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The Obstacle Is the Way

The Timeless Art of Turning Trials into Triumph

This book can be downloaded and read in iBooks on your Mac or iOS device.


The Obstacle is the Way has become a cult classic, beloved by men and women around the world who apply its wisdom to become more successful at whatever they do.

Its many fans include a former governor and movie star (Arnold Schwarzenegger), a hip hop icon (LL Cool J), an Irish tennis pro (James McGee), an NBC sportscaster (Michele Tafoya), and the coaches and players of winning teams like the New England Patriots, Seattle Seahawks, Chicago Cubs, and University of Texas men’s basketball team.

The book 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.” 

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.

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.

From the Hardcover edition.

From Publishers Weekly

Mar 10, 2014 – Holiday (Trust Me, I'm Lying), "media manipulator" and master of the dark art of marketing, returns with a collection of bite-sized, intensely written aphorisms and parables about learning how to see "through the negative, past its underside, and into its corollary: the positive." Starting with figures no less august than Marcus Aurelius and John D. Rockefeller, Holiday collects historical anecdotes from politics, commerce, sports, and history as well as some light re-readings of classical philosophy and loosely structures them around the three skills he sees as essential to succeeding in the face of adversity: perception, action, and will. These sections outline stories and limited strategies that will encourage readers to creatively redefine obstacles as opportunities, act with less fear of failure by better processing the emotion, and develop the "resilience" and "flexibility" necessary to soldier through difficult situations. Holiday's charismatic, if slightly Delphic, stories will be welcomed by readers of The 48 Laws of Power and similar works of advice, but frustrating to readers accustomed to more empirically sourced and pedagogically developed works on motivation and adversity. Still, Holiday's performance is commanding and optimistic, sure to inspire readers to take new perspective on their apparent obstacles.

Customer Reviews

An awesomely inspiring read!

I’ve read Ryan Holiday’s previous two books, but this is by far his best work yet. Cheers to Holiday for celebrating the art of failing well rather than casting failure as a necessarily negative life event. We’re all bound to face difficulties, so why not choose to learn from them rather than throw our hands up in the air? Holiday illustrates the stoic way of life by drawing upon a wide array of specific examples involving many of the great leaders, inventors, and thinkers who have embraced stoicism over the centuries. The anecdotes he focuses on are enjoyable to read as tasty nuggets of history. More importantly, each story is relatable, and human. The structure of the book, which is divided into three parts, reflects the threefold philosophy he advocates. I cannot recommend this book highly enough! If you’re anything like me, after finishing, you won’t be able to stop saying: “The obstacle is the way!"

Inspirational Read

More than any other book in recent memory, this book moves me to read more about the subject. Very helpful and encouraging content. Organized to be used as a great resource for furthering knowledge and improving your life.

I love this perspective! Page turner!

This book is so amazing! I love the perspective and the use of history to back up the philosophy. It's really changing the way I view things. I just want to kiss the author!

The Obstacle Is the Way
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  • $9.99
  • Available on iPhone, iPad, iPod touch, and Mac.
  • Category: Management & Leadership
  • Published: May 01, 2014
  • Publisher: Penguin Publishing Group
  • Print Length: 224 Pages
  • Language: English
  • Requirements: To view this book, you must have an iOS device with iBooks 1.5 or later and iOS 4.3.3 or later, or a Mac with iBooks 1.0 or later and OS X 10.9 or later.

Customer Ratings