The Obstacle Is the Way by Ryan Holiday

The Obstacle Is the Way by Ryan Holiday

The Obstacle Is the Way summary

Successful people aren’t exceptionally lucky, talented, or experienced. Instead, they live by the maxim: ‘What stands in the way becomes the way.’ They learn to turn obstacles to their advantage by managing perceptions and directing actions toward the things they can change.

The Obstacle Is the Way notes & quotes

Here are my notes and quotes on The Obstacle Is the Way by Ryan Holiday. My notes are casual and include what I believe are the essential concepts, ideas, and insights from the book, along with direct quotes from the author.

  • Is there a formula for thriving not despite whatever happens but because of it?
  • Whatever obstacles stand in our way, we have a choice: be blocked or move through them.
  • Challenges help us build skills and resilience, called “adversarial growth.”
  • Facing obstacles, we experience similar feelings: fear, frustration, confusion, helplessness, depression, and anger.
  • Blaming others is easy, but the only thing we can control is our attitude.
  • “Great individuals, like great companies, find a way to transform weakness into strength.”
  • Common obstacles: mental, physical, emotional, and perceived.
  • “The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”
  • “The things which hurt, instruct.” - Benjamin Franklin
  • Framework for transforming obstacles into strengths: perception, action, and will.
  • Remaining resilient, adaptable, and calm when confronted with obstacles is learned behavior. Rockefeller called this “the school of adversity and stress.”
  • Perception of obstacles is more important than the obstacles themselves.
  • “Nothing either good or bad, but thinking makes it so.” - William Shakespeare
  • Events are objective until we assign meaning through story-making. 
  • Apatheia: Greek word for “calm equanimity.”
  • Learn to control your emotions, or as Nassim Taleb puts it, “domestication” of feelings.
  • “The observing eye sees simply what is there.”
  • When someone intimidates you, picture them having sex—grunting, groaning, and awkward in private—just like the rest of us.
  • Learning to perceive things as they are is a learned skill requiring repetition.
  • Breaking something apart causes it to lose its power over you.
  • Focus on that which is within your control, not what is not.
  • Animals don’t interpret and judge events; only humans do.
  • “Genius is the ability to put into effect what is in your mind. There’s no other definition of it.” - F. Scott Fitzgerald
  • Steve Jobs learned to reject first judgments because they’re inevitably fear-driven.
  • “There is good in everything, if only we look for it.” - Laura Ingalls Wilder
  • Socrates said his mean, nagging wife helped him practice philosophy.
  • “The extent of the struggle determines the extent of the growth.”
  • Action, the solution to our predicaments, must always serve the whole.
  • When facing an obstacle, do you fold or rise to the challenge?
  • We ignore and pretend, but deep down we know action is the only way out.
  • Courage, at its most basic level, is just taking action.
  • “Genius often really is just persistence in disguise…working at it works.”
  • Epictetus used to say: “Persist and resist.”
  • “It’s okay to be discouraged. It’s not okay to quit.”
  • As individuals, we are increasingly expected to be self-reliant, a start-up of one.
  • “Action and failure are two sides of the same coin.”
  • Failure shows us what isn’t the way.
  • Disorder and distraction are the enemies of action.
  • “When action is our priority, vanity falls away.”
  • Focus on results, not pretty methods.
  • “Think progress, not perfection.”
  • Søren Kierkegaard preferred implicity showing others new ways of seeing rather than explicitly saying “do this” or “think that.”
  • Ordinary people quit at failure; extraordinary people keep moving forward.
  • Will is more about surrender than strength.
  • “The path of least resistance is a terrible teacher.”
  • Plans rarely resemble reality.
  • Plan for failure but be ready for success.
  • Complaining is easy, but acceptance is the only answer to whatever is not within our control.
  • Situations can always be worse.
  • Doing great things requires enduring setbacks and tragedy.
  • Is it something you have to do or get to do?
  • There’s good and bad in everything.
  • Playing the long game allows you to persevere.
  • “Made weak by time and fate, but strong in will. To strive, to seek, to find, and not to yield.” - Tennyson
  • Death makes life purposeful and helps us prioritize.
  • Memento mori: remember you are mortal.
  • Awareness of death makes us less petty and more gracious and appreciative.
  • After we surmount one obstacle, another appears.
  • See clearly, act correctly, and surrender to the world as it is.
  • Action, not thought, is the essence of philosophy.
  • What philosophy should be: “an operating system for the difficulties and hardships of life.”

Related Resources

Here is a list of resources, including authors, books, websites, podcasts, and concepts mentioned in The Obstacle Is the Way, which might be helpful for further learning.


  • Ulysses S. Grant
  • Thomas Edison
  • Margaret Thatcher
  • Samuel Zemmurray
  • Amelia Earhart
  • Erwin Rommel
  • Dwight D. Eisenhower
  • Richard Wright
  • Jack Johnson
  • Theodore Roosevelt
  • Steve Jobs
  • James Stockdale
  • Laura Ingalls Wilder
  • Barack Obama
  • Nassim Taleb
  • Epictetus
  • Friedrich Nietzsche
  • Søren Kierkegaard
  • Gary Klein
  • Francis Bacon
  • Alfred Lord Tennyson
  • Thomas Gray
  • Marcus Aurelius
  • Cato
  • Seneca
  • Thomas Jefferson
  • Theodore Roosevelt
  • George Washington
  • Adam Smith
  • Joseph Brodsky
  • Ambrose Bierce
  • Mark Twain
  • H. L. Mencken
  • Beatrice Webb

Books and Publications

  • The Book of Five Rings by Miyamoto Musashi
  • The Gift of Fear by David De Becker
  • On Liberty by John Stuart Mill
  • Meditations by Marcus Aurelius
  • Enchiridion by Epictetus
  • Letters of a Stoic by Seneca
  • Discourses by Epictetus
  • The Inner Citadel by Pierre Hadot
  • Philosophy as a Way of Life by Pierre Hadot
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