Book Brief: The Obstacle Is the Way

The Timeless Art of Turning Trials into Triumph

Author

Scott D Johnson
May 08, 2024

This week’s issue is a Book Brief where I provide a glimpse into one of my favorite books and summarize the key strategies hidden within it.

The Obstacle Is the Way by Ryan Holiday

Drawing inspiration from the ancient Stoics, Holiday serves up a series of lively anecdotes and insights that turn conventional wisdom on its head. Instead of dodging life's obstacles, we learn to embrace them.

Packed with stories about historical figures who turned adversity into triumph, this book is a great companion as you face life's challenges.

A Glimpse Into the Book

The book highlights many stories to illustrate how historical figures used Stoic principles to navigate life’s challenges.

Here’s an excerpt about John F. Kennedy:

"In October 1962, the Cuban Missile Crisis put the world on the brink of nuclear disaster. The crisis began when American surveillance planes discovered Soviet missiles capable of carrying nuclear warheads being installed in Cuba, just 90 miles off the coast of Florida. This provocative act could have led to a catastrophic nuclear exchange between the United States and the Soviet Union.

President John F. Kennedy, understanding the gravity of the situation and the potential for massive destruction, chose a course of action that emphasized restraint over retaliation, calm over chaos. Instead of launching a direct military assault on Cuba, which many of his advisors and military officials were urging, Kennedy decided on a naval blockade. This blockade prevented any further missiles from being delivered to Cuba and signaled to the Soviet Union the seriousness of the U.S. stance, all without crossing the threshold into war.

Over the following tense 13 days, the world watched as these two nuclear superpowers stood at the brink. Kennedy engaged in intense negotiations with Soviet Premier Nikita Khrushchev, all while maintaining a public composure that reassured the American people and prevented panic. His leadership during these negotiations demonstrated a key Stoic principle: the importance of maintaining one's composure and not being swayed by external pressures or immediate emotional reactions.

Finally, a secret agreement was reached, where the U.S. promised to remove its missiles from Turkey in exchange for the Soviets dismantling their missile bases in Cuba. This resolution showcased Kennedy’s ability to leverage a dire obstacle into a strategic victory, ensuring peace and demonstrating that obstacles, no matter how insurmountable they seem, can indeed become the way forward if approached with wisdom and courage."

Ryan Holiday, The Obstacle Is the Way

In addition to JFK, here are some other personalities featured in the book:

  • George Clooney - Renowned actor and director who faced numerous rejections early in his career but used each setback as a stepping stone to further his ambitions.

  • James Stockdale - United States Navy vice admiral and aviator awarded the Medal of Honor in the Vietnam War, who used Stoicism to survive being a prisoner of war.

  • Eleanor Roosevelt - Former First Lady of the United States and a human rights advocate, who used her platform to address issues of racial injustice and the rights of women and workers despite facing personal and public challenges.

  • Thomas Edison - Inventor whose response to the fire that destroyed his lab exemplifies the Stoic response to setbacks.

  • Demosthenes - Ancient Greek statesman and orator, who overcame a speech impediment through persistent practice and determination to become one of Athens' greatest orators.

… and many others such as Julia Child, Amelia Earhart, Steve Jobs, Abraham Lincoln, John D. Rockefeller, Dwight D. Eisenhower, Ulysses S. Grant, Theodore Roosevelt, Winston Churchill, Erwin Rommel, Margaret Thatcher, Benjamin Franklin, Albert Einstein, Arthur Ashe, Jackie Robinson, Florence Nightingale, Samuel Zemurray, Malala Yousafzai, Josephine Bakhita, Marcus Aurelius and more.

(A Sidenote on Shortform)

I read the book several years ago, but this week I wanted to refresh my memory on the details so I downloaded Shortform to try it.

Shortform is more expensive than its competitors (Blinkist and Headway), but it is definitely the most robust summary app I’ve used. I also like how it references other books and provides counterarguments to provide a more well rounded understanding of the content.

Overall, I was really impressed with Shortform, and I thought it was worth the premium. But I still feel like it’s worth reading the entire book to pick up on the stories that bring the concepts to life.

If you decide to try Shortform, search for a discount code, and I believe you can get 14 days free this month.

Key Strategies in the Book

Here are the key points from the book that the Shortform summary expands on in more detail:

Part 1: Philosophy | Adopt an Empowering Worldview 

  • Truth #1: No Event Is Necessarily Good or Bad

  • Truth #2: You Can Choose To See Every Problem as an Opportunity

  • Truth #3: The Purpose of Life Is to Act on Opportunities

  • Exercise: Look for Hidden Opportunities

Part 2: The Internal Fight | Master Your Emotions

  • Strategy #1: Use Logic to Defuse Your Unhelpful Emotions

  • Strategy #2: Redirect Your Emotions Into Helpful Contexts

  • Strategy #3: Prepare for Long-Term Hardship

  • Strategy #4: Take Things Step-by-Step

  • Strategy #5: Motivate Yourself by Helping Others

  • Strategy #6: Accept Things for What They Are

  • Exercise: Practice Acceptance

Part 3: The External Fight | Do What It Takes to Succeed

  • Strategy #1: Act, Don’t Think

  • Strategy #2: Learn Something From Every Failure

  • Strategy #3: Set Unreasonable Goals

  • Strategy #4: Predict What Will Go Wrong

  • Strategy #5: Embrace Unconventional Paths to Success

  • Exercise: Be a Practical Pessimist

  • Exercise: Conquer Stubborn Obstacles

Each of these strategies may seem trite at surface level, but I’ve found it helpful to take the time to deeply reflect on each one.

Understanding the concepts is one thing… but remember that the real value comes from putting them into action (which is easier said than done).

I guess that’s why it’s an ongoing “practice.”

Don’t Take My Word For It

Check out this short clip where comedian Jerry Seinfeld talks about the impact Stoicism has had on his life.

Want to Learn More?

Read the book! Click here to buy The Obstacle Is the Way by Ryan Holiday.

Thanks for reading!

Until next week, keep growing »

Scott​

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