4 Amazing Book Takeaways from “The Obstacle is the Way”

“The impediment to action becomes the action. What stands in our way becomes the way.”
Marcus Aurelius

If you’ve never read a Ryan Holiday book, I highly recommend you do. He’s got an simplistic writing style that lays out information in a way that’s thought-provoking, easy to interpret and addictive to read. In his book, The Obstacle is the Way, Ryan takes us through some principles of Stoic philosophy by weaving together a series of stories that summarize that the best mindset for a high performance life is one that adapts and embraces challenge. Below I’ve listed which topics the book covers and have selected 4 of my favorite principles to dive into with excerpts from the book.

Book Structure:
There are 3 main areas of focus (Perception, Action & Will) with around 7-8 sub-sections. Here are the areas from the book:

• To be objective
• To control emotions and keep an even keel
• To choose to see the good in the situation
• To steady our nerves
• To ignore what disturbs or limits others
• To place things in perspective
• To revert to the present moment
• To focus on what can be controlled

• Energy
• Persistence
• Cohort and deliberate process
• Iteration and resilience
• Pragmatism
• Strategic vision
• Craftiness and savvy
• An eye for opportunity and pivotal moments

• Always prepare ourselves for more difficult times
• Always accept what we’re unable to change
• Always manage our expectations ‘always persevere
• Always learn to love our fate and what happens to us
• Always protect our inner self, retreat into ourselves
• Always submit to a greater, larger cause
• Always remind ourselves of our own mortality


Be Objective:

“The perceiving eye is weak, he wrote, the observing eye is strong” -Samurai Swordsman, Miyamoto Musashi.

“Objectivity means removing “you” – the subjective part – from the question. Just think, what happens when we give them advice? Their problems are crystal clear to us, the solutions obvious. Something that’s present when we deal with our own obstacles is always missing when we hear other peoples problems: the baggage”

Action: get Moving (energy)

“We jog when we should be running or, better yet, sprinting. And we’re shocked – shocked! When nothing big ever happens, when opportunities never show up, when new obstacles begin to pile up, or the enemies finally get their act together”

“While overpaid CEOs take long vacations and hide behind email auto responders, some programmer is working eighteen hour days coding the start-up that will destroy that CEO’s business. And if we were honest, we’re probably closer to the former than the latter when it comes to the problems we face (or don’t face.”

“Those who attack life with the most iniatitive and energy usually win”

Always submit to a greater, larger good.

“Shared purpose gives us strength”

“Stop making it harder on yourself by thinking about I, I, I. Stop putting that dangerous “I” in front of events. I did this. I was so smart. I had that. I deserve better than this. No wonder you take losses personally, no wonder you feel so alone. You’ve inflated your own role and important. Start thinking: Unity over Self. We’re in this together.”

“Embrace this power, this sense of being part of a larger whole. It is an exhilarating thought. Let it envelop you. We’re all just humans, doing the best we can. We’re all just trying to survive and in the process inch the world a forward a little bit.”

“Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger.”

Remind ourselves of our own mortality

“Death doesn’t make life pointless, but rather purposeful”

“… thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because its invigorating”

“Reminding ourselves each day that we will die helps us treat our time as a gift.

This book provided some simple yet profound principles to put into practice. I hope you enjoyed these takeaways. Let me know if you’d like to see more book takeaways by shooting us a message on the contact page.

To the good life!


About the Author


Max is the founder of BEAR SQUEEZE. He is obsessed with nutrition, fitness and discovering new ways to improve performance. Max lives in Los Angeles and in his spare time you can find him surfing along the pacific coast.

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