The Obstacle Is the Way
Insightful
Predictable
Dry

The Obstacle Is the Way The Timeless Art of Turning Trials into Triumph

Ryan Holiday2014
#1 Wall Street Journal Bestseller 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.
Sign up to use

Reviews

Photo of Christian Bager Bach Houmann
Christian Bager Bach Houmann@cbbh
5 stars
Jul 20, 2024

A must read. I highly recommend this book.

Photo of Haikal Satria
Haikal Satria@haikalstr
5 stars
Apr 4, 2024

Lighter reading than Marcus Aurelius's Meditations, The Obstacle Is The Way is a very accessible pathway to the school of Stoicism. Using a combination of amusing anecdotes and understandable vernacular, Holiday makes a thousand year old concept interesting for the masses, and I am very thankful to him for that. My favorite passage is in a chapter about preparing for intervention and disruption, in which Holiday says that we must always prepare ourselves by asking ourself 'What if?' But sometimes, the answer to 'What if?' is simply: It will suck, but we'll be okay.

Photo of Anton
Anton@tonyv
2 stars
Feb 12, 2024

This books is a good introduction into stoicism as well as a brief collection of stories about modern day stoics. I give it too stars just because I feel like it’s overrated here. There are much better stoic books on Goodreads with rating below this one. Little Book of Stoicism, for example. Or, as the author suggested, read the originals that also have worse reviews.

Photo of Akeisha
Akeisha@akeishaiskandar
3 stars
Nov 18, 2023

Interesting!

+3
Photo of Jacob Medure
Jacob Medure@jacobs_blue
4 stars
Jun 16, 2023

Breakthrough capable book. Essential and timeless messages made accessible to the modern layman (me) haha. Just really good advice.

Important read imo.

Photo of Dylan Stewart
Dylan Stewart @vdowiz
2.5 stars
Mar 25, 2023

An OK book, but certainly not anything new or life altering. It was obvious that the author was a student of Robert Greene (whose books I LOVE), because it followed a similar format of telling a lesson, then sharing a historical example that underscores the lessons, but it was unmemorable.

+3
Photo of Charlotte Dann
Charlotte Dann@chareads
4 stars
Feb 6, 2023

Update March 2018: I've really loved re-listening to this book, it's made me realise how far I've come since I first read it in terms of choosing to approaching problems stoically. Six months ago I cried a lot from putting myself in risky/stressful situations and felt very helpless, and now I'm still doing those things (lol), but my response to them is unceasing positivity and confidence. I'm actually living the wisdom of this book! It'll be interesting to come back to it in a year or so and check in on my progress. Original review (October 2017): a) This is really good and if you keep the sentiment present in your mind whenever you face adversity it will be immensely helpful. b) it's just a collection of aphorisms, bastardised stoicism, and 'YOU CAN DO IT' cheer.

Photo of Julien Sobczak
Julien Sobczak@julien-sobczak
4 stars
Oct 22, 2022

Start seeing obstacles as not so bad, but simply as good. A good book, the first one in the author’s trilogy, but probably the less mind opening. I doubt many readers will be surprised by the importance of obstacles on the road to success. What I found interesting, however, is the use of ancient philosophy, mainly Stoicism, to illustrate how persistence and ingenuity has always being keys to overcoming any obstacle – mental, physical, emotional. As outlined by the author, this book is not a replacement for classic books on Stoicism, often quoted by the author. But you don’t need to read these books first, even if like me, I bet you will add more than one title on your reading list. You will hear a lot about Seneca, Epictetus, Marcus Aurelius, key figures in ancient Rome, but also about people closer to us. Ryan Holiday did a lot of research in books, especially biographies, to share collective wisdom illustrated with true stories, a perfect mix between pragmatism and history. I strongly recommend the whole trilogy, not just this book. There are many powerful insights in Stoicism, and Ryan Holiday is the best author to present old recipes from antics in a modern and engaged way.

Photo of Benjamin Harrison
Benjamin Harrison@c0nsilience
5 stars
Aug 12, 2022

This is the second time I've read this book and it was my introduction to Stoicism several years ago. The title is taken from Marcus Aurelius' Meditations and Ryan Holiday does a good job of modernization a lot of these principles.

