The Obstacle Is the Way: Summary Review & Takeaways

This is a summary review of The Obstacle Is the Way containing key details about the book.

What is The Obstacle Is the Way About?

The author draws from the philosophy of stoicism to expand the central theme of the book, which is that how we respond to obstacles is what defines us. Stoics focus on the things they can control, let go of everything else, and turn every new obstacle into an opportunity to get better, stronger, and tougher.

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The book includes stories from history that illustrate the arts of relentless persistence and indefatigable ingenuity. It teaches you how to get unstuck and unleashed. How to turn the many negative situations we encounter in our lives into positive ones - or at least to snatch whatever benefit we can from them.

Who is the Author of The Obstacle Is the Way?

Ryan Holiday is an American author, public relations strategist, bookstore owner, and host of the podcast The Daily Stoic. He is a former director of marketing for American Apparel.

What are the main summary points of The Obstacle Is the Way?

Here are some key summary points from the book:

  • What stands in the way becomes the way. Or, in other words, how we respond to obstacles is what defines us. Within every obstacle is an opportunity to improve our condition.
  • Obstacles, if handled properly, can leave us in better shape than if we had never encountered them at all. We can challenge ourselves to better ourselves through the obstacles. We can take our struggles, flip them around and use them as a chance to enhance a virtue or skillset.
  • The things which hurt instruct. All great victories, be they in business, politics, or art, involved resolving problems with a potent cocktail of creativity, focus, and daring. When you have a goal, obstacles are actually teaching you how to get where you want to go- carving you a path.
  • Success is the product of perception of our environment. Or, in other words, an individual's perspective impacts his or her success. An objective mind, which can resist temptation or excitement, no matter how seductive, no matter the situation, can succeed. We can combat the primal responses that cause us to act irrationally by cultivating discipline in perception. Discipline in perception lets you clearly see the disadvantage and proper course of action in every situation- without the pestilence of panic or fear.
  • Recognizing our power. We decide what we will make of each and every situation. We decide whether we will break or whether we'll resist. We decide whether we'll ascent or reject. No one can force us to give up or to believe something that is untrue...Our perceptions are the thing we're in complete control of.
  • Steadying our nerves and emotions. When we are met with challenges, the two most important skills are grace and poise. They allow us to keep a cool head and deploy other skills which can help solve the problem. Cultivate the skill to remain calm so the energy that would feed negativity is used on being solution-focused and fixing problems rather than reacting to them.
  • Unhelpful emotions can be deconstructed using logic which helps us figure out root causes and helps keep us grounded. When you worry, ask yourself 'What am I choosing to not see right now?' What important things are you missing because you chose worry over introspection, alertness or wisdom?
  • By being more objective and less judgmental, we take on less of a victim mindset and can deal with the situation more powerfully and steadily. For example, we can offer such great advice to our friends because we are able to analyze the situation without personal baggage.
  • Fear is debilitating, distracting, tiring and often irrational. The task is not to ignore fear, but to explain it away. Take what you're afraid of - when fear strikes you- and break it apart.
  • We choose how we'll look at things. We retain the ability to inject perspective into a situation. We can't change the obstacles themselves- that part of the equation is set-but the power of perspective can change how the obstacles appear. How we approach, view, and contextualize an obstacle, and what we tell ourselves it means, determines how daunting and trying it will be to overcome.
  • Things that are under our control include emotions, judgments, creativity, attitude, perspective, desires, decisions and determination. Focusing exclusively on what is in our power magnifies and enhances our power. But every ounce of energy directed at things we can't actually influence is wasted- self-indulgent and self-destructive. So much power- ours, and other people's is frittered away in this manner. To see an obstacle as a challenge, to make the best of it anyway is also a choice - a choice that is up to us.
  • Live more in the present moment. Avoid getting caught up in thinking about the entire situation, wishing a situation would be another type of way, but rather being mindful and in the moment. It takes active work to be mindful and in the moment. Catch your mind when it wonders - don't let it get away from you. Discard distracting thoughts.
  • You must believe in yourself and your capabilities, especially when trying to reach big goals.
  • Look for the opportunity within an obstacle. When there's a challenge we naturally assume that we are at a disadvantage but every situation is an opportunity for us to act.
  • The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this. The worst thing to occur is for us to be faced with an obstacle AND lose our composure. By not remaining mentally composed, we make the problem larger and heavier upon ourselves.
  • A clearer head makes for steadier hands. Decide to tackle what stands in your way - not because you're a gambler defying the odds but because you've calculated them and boldly embraced the risk.
  • Action needs to be taken with creative application and not brute force. Our movements and decisions define us: We must be sure to act with deliberation, boldness, and persistence. Those are the attributes of right and effective action.
  • In life it doesn't matter what happens to you or where you came from. It only matters what you do with what you've been given. And the only way you'll do something spectacular is by using it all to your advantage.
  • All the greats we admire started by saying Yes, lets go. And they usually did it in less desirable circumstances than we'll ever suffer. Many times we wait for the conditions to be the way we want them and for the situation to go our way before we act. Those who attack problems and life with the most initiative and energy usually win.
  • Practicing persistence. Genius often really is just persistence in disguise. Thomas Edison, for example, was not the only person experimenting with incandescent lights during his time. But he was the only man willing to test six thousand different filaments to get closer to his ultimate goal.
  • For the most part, lack is not the issue. We're usually skilled, knowledgeable, resourcful, and capable enough. But do we have the patience to refine our idea? The energy to beat on enough doors until we find investors or supporters? The persistence to slog through the politics and drama of working with a group?
  • Failure can be an asset if what you're trying to do is improve, learn or do something new. It's the preceding feature of nearly all successes. There's nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities.
  • When failure does come, ask: What went wrong here? What can be improved? What am I missing? This helps birth alternative ways of doing what needs to be done, ways that are often much better than we started with. Failure puts you in corners you have to think your way out. It is a source of breakthroughs.
  • People fail in small ways all the time. but they don't learn. The world is telling you something with each and every failure and action. It's feedback- giving you precise instructions on how to improve, it's trying to wake you up from your cluelessness. It's trying to teach you something. Listen.
  • Being trapped is just a position, not a fate. You get out of it by addressing and eliminating each part of that position through small, deliberate actions - not by trying to push it away with superhuman strength.
  • Everything we do matters- whether it's making smoothies while you save up money or studying for the bar- even after you already achieved the success you sought. Everything is a chance to do and be your best.
  • In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well. Right action- unselfish, dedicated, masterful, creative- that is the answer to that question. That's one way to find the meaning of life. And how to turn every obstacle into an opportunity.

What are key takeaways from The Obstacle Is the Way?

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.

What are some in-depth lessons from the book?

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.

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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?

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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.

Book details

  • Print length: 201 Pages
  • Audiobook: 6 hrs and 7 mins
  • Genre: Philosophy, Nonfiction, Self Help

What are the chapters in The Obstacle Is the Way?

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

What are good 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.”

"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." (Meaning)

― Ryan Holiday - The Obstacle Is the Way Quotes

What do critics say?

Here's what one of the prominent reviewers had to say about the book: “In this tight, engaging book, Ryan Holiday shines a bright, powerful light on the path to living and leading well. Read it, learn from it, and get cracking!” — Nancy F. Koehn, historian and leadership expert, Harvard Business School

* The summary points above have been concluded from the book and other public sources. The editor of this summary review made every effort to maintain information accuracy, including any published quotes, chapters, or takeaways

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Chief Editor

Tal Gur is an author, founder, and impact-driven entrepreneur at heart. 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 journey and most recent book, The Art of Fully Living, has led him to found Elevate Society.

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