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The Obstacle is the Way

By Ryan Holiday

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About the book

Ryan Holiday takes his title and premise from a line in the Meditations of Marcus Aurelius about obstacles becoming the path forward, and argues that how people respond to adversity defines them. Drawing on Stoic philosophy, he arranges the book around three disciplines: perception, action and will. Each part leans on historical figures, among them John D. Rockefeller, who kept his head through market turmoil, as well as Steve Jobs, Ulysses S. Grant and Amelia Earhart. The perception section covers staying objective, keeping poise under stress and separating what is in one's control from what is not. It was his third book. Holiday left college at nineteen to apprentice with the author Robert Greene.

Matthew McConaughey pointed to it when talking about the need for resistance and for picking the harder challenge for the right reasons, and Joe Rogan praised how well Holiday gathered its ideas and said he expects to return to it often. Steven Pressfield endorsed it.

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This book has 19 recommendations

Steven Pressfield (Author/The War of Art)

Follow these precepts and you will revolutionise your life.

Jimmy Soni (Managing Editor/Huffington Post)

An absolute must-read... Learn to tear through any obstacle and resolve any conflict.

Chris Guillebeau (Author/The $100 Startup)

First came Marcus Aurelius, then Frederick the Great... and now there's you. This surprising book shows you how to craft a life of wonder by embracing obstacles and challenge.

Nancy F. Koehn (Historian and leadership expert/Harvard Business School)

In this tight, engaging book, Ryan Holiday shines a bright, powerful light on the path to living and leading well. By showing us how to turn failure, obstacles and plain old every-day frustration to our advantage, he offers up a host of easy-to-use tactics that each of us can put to work to follow our dreams. Read it, learn from it, and get cracking!

James Altucher (Author/Choose Yourself)

My life has been beset with obstacles. It takes practice (and pain) to surmount them and achieve success. Ryan's book is a how-to guide for just that.

Recommended by Marvin Liao (Partner/500 Startups)

Source: Book-Talk with Marvin Liao, Partner at 500 Startups, Avid Reader & Tsundoku

Recommended by AnneMarie Schindler (Founder/Small Wins Consulting)

Source: AnneMarie Schindler, Founder of Small Wins Consulting, and the Books that Shaped Her Core Values

Chris Oliver (Founder/GoRails)

I remember reading The Obstacle Is The Way by Ryan Holiday on a road trip one time. It was during a time that I was feeling particularly frustrated with my business and was just having an all around hard time. The idea of the book is that if you recognize things are hard, you should keep going. It teaches you to seek out the obstacles because few people even try and even fewer make it past the obstacles. When I got home from my trip, I remember sitting down and realizing I was being stubborn and not doing the work I needed to do. Immediately, I could tell things were heading in a much better direction.

Marin Gerov (Co-Founder/DULO)

The Obstacle is the Way is another one of his creations that is more related to Stoic philosophy.

Cliff Hartono (CEO/Jasri Partners)

One of my favourite business books is probably The Obstacle is the Way by Ryan Holiday. Taking inspiration from Marcus Aurelius, Seneca and other historical figures, he successfully gives the reader actionable steps that apply Stoicism in a modern context.

Garrett Moon (CEO & Co-Founder/CoSchedule)

Ryan Holiday’s book, The Obstacle is the Way is a great read for any entrepreneur feeling frustrated with time and process. The reality is that the hardship and roadblocks that take 10 years to get through are the payment for success. You have to learn to embrace the process, not the outcome.

David McCammon (Photographer)

This book is great for anyone who cares to take a good look in the mirror and own your stuff. Early on Ryan states, “The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.” Holiday consistency challenges the reader to look at problems from a different perspective. A great read for entrepreneurs and those in pursuit of personal growth alike.

Cody McLain (CEO/SupportNinja)

This book introduced me to the concept of Stoicism and how we can choose to be happy instead of always vying for something in the future. This book teaches one that when faced with a challenge or obstacle, one should continue to pursue the goal as that is the way towards success, happiness and fulfillment.

Anant Jain (Co-Founder/CommonLounge)

It’s an excellent, modern-day recap of the Stoicism Philosophy, and I highly recommend it.

Chris Goward (Founder/WiderFunnel & GO Group Digital)

Here are some of the books that have been very impactful for me, or taught me a new way of thinking: [...] The Obstacle is the Way.

Jeremy Boudinet (Marketing Manager/Nextiva)

The Obstacle is the Way is another great book that challenges conventional wisdom and outlines the virtues of stoicism in the face of adversity and how to apply stoic principles in your own life.

Joe Rogan (Podcaster/Joe Rogan Experience)

@ryanholiday did a great job of compiling some very powerful and interesting thoughts in his book, “The Obstacle Is The Way.” I feel like it’s one I’m going to go over often. There’s some great stuff in here.

Alex Hormozi

On Alex Hormozi’s Business Books Tier List (Alex Hormozi, YouTube)

Matthew McConaughey

I will say this, as with the book The Obstacle Is The Way, and I've touched on this in my book a lot in my own way, look, the need for resistance, the need to choose the right, harder challenge. The need to choose a harder decision for the right reasons.

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See more books recommended by

Steven Pressfield, Jimmy Soni, Chris Guillebeau, Nancy F. Koehn, James Altucher, Marvin Liao, AnneMarie Schindler, Chris Oliver, Marin Gerov, Cliff Hartono, Garrett Moon, David McCammon, Cody McLain, Anant Jain, Chris Goward, Jeremy Boudinet, Joe Rogan, Alex Hormozi, Matthew McConaughey

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