The Obstacle Is the Way – Bookcast #28

The Obstacle Is the Way (2014) by Ryan Holiday

Ryan Holiday’s modern classic The Obstacle Is the Way draws its inspiration from stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. 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, tougher. As Marcus Aurelius put it nearly 2000 years ago: “The impediment to action advances action. What stands in the way becomes the way.” 

This book demonstrates how some of the most successful people in history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—have applied stoicism to overcome difficult or even impossible situations. Their choice to embrace these principles ultimately mattered more than their natural intelligence, talents, or luck.

If you’re feeling frustrated, demoralized, or stuck in a rut, this book can help you turn your problems into your biggest advantages. And along the way it will inspire you with dozens of true stories of the greats from every age and era.

Read and listen to “The Obstacle Is the Way on Amazon!


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  • A very brief description of “The Obstacle Is the Way”
    • Ryan Holiday shows us how some of the most successful people in history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—have applied stoicism to overcome difficult or even impossible situations. Their embrace of these principles ultimately mattered more than their natural intelligence, talents, or luck.
  • What Holiday sets out to do / Purpose of the book
    • To introduce stoic philosophy to the modern reader and show how amazing stoicism is – and how damn practical – it still is over 2,000 years later
  • What challenges/problems does it attempt to solve?
    • To give the reader tools to transform our greatest challenges into our greatest successes
  • The intended audience of the book / Who will benefit most?
    • Anyone who loves philosophy
    • Anyone who believes in self-improvement
    • Anyone who enjoys real-life examples of famous people succeeding through hard times
    • Anyone who wants an optimistic – and practical – application of psychology
    • Greek-o-philes
  • Who probably WON’T like “The Obstacle Is the Way”?
    • Someone who doesn’t like challenge or discomfort
    • People who own rose colored glasses (and won’t take them off)
    • Idiots
  • How does this book specifically benefit Men? 
    • Blueprint of great men from history – shows us what we should do, how we should act
  • Is this book Easy, Average or Difficult to read? / How long is it?
    • Easy to read, almost bite sized pieces with a story and a lesson
    • Print: 224 pages – About 4-5 hours
    • Audio: 6 hours 7 min
    • What are the overall book reviews?
  • Short bio of Ryan Holiday
    • Ryan Holiday (born June 16, 1987) 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.
    • Holiday began his professional career after dropping out of college at the age of 19. He attended University of California, Riverside, where he studied political science and creative writing.
    • He worked with Robert Greene on Greene’s 2009 New York Times bestselling book, The 50th Law.
    • Holiday has written for Forbes, Fast Company, The Huffington Post, The Columbia Journalism Review, The Guardian, Thought Catalog, Medium.com, New York Observer and the New York Times 
    • Has written multiple best-selling books including:
      • Trust Me, I’m Lying: Confessions of a Media Manipulator
      • The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
      • Ego Is the Enemy
      • The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living
  • Table of Contents / Breakdown of Themes
    • 3 major sections
      • Perception
      • Perspective
      • Will
    • We should face our obstacles with the following:
      • Energy
      • Persistence
      • Deliberate processes
      • Resilience
      • Pragmatism
      • Strategic vision
      • An eye for opportunity
      • Craftiness
    • The Stoic grows stronger and better with every obstacle they face. They rally to every challenge and thrive as a result. So can you.


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