5-Star Book Review Club Presents: The Obstacle Is the Way by Ryan Holiday

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The Obstacle Is the Way by Ryan Holiday

TOP 3 LEADER EXAMPLES IN THE OBSTACLE IS THE WAY

If you need to improve your self-talk or your approach toward adversity, The Obstacle Is the Way by Ryan Holiday is a must read. It’ll give you so many ways to look at life’s obstacles, you’ll become better at handling anything that comes your way. The book uses Stoicism as its foundation, but it doesn’t get too bogged down on the subject like a book solely focused on Stoicism would. Holiday’s streamlined approach will make the book a page-turner for everyone lucky enough to absorb this material.

The author uses many leaders, so I can’t get into all of them. Instead, I picked the top three leaders used as examples to give you a hint of how Ryan uses them to aid his message. Even though the book uses many great leaders as examples, I chose Marcus Aurelius for his ability to use objectivity to keep himself level headed in any situation, Amelia Earhart for focusing on the goal rather than the insulting way someone approached her with her first flying job, and Jack Johnson for using a smile to win the “Fight of the Century” in an arena filled with hate, because they encompass the soul of the author’s message to the reader; Stoicism can overcome any obstacle regardless of what it is.

Marcus Aurelius

The first part of the book covers perception, so, according to the author, the way to perceive your circumstances is crucial to overcoming everything, including your own emotions in any situation. This is basically the “crawl before you run” step. So, when I reached the chapter called “Practice Objectivity,” this is when it hit me; one of the most important parts of perception is to practice the ability to remain objective. Another clue to the importance of objectivity is the author’s usage of the main inspiration of this book, Marcus Aurelius, as an example. The other examples were great, but Marcus sticks out because he comes up many times while you’re reading, and because he’s the most famous Stoic leader, making it feel as if he’s omnipresent in the book. It’s interesting because the previous example uses Epictetus, but it seemed like the strategy he told his students is similar to the cliché: when you’re nervous in front of a crowd, picture everyone naked. 

The strategy to remain objective, according to Aurelius, was to “describe glamorous or expensive things without their euphemisms—roasted meat is a dead animal and vintage wine is old, fermented grapes. The aim was to see these things as they really are, without any ornamentation” (34). This advice could help everyone because everyone has been affected by euphemisms and their ability to create exaggerated importance out of the most mundane, like when people admire a wealthy influencer’s purchases, forgetting this is just a person buying what their privileges bring them, and you, as the outsider, don’t know how this wealthy influencer attained their wealth or privilege; since, in reality, it’s just a person living their life. And this is why a paragraph later, the author brings up the advice associated with his example, which primarily comes down to using the same strategy as when you give someone else advice because “objectivity means removing ‘you’—the subjective part—from the equation” (34).

Amelia Earhart 

The second part of the book is about taking action, so I found no better universal example in the chapter “Get Moving” than Amelia Earhart because her example is the epitome of taking that first step in your career without letting the insulting way it’s brought to you hold you back. Even though the details associated with her first pilot job were offensive, accepting it was the paramount step Amelia took toward becoming “the first woman to fly solo nonstop across the Atlantic… [becoming] one of the most famous and respected people in the world. But none of that would have happened had she turned up her nose at that offensive offer or sat around feeling sorry for herself. None of it could have happened if she’d stopped after that first accomplishment either. What mattered was that she took the opening and then pressed ahead” (72). Earhart’s actions prove the first step, no matter what it is, is the most crucial part to proceed on any path. On an individual level, “we know what our problems are. We may even know what to do about them. But we fear that taking action is too risky, that we don’t have the experience or that it’s not how we pictured it or because it’s too expensive, because it’s too soon, because we think something better might come along, because it might not work. And you know what happens as a result? Nothing. We do nothing” (72). Using Amelia as an example for taking action was a brilliant moment in this book since it shows you the strength it took for Earhart to become one of the most famous people ever. Just imagine if she hadn’t accepted the offer and stayed a social worker. 

Jack Johnson

The next example is from part three, which teaches you to use will to overcome obstacles by surrendering to them. In different ways, we’ve all reached the point of wanting to give up when things are getting difficult, and it’s will that separates us. There’s no superior example in this part than the one that comes up in the chapter “Love Everything That Happens: Amor Fati.” It’s at this point that the author uses Jack Johnson to show how loving your dire situation, approaching it with a smile rather than freaking out or getting angry, will lead you to triumph. When Mr. Johnson fought in the “Fight of the Century,” it was 1910 and Johnson was the first African American world heavyweight champion, so you can imagine the immense racism he had to endure. He was “genuinely hated by his opponent and the crowd, [but enjoyed] every minute of it. Smiling, joking, playing the whole fight. Why not? There’s no value in any other reaction. Should he hate them for hating him? Bitterness was their burden and Johnson refused to pick it up. Not that he simply took the abuse. Instead, Johnson designed his fight plan around it… And when one well-placed blow opened a cut on Johnson’s lip, he kept smiling—a gory, bloody, but nevertheless a cheerful smile. Every round, he got happier, friendlier, as his opponent grew enraged and tired, eventually losing the will to fight” (152). So, “in your worst moments, picture Johnson: always calm, always in control, genuinely loving the opportunity to prove himself, to perform for people, whether they wanted him to succeed or not” (153). Jack Johnson’s will was so impressive, the American novelist Jack London said, “No one understands him, this man who smiles. Well, the story of the fight is the story of a smile. If ever a man won by nothing more fatiguing than a smile, Johnson won today” (153).

DING DING 

Those are just three out of many great examples used throughout Holiday’s book. Since we’re all different, there could easily be other leaders you’d rather use as your own inspiration. You have legendary warriors, political leaders, inventors, and so many more to pick from. If I explained the importance of all of them, this review would become a summary, spoiling the read, ruining the affect the author worked so hard to create. Because after you read this book, you’ll know so much more about yourself. You’ll understand the techniques you already do naturally in your own life and this will help you have confidence in any difficult situation. And then you’ll also discover new strategies, creating your own way to incorporate parts of Stoicism into your life. 

We all have difficult trying times in our lives, and this book helps you approach them with the wisdom of Marcus Aurelius, Amelia Earhart, Jack Johnson, and many more to help you approach any circumstance with the grace and poise of a philosopher. The author even has a chapter he called “Postscript: You’re Now a Philosopher. Congratulations.” Not only that, but there’s a reading list he provides with the best books about Stoicism which he read and due to him reading them, he knows which books to stay away from, making his recommendations the best way to continue educating yourself on Stoicism. The Obstacle Is the Way by Ryan Holiday is a page-turner that’ll improve you as a person in more ways than you could ever imagine.

Thank you for reading our book review about The Obstacle Is the Way by Ryan Holiday. We are not affiliated with the publisher, but here’s the link to pick up a copy.

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E. R. Sanchez is the author of Fried Potato Press’s first young adult thriller, Petaco Dreams, which will be released fall 2023. He also has poems and stories published online and in print. If you’d like to read his work that was published online, please click here to go to his Stories and Poetry Section.

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