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.
We hope you love the books people recommend! Just so you know, The CEO Library may collect a share of sales or other compensation from the links on this page.
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.
On Alex Hormozi’s Business Books Tier List (Alex Hormozi, YouTube)
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.
This book is part of our collection:
Get this book on Amazon | Barnes & Noble | Apple Books
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
See more books written by
Often recommended alongside
- The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss (5 shared recommenders)
- The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz (4 shared recommenders)
- Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb (4 shared recommenders)
- How to Win Friends and Influence People by Dale Carnegie (3 shared recommenders)
- Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel and Blake Masters (3 shared recommenders)
- Man’s Search for Meaning – The Classic Tribute to Hope from the Holocaust by Viktor E. Frankl (3 shared recommenders)
Appears in collections
- Best Books About Resilience and Building Mental Strength
- Best books on stoicism: modern & classic stoic books
- Best Non-Fiction Books of 2019 – 80 books recommended by The CEO Library community
- Best Startup Books – More than 150 books to read
- Best Stock Market Books for Every Level
- Best Inspirational Books: For When You Need to Get Inspired
- Best Books for Managers: You Need to Manage People If You Start Your Company
Sources
- The Obstacle is the Way [book blurb]
- Book-Talk with Marvin Liao, Partner at 500 Startups, Avid Reader & Tsundoku
- AnneMarie Schindler, Founder of Small Wins Consulting, and the Books that Shaped Her Core Values
- Chris Oliver, Founder of GoRails, Gives Enthusiastic Insight on The Books that Helped Him Grow
- Marin Gerov, Co-Founder of DULO, Learned at Least One Valuable Lesson from Each Book Read
- Cliff Hartono, CEO of Jasri Partners, Believes You Need to Find Authors to Relate to
- Garrett Moon, CEO & Co-Founder of CoSchedule: ''Books will trigger moments of clarity for me as a leader''
- Photographer David McCammon Shares an Insightful List of Reads for Every Picture Lover
- Cody McLain, CEO of SupportNinja, Shares the Books that Provide the Right Business Framework
- Book-Talk with Anant Jain, Co-Founder of CommonLounge: Common Entrepreneurial Mistakes & Reading Habits
- Chris Goward, Author & Founder of Conversion Optimization Company WiderFunnel, on the Books That Taught Him a New Way of Thinking
- Interview with Jeremy Boudinet, Marketing Manager at Nextiva: Favorite Books and Reading Habits
- Joe Rogan (@joerogan) Instagram post, 2022-05-16
- Business Books Tier List (Alex Hormozi, YouTube)
- The Tim Ferriss Show Transcripts: Matthew McConaughey — The Power of "No, Thank You," Key Life Lessons, 30+ Years of Diary Notes, and The Art of Catching Greenlights (#474)


