Philosophy & wisdom

The Obstacle Is the Way

Ryan Holiday

The Timeless Art of Turning Trials into Triumph: how the Stoic way of seeing, acting and enduring turns a problem into a path

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  • 14 key ideas
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  • Published 2014

Introduction

Ryan Holiday takes one line from the Roman emperor Marcus Aurelius, "What stands in the way becomes the way", and turns it into a practical method for dealing with problems. He draws on the Stoic philosophers, mainly Marcus Aurelius, Seneca and Epictetus, and on short stories from history, sport and business, from John D. Rockefeller and Ulysses S. Grant to Amelia Earhart, Thomas Edison and James Stockdale.

The book has three parts, one for each of three disciplines. Perception is about seeing a problem as it really is, without panic. Action is about attacking it with energy, persistence and creativity. Will is about enduring and accepting what cannot be changed. Each part is made of short chapters that open with a quotation, and the book ends with Marcus Aurelius again.

Notes: Holiday says himself that the book is not a history of Stoicism. Its stories are short retellings, and some details in them are simplified or disputed by historians; this summary retells them as Holiday does and leaves out details we could not confirm. His judgments of people and events are reported as his. This summary follows the first edition, of 2014. The Dari quotes are our own translation of Holiday's English.

  1. 1Holiday builds the book on one line of Marcus Aurelius, that what stands in the way becomes the way, and turns it into three disciplines: perception, action and will
  2. 2Holiday argues that no event is good or bad until we judge it, so the first thing in our control is how we see the obstacle
  3. 3Holiday says nerve and calm are skills that can be trained: before solving a problem, steady yourself and set aside emotions that change nothing
  4. 4Holiday shows how to see a problem objectively: separate what happened from the judgment added to it, and change the frame you put around it
  5. 5Holiday says to spend your effort only on what is up to you, and only on the moment in front of you
  6. 6Holiday argues that after calming down and seeing clearly, the next step is a deliberate flip: looking for the opportunity inside the obstacle
  7. 7Holiday says action is the answer: start now, push with energy, and keep attacking the problem from new sides until it gives way
  8. 8Holiday treats failure as a lesson and the process as the way through: do the next small step well, whatever the task
  9. 9Holiday argues for doing what works: be practical, come at the problem from the side, and when the obstacle is too strong, let it defeat itself
  10. 10Holiday says to turn limits into fuel and a crisis into a chance to move, while being ready for none of it to work
  11. 11Holiday calls the will the discipline of the heart: an inner strength built in good times and kept firm by expecting what could go wrong
  12. 12Holiday says to accept what you cannot change, and then go further and love it: amor fati, love of fate
  13. 13Holiday says a lasting will means persevering through obstacle after obstacle and serving something bigger than yourself
  14. 14Holiday closes with death, with obstacles that never end, and with Marcus Aurelius forgiving a rebel: see clearly, act rightly, endure

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The Obstacle Is the Way by Ryan Holiday: summary | Daridanesh