acting in a number of films and TV series. He wrote two books, and set up the Christopher and Dana Reeve Foundation, helping others with physical disability. He received a BAFTA, a Screen Actors Guild Award, an Emmy, and a Grammy. He didn’t let his physical disability take away his goals.

We achieve this perspective by taking a step back. Remove the subjectivity of personal circumstances, and enter an objective frame-of-mind. Ask yourself: what advice do you give your friends when they’re facing obstacles? Do you follow your own advice when facing your own?

A fundamental Buddhist belief is faith in man’s ability to overcome life’s challenges.

Nichiren, a 13th century Buddhist monk, taught Soka Gakkai. “Faith for overcoming obstacles” is one of the guidelines in this branch of Buddhism. The chant “Namu Myōhō Renge Kyō” enables Buddhists to take a step back into subjectivity; it renews their belief that they can overcome any challenge they face.

What is the main obstacle for positive perception? Uncontrolled Emotions.

Our initial feelings towards an obstacle are generally counterproductive. We become blinded by the anxiety and frustration, so we cannot see the potential for growth. We are subjective, not objective.

Turning obstacles into building blocks requires mastery of our emotions.
We take a moment, and compose ourselves.

Have you heard of the Gimli Glider of 1983? This was a Canadian passenger flight traveling from Montreal to Edmonton that ran out of fuel mid-flight. It would have been so easy for the pilots to panic. But instead, they focused on landing the plane safely. They successfully completed an emergency landing on a motor racing track in Gimli, Manitoba. If they had been subjective, preoccupied with the danger of the situation, they may not have survived.

They mastered their emotions. How can we do this?

Preparedness is key. If we think about the potential risks and obstacles beforehand, we cannot be surprised. We cannot be phased.

Think about the US Marine Corps. Would they send their Marines into battle with no preparation? They undergo vigorous training to prepare them both physically and mentally. By doing this, they know what to expect. They are better equipped to overcome any obstacles they face.

Our emotions can work against us. We must take a step back, gain composure, and make a disadvantage work in our advantage.

When we first encounter obstacles, we think of them as a massive fallen boulder blocking our path. We consider them immovable, and find a different route. However, what if changing our perspective allowed us to move the boulder?

Obstacles can give us tunnel vision. We only see the obstacle. We need to think about the wider context instead. This change in perspective helps to move the boulder.

Benjamin Franklin left school by the age of 10 to work. Whilst working, he taught himself grammar, rhetoric and logic, as well as maths. He used his money earnt to buy books on philosophy, electricity, physics, chemistry, meteorology and oceanography. As a result of his own investment in his education, he became a writer, printer, politician, scientist, inventor, diplomat, and more. Changing his perspective opened doors for him. It moved the boulder.
Changing your mindset can do the same.

Viktor Frankl, a Holocaust survivor, wrote about whether to “submit to those powers which threaten to rob you”, or decide something different for yourself. He chose to focus on the acts of kindness from his fellow victims, of the generosity, humanity, and dignity they showed, even in the face of the daily horrors they experienced. This positive mindset helped him to survive.

Lesson #3. Action: Sticking With It

Altering perspective has a big impact. But we also need to alter our actions. When facing obstacles, we need discipline. We need to persevere with our actions to move through the obstacle and reach our goal.

Albert Einstein faced numerous obstacles. He didn’t speak before the age of 3 and struggled to understand the rigidity of the teaching style in school. He began recognising problems in our beliefs in physics, and came up with ways to solve them. He faced scepticism for his ideas, but through endurance, his advancements became highly recognised. In his lifetime, he founded the theory of relativity, and published more than 300 scientific papers and over 150 non-scientific works.

Similarly to Einstein, J. K. Rowling conquered adversity. Rowling, author of the Harry Potter books, found herself jobless and divorced in 1993. She had no money and a child to raise on her own. She suffered from severe depression. In 1995, the Harry Potter script was rejected by 12 publishers. She persevered, and a year later the script was published by a small publisher. She has now sold over 400 million copies worldwide, and is recognised as the most successful female author in the UK.

It is this determination to succeed that separates the wheat from the chaff. It determines whether you achieve your goals, or fail to beat the obstacles.

Now, with big goals, obstacles often appear incessantly. Every step of the way you face a challenge. Focusing on each individual moment and the overall process can help you to overcome these never-ending obstacles.

Take Shawn Carter (Jay-Z), an American rapper and songwriter. He came from a disadvantaged Brooklyn neighborhood. He wanted to become a rapper, but no record label would sign him. So, he focused on the individual moment. He created his own music label, which allowed him to release his music. He gained popularity, and now has an estimated net worth of $500 million. He took advantage of the challenges, and made them into an opportunity.

You can also achieve this by focusing on the overall process, not on the goal.

For example, if your goal is to run a marathon, focus instead on running 5 hours this week. Then maybe the following week, increase this to 7 hours. This breaks it down, allowing you to focus on the process, not be blindsided by the seemingly insurmountable goal.

This is how your actions can assist you in overcoming obstacles.

Let’s return to the boulder analogy. The larger the boulder, the more difficult to move. But, does it have an area of weakness that you can exploit?

Take the myth of David and Goliath. David was up against a well-armed, trained warrior giant. Not a likely win. Goliath had a sword and shield, David a sling and some stones. Goliath charged at David, but David found a weak spot in Goliath’s armor and slung a stone there. It hit him in the head, knocking him out, and David won.

Alternately, how can you use the boulder’s weight against it?

