The Obstacle is The Way

The Obstacle is The Way

By Ryan Holiday

Click Here to Buy The Book From Amazon.

About the Author:

Ryan Holiday is a strategist and writer. He dropped out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written several other books that focus on both marketing & philosophy.


Why I read The Obstacle is the Way:

On the surface, the idea of me reading a book on philosophy is hilarious. I nearly failed the only philosophy course I took in college. So why read this book that focuses so much on the Roman philosophy of stoicism? Simple, I saw that many of the smartest leaders in the sports world were all reading it & having their organizations read it. I figured, if it’s good enough for them, it’s good enough for me.

Who were some of those people? Joe Maddon, Pete Carroll, Bill Belichick and Shaka Smart just to name a few. Like I said… good enough for them, good enough for me.

But why did they read it?

If you’re an athlete, a prospect, a recruit, a coach, a teacher, an employee, a business owner, a human of any kind, you are going to run across obstacles. Or at least things that you think are obstacles. How people handle those obstacles is what separates the good from the great. I want to be great.

My Review:

The format of this book goes a long way to ensuring that the message is digested.

Holiday hammers home the point that the obstacles we encounter in our lives are not the end of the world.

The book is broken into 3 main parts…

  • “Perception”… how we perceive an obstacle.
  • “Action”… how we act towards an obstacle.
  • “Will”… our internal power that keeps us moving forward.

The brilliance of the book is that each main part is broken into many small parts. Each small part is led with an example from a recognizable world leader. Each example teaches a small lesson.

Leaders mentioned in the examples include Thomas Jefferson, George Washington, Ulysses S. Grant, Thomas Edison, Margaret Thatcher, Amelia Earhart, Dwight D. Eisenhower, Steve Jobs, John D. Rockefeller, Warren Buffet, Rubin “Hurricane” Carter, Tommy John and on and on and on.

This book does not waste an opportunity to reinforce that “the obstacle is the way”. Meaning that the thing that is in your way right now will be the very thing that gets you to where you are going. Using that which is in our way is the key.  He describes this very well… “It’s simple. Simple but, of course, not easy.”

The key take away is that “obstacles are not only to be expected but embraced.” If we embrace the fact that every person encounters obstacles and we know we will too, then they will not shock us when they come & they will not ruin us when they come. Acknowledging this fact will help us adjust how we look at these obstacles… how we “perceive” them.

Adjusting how we perceive each obstacle that we encounter will prepare us for how we “act” towards each obstacle.

Action… putting 1 foot in front of the other… “is the solution and the cure to our predicaments.” But be cautious not to fall for the trap of action for the sake of action. Action must have “direction”.

As I read this book I thought a lot about the obstacles a prospect might encounter… be it learning to master a skill or perhaps navigating through the recruiting process. The following quote seemed like the solution for either…

“Therefore, we can always (and only) greet our obstacles

  • with energy
  • with persistance
  • with a coherent and deliberate process
  • with iteration and  resilience
  • with pragmatism
  • with strategic vision
  • with craftiness and savvy
  • and an eye for opportunity and pivotal moments

Are you ready to get to work?”

The final section of the book focused on “Will”. Reading this section made me think a lot about the difference between achieving or not achieving success. What is the thing that propels 1 person but prevents another from reaching the pinnacle? I think, in many cases, it simply comes down to “will”. What is it? Holiday says “Will is our internal power, which can never be affected by the outside world.”

He continues on to discuss 2 similar but different words… persistence & perseverance. He states that “Persistence is an action. Perseverance is a matter of will. One is energy. The other is endurance.” I think about the most elite person at any craft. To get there and stay there, an endurance that is unmatched is required. Think about those MLB players for example. It wasn’t enough that they were great. They were great AND they outlasted their competition. There were others that had a similar skill set, but withered away at some point due to the exhaustive nature of the profession.

Lesson Learned:

Once you’ve read & digested this book “Now you are a philosopher and a person of action.”

Once you’ve read & digested this book you should have “the powers of perception, action, and the will.

With this triad, they

  • First, see clearly.
  • Next, act correctly.
  • Finally, endure and accept the world as it is.”

Favorite Quotes:

*quotes of Ryan Holiday unless otherwise indicated.

“Really only one thing is at fault: our attitude and approach.”

“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.” – Andy Grove, former CEO of Intel

“Great times are great softeners.”

“Abundance can be its own obstacle, as many people can attest.”

“Because obstacles are not only to be expected but embraced.”

“Our perception can be a source of strength or of great weakness.”

“Be fearful when others are greedy and greedy when others are fearful.” – Warren Buffet

“A mistake becomes training.”

“Uncertainty and fear are relieved by authority. Training is authority.”

“We choose how we’ll look at things.”

“Most people start from disadvantage (often with no idea they are doing so) and do just fine. It’s not unfair, it’s universal.”

“Problems are rarely as bad as we think — or rather, they are precisely as bad as we think.”

“Action is commonplace, right action is not.”

“If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.”

“In the chaos of sport, as in life, process provides us a way.”

“As they say in Brazilian jujitsu, it doesn’t matter how you get your opponents to the ground, after all, only that you take them down.”

“The way that works isn’t always the most impressive.”

“We are prepared for failure and ready for success.”

“Persist and persevere.”

“The diagnosis is terminal for all of us.”

“Passing  one obstacle simply says you’re worthy of more.”

“The obstacle becomes the way.”

Thoughts? Comments? Your favorite quotes? Please feel free to comment in the thread below or email me directly. If you email me your thoughts directly I may post them anonymously in order to add to the discussion.