Book Review: The Obstacle is the Way by Ryan Holiday

by Matt Jones, CPA

This book tends to find you when you need it. Maybe it’s finding you now too.

The meaning of the title is: a change of perspective; from this obstacle is in my way, to pushing through this obstacle will teach me the skills and give me the experience to succeed in the long run.

I bought it for the first time in January 2016 (after hearing Ryan Holiday on the Tim Ferriss Podcast) and I couldn’t put it down. I quickly read it twice and have picked it up many times  since. The wisdom and outlook of this book has helped me navigate good times (marriage, career change) and challenging times (rental property management and breaking my shoulder) – reminding me to remain calm as medical bills started pouring in, and be patient while working up to and through physical therapy. It also served as the inspiration for me to turn my weeks immobilized on the couch into the opportunity to build a website, share my thoughts, explore social marketing strategies, and begin to build a brand.

The Obstacle is the Way is extremely popular among NFL coaches, business leaders and innovators. It’s no surprise, given Holiday’s explanation of the book’s premise:

“Stoicism as a philosophy is really about the mental game. It’s not a set of ethics or principles. It’s a collection of spiritual exercises designed to help people through the difficulty of life. To focus on managing emotion; specifically, non-helpful emotion.”

Don’t get hung up on the fact the book is an introduction to Stoicism. Holiday does a fantastic job of providing both present day and historical examples to pierce the myth that our idols are without struggle or setbacks. It is struggle and setback that form the character which propels “champions” to the top of their field.

It’s no coincidence that The Obstacle is the Way has finally made it to the top of best seller lists (since being released in 2014) just as the world faces a global crisis in the form of the COVID-19 pandemic. I’ve leveraged the lessons of this short read to face my own life challenges and thought it was the perfect book to recommend to everyone at this time. It’s one of my favorite books to recommend and give as a gift. On top of that, as of this writing it is available instantly on kindle for only $1.99.

Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.

Andy Grove, former CEO of Intel

Many of my readers are from Cleveland, Ohio. No surprise, as Cleveland is my hometown. I’ve found it surprising that not all Clevelanders know that John D. Rockefeller got his start in Cleveland (despite a prominent downtown building bearing his name). Holiday opens this book with the story of Rockefeller (on page 13) earning 50 cents a day before the Panic of 1857.1

Oh, how blessed young men are who have to struggle for a foundation and beginning in life. I shall never cease to be grateful for the… difficulties to be overcome, all along the way.

John D. Rockefeller

I can’t help but notice parallels, that one of the most successful investors of all time got his start during a depression.2For all those college seniors facing a suddenly uncertain job market and for those seasoned professionals who find themselves nervous about the future, I hope this book provides reassurance while we manage our current situation: a global virus wreaking havoc on our most vulnerable while shutting down social and business activity.

What if? What if you could steady your nerves and grow during this time rather than just hope to maintain?

Many people experienced the same perilous times as Rockefeller – they all attended the same school of bad times. But few reacted as he did. Not many had trained themselves to see opportunity inside this obstacle, that what befell them was not unsalvageable misfortune but the gift of education–a chance to learn from a rare moment in economic history.

Ryan Holiday

These aren’t entirely new ideas. In fact, these ideas are millenia old, guiding principles of everyone from the American Presidents (like James Garfield, another Clevelander) to Alexander the Great. 

The impediment to action advances action. What stands in the way becomes the way.

Marcellus Aurelius

This book is the summation of thousands of years of lessons and logic boiled down into a quick, easy read. Short chapters partnered with historical quotes, stories and lessons make it a quick read. This isn’t to negate the importance of the larger works, letters, philosophies, and stories behind these greeting-card-length mantras, and if you have the time, I would encourage you to dive into the original writings Chapters are only five to ten pages long and full of stories of leaders turning their greatest challenges into learning lessons which guide them to success. I like to read a chapter, put the book down and reflect on it while relaxing, exercising or cleaning. 

Things which hurt, instruct.

Benjamin Franklin

A great number of us are experiencing the same stress and challenges today. We have little input over how our governments react and how this virus spreads. However, what we do have control over is our attitude and actions. Some of us will grow during this time, learning new skills, reconnecting with family/friends, and planning for once things go back to (the new) normal. Your attitude and reaction are entirely under your control. 

Nothing is either good or bad, but thinking makes it so


Also read: The 48 Laws of Power by Robert Greene, Ryan Holiday’s mentor.


CJ Nusbaum March 22, 2020 - 3:51 pm

Thanks for sharing, Matt! This one is on my Goodreads list…perhaps this is the perfect time to start it. Take care!

Matt Jones, CPA March 22, 2020 - 3:56 pm

I think you’re right, CJ, perfect time. Hope you enjoy it let me know!

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