A modern-day David and Goliath story is the Dunkirk evacuation of WWII. After the Battle of Dunkirk, over 300,000 allied soldiers were trapped there by the German army. Bizarrely, German commanders didn’t order an attack. This gave Churchill an opportunity to send all ships and boats to Dunkirk to evacuate the troops. 338,000 allied troops were evacuated. It was a miracle that they lived to fight again.

You see, by utilizing the obstacle’s strength to your advantage, it can be conquered.
The difficulty arises when facing obstacle after obstacle.

Lesson #4. Using Our Will for Change

The last piece of the puzzle to overcome our obstacles is our will. We cannot achieve anything, especially not our most desired goals, if we cannot trust and believe in ourselves.

We need our will to steer our perception and action in the right direction. We must see the obstacle objectively, turn the negative into a positive, and use our will to believe we can overcome it.

In Buddhism, they talk about inner and outer obstacles. Inner obstacles are challenges from within ourselves. Outer obstacles are those presented by the external world. There are things we can change, and things we can’t. The sooner we accept that, the easier it will be to defeat the challenges.

We use our will to change the internal obstacles, such as our negative mindset and actions, and face the external obstacles.

Franklin Roosevelt is a primary example of this. At 39 years old, he contracted polio and became paralysed from the waist down. This was an external obstacle. He very nearly gave up, but he challenged his internal obstacles. He continued to pursue his political career, winning the governorship of New York. He focused on combating the fractured economy from the stock market crash in 1929, and then the Great Depression, to gain presidency. Still today, Roosevelt is an inspiration to many people.

Embracing the external obstacles and questioning the internal obstacles allows us to overcome all challenges, both from outside and within.

By controlling our will in this way, we can confront any obstacle. This takes self-discipline.

Elon Musk achieved his billion-dollar net worth through self-discipline and sacrifice. He started up one of his first businesses in the 1990s, with little savings and no fixed salary. Because he knew he would encounter numerous pricey obstacles, he gave himself a daily food allowance of $1.

Sometimes, to achieve something great, we must silence our own needs.

Gandhi believed that “a certain degree of physical harmony and comfort is necessary, but above that level, it becomes a hindrance instead of a help”. Extended fasting was one example of his self-discipline. Gandhi deprived himself of food for 21 days in order to heal the Hindu-Muslim relationship. Through his will, Gandhi managed to unite a shattered nation.



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The Obstacle Is the Way Chapters

Chapter One - The Discipline of Perception
Chapter Two - Recognize Your Power
Chapter Three - Steady Your Nerves
Chapter Four - Control Your Emotions
Chapter Five - Practice Objectivity
Chapter Six - Alter Your Perspective
Chapter Seven - Is It Up to You?
Chapter Eight - Live in the Present Moment
Chapter Nine - Think Differently
Chapter Ten - Finding the Opportunity
Chapter Eleven - Prepare to Act
Chapter Twelve - The Discipline of Action
Chapter Thirteen - Get Moving
Chapter Fourteen - Practice Persistence
Chapter Fifteen - Iterate
Chapter Sixteen - Follow the Process
Chapter Seventeen - Do Your Job, Do it Right
Chapter Eighteen - What's Right is what Works
Chapter Nineteen - In Praise of the Flank Attack
Chapter Twenty - Use Obstacles against Themselves
Chapter Twenty-One - Channel Your Energy
Chapter Twenty-Two - Seize the Offensive
Chapter Twenty-Three - Prepare for None of it to Work
Chapter Twenty-Four - The Discipline of the Will
Chapter Twenty-Five - Build Your Inner Citadel
Chapter Twenty-Six - Anticipation (Thinking Negatively)
Chapter Twenty-Seven - The Art of Acquiesence
Chapter Twenty-Eight - Love Everything that Happens: Amor Fati
Chapter Twenty-Nine - Perseverance
Chapter Thirty - Something Bigger Than Yourself
Chapter Thirty-One - Meditate on Your Mortality
Chapter Thirty-Two - Prepare to Start Again

* Key Sources: Amazon, The Obstacle Is the Way: Summary Review


Best Quotes from The Obstacle Is the Way

“There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.”

“Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.”

“Think progress, not perfection.”

“We forget: In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given.”

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

“Focus on the moment, not the monsters that may or may not be up ahead.”

“Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well.”

“If an emotion can't change the condition or the situation you're dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one. But it's what I feel. Right, no one said anything about not feeling it. No one said you can't even cry. Forget "manliness." If you need to take a moment, by all means, go ahead. Real strength lies in the control or, as Nassim Taleb put it, the domestication of one's emotions, not in pretending they don't exist.”

“Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. Just because other people say that something is hopeless or crazy or broken to pieces doesn’t mean it is. We decide what story to tell ourselves.”

“Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.”

“For all species other than us humans, things just are what they are. Our problem is that we’re always trying to figure out what things mean—why things are the way they are. As though the why matters. Emerson put it best: “We cannot spend the day in explanation.” Don’t waste time on false constructs.”

“The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves.”

― Ryan Holiday - The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph


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Tal Gur is a location independent entrepreneur, author, and impact investor. After trading his daily grind for a life of his own daring design, he spent a decade pursuing 100 major life goals around the globe. His most recent book and bestseller, The Art of Fully Living - 1 Man, 10 Years, 100 Life Goals Around the World, has set the stage for his new mission: elevating society to its abundance potential.


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Tal Gur is a location independent entrepreneur, author, and impact investor. After trading his daily grind for a life of his own daring design, he spent a decade pursuing 100 major life goals around the globe. His most recent book and bestseller, The Art of Fully Living - 1 Man, 10 Years, 100 Life Goals Around the World, has set the stage for his new mission: elevating society to its abundance potential.

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