+3
Photo of Cams Campbell
Cams Campbell@cams
2 stars
Jul 31, 2022

I was so excited to read this after going through Ryan's 7-day email sequence. I got as far as P75 before I couldn't read any more. It reads like it's written for high school kids, which is fine. I'm just not one of them. I think I'll head straight to Aurealias' Meditations and learn about stoicism that way.

Photo of Emily Medic
Emily Medic@emilymedic
4 stars
Feb 24, 2022

I read it for the focus on stoicism, but was pleasantly surprised about all the real-time examples. Jumping through history was quite enjoyable, and I’d definitely re-read it.

+4
Photo of Ivaylo Durmonski
Ivaylo Durmonski@durmonski
5 stars
Oct 29, 2021

Probably you won’t find anything new in this book in terms of handling obstacles – spot the opportunity in every tough situation, break the challenge into pieces to handle it, etc. However, you’ll get something much more valuable – motivation. The stories shared inside The Obstacles is The Way, and how key players in our history coped with adversity, will help you find solutions in your daily life. The way Ryan Holiday structured this book is exceptionally good. Instead of long chapters with a never-ending resolution, you get short sections each covering one story and each offering one specific lesson. If you’re trying to run a business in tough conditions or you’re baffled every time a challenge arises, you should definitely consider this book. Key takeaway? Obstacles never cease to exist. Deflecting them or trying to hide from them will only cause you harm. When times are good, improve yourself. This way you’ll be better prepared when bad things actually start to take place. Read full summary: https://durmonski.com/book-summaries/...

Photo of Christina Wells
Christina Wells@christinaw
2 stars
Oct 4, 2021

If you want to read a really long and trite motivational poster, then this book is for you.

Photo of Lucas Coelho
Lucas Coelho@coelholucas
4 stars
Sep 20, 2021

This book did nothing to me. But it was me, not the book I feel. Having read Meditations many times and Seneca's Letters and other stoicism books I believe it is so much you can gather from this simple life philosophy by just reading it, especially when the book is so superficial or 'entry-level' like The Obstacle is the Way. Also, the anecdotes feel more like survivorship bias to me than actually adding to the philosophy. I can see what Ryan was aiming here and the public so I am still giving 3 stars as the read in itself was not unpleasant, but if you are already into stoicism you can easily skip this book.

Photo of Randy Robbins
Randy Robbins@rjrobbins2
5 stars
Sep 14, 2021

This book is one of those that you read one chapter a day and take wisdom you can apply immediately. I got this at the library but I will be purchasing a copy to keep on my main bookshelf and revisit often. If I had pursued a dream of teaching high school, I would require this book as reading. Everyone in the world can find value in this book.

Photo of Luca Conti
Luca Conti@lucaconti
2 stars
Sep 10, 2021

disappointing

Photo of Yasmin S.
Yasmin S.@warmcupofmagic
5 stars
Aug 30, 2021

One of my current favorite books ever.

Photo of Adam
Adam@adam
5 stars
Aug 17, 2021

When reading about modern stoicism, this one kept coming up as a book recommendation. The focus is on resiliency and growth mindset when it comes to opposition. This may seem like common advice, but it's sometimes most difficult to remember when in the worst positions.

Photo of Eihab Khan
Eihab Khan@eihab
4 stars
Aug 12, 2021

One of my all-time-favorite books

Photo of Clint Bedwell
Clint Bedwell@clintbedwell
5 stars
Jan 5, 2025
+3
Photo of Fortune Atuakpoho
Fortune Atuakpoho@oldmateforty
3 stars
Oct 2, 2023
+1
Photo of Radimir Bitsov
Radimir Bitsov@radibit
4.5 stars
Jul 11, 2023
+2
Photo of Natalie Unsinn
Natalie Unsinn @natalieunsinn
3 stars
May 6, 2023
Photo of Eneko Uruñuela
Eneko Uruñuela@eurunuela
4 stars
Mar 14, 2023
+2

Highlights

Photo of Rina
Rina@rinareads

Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible.

Page 101
Photo of Rina
Rina@rinareads

Finishing the smallest task you have right in front of you and finishing it well.

Page 88
Photo of Rina
Rina@rinareads

The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this.

Page 57
Photo of Rina
Rina@rinareads

Our best ideas come from there, where obstacles illuminate new options.

Page 52
Photo of Rina
Rina@rinareads

Would you have a great empire? Rule over yourself.

Page 27