Book 48 of 52: The Obstacle Is The Way by Ryan Holiday

Book 48 of 52: The Obstacle Is The Way by Ryan Holiday

April 23, 20254 min read

Curious about how I used lockdown as a chance to jumpstart two major Bucket List items? Dive into my full journey here: Read the full blog

Book 48/52 of My #52Books52Weeks Bucket List Challenge

I’ll be honest—there was something about Ryan Holiday’s writing style that didn’t quite gel with me. It didn’t flow as well as I expected. But that said, the front cover says it all:
👉
The obstacle in the path becomes the path.

This book is based on Stoicism, the ancient Greek philosophy that teaches us to embrace obstacles, control what we can, and let go of what we can’t. The core message? Challenges are not setbacks—they’re stepping stones.

Even though I found the writing a bit heavy at times, the principles in this book are solid. If you’re someone who wants to develop mental toughness, resilience, and grit, then The Obstacle Is The Way is a must-read.

What is Stoicism?

Stoicism is an ancient philosophy that teaches:
Control what you can, accept what you can’t.
See obstacles as opportunities.
Detach from emotions that don’t serve you.
Take action despite fear, doubt, or setbacks.

Marcus Aurelius, Seneca, and Epictetus were some of the original Stoic thinkers—and their teachings still apply today, whether in business, sports, or life.

8 Key Takeaways from The Obstacle Is The Way

1️⃣ Perception, Action, Will – The Stoic Framework

  • Perception: How you see the problem.

  • Action: How you respond to the problem.

  • Will: How you endure and push through it.

Change your perspective, take calm & deliberate action, and have the inner strength to persist. That’s how you turn obstacles into opportunities.

2️⃣ You Control How You See Things

  • You can’t control what happens—but you can control how you respond.

  • Instead of panicking, step back and see the obstacle objectively.

  • Detach from emotions and focus on facts.

3️⃣ Take Action – Even If It’s Imperfect

  • Action beats analysis paralysis.

  • Fail fast, fail forward, and keep moving.

  • Perfectionism stops progress—just take the next step.

4️⃣ Fear is a Sign to Move Forward

  • What we fear the most is often what we need to do the most.

  • If something scares you, lean into it instead of running away.

  • Fear is a signal, not a stop sign. 🚦

5️⃣ The Power of Persistence & Grit

  • Endurance is more important than talent.

  • Most people quit when things get hard—winners keep going.

  • If you want uncommon results, you need uncommon resilience.

6️⃣ Turning Pain into Strength

  • Every struggle builds character—if you let it.

  • See adversity as an opportunity to grow rather than a setback.

  • What you go through will become your greatest asset later.

7️⃣ Expect & Embrace Setbacks

  • Problems are part of the game—expect them.

  • Instead of resisting challenges, welcome them as teachers.

  • You can’t change reality, but you can change your response to it.

8️⃣ Amor Fati – Love Your Fate

  • Amor Fati means “love your fate”—embrace everything, good or bad.

  • Instead of wishing things were different, accept and make the most of them.

  • Every obstacle contains hidden advantages if you choose to see them.

How This Relates to Living Your Bucket List Life

If you want to live a Bucket List Life, you’re going to face challenges. That’s just part of going after big goals. But as this book teaches, obstacles aren’t roadblocks—they’re part of the journey.

✅ Want to build a business? Expect failures along the way.
✅ Want to travel the world?
You’ll deal with setbacks, delays, and detours.
✅ Want to write a book?
Prepare for writer’s block and doubt.

Instead of getting frustrated when things don’t go to plan, use Stoicism to reframe the situation: “This is making me stronger.”

While the writing style didn’t fully click with me, the principles in this book are gold. If you want to develop mental toughness, resilience, and the ability to thrive under pressure, then The Obstacle Is The Way is a book worth reading.

Who else has read this? How has Stoicism helped you in life or business? Drop a comment & let me know! 👇

Stay tuned for Book 49 of 52 as I continue this adventure of learning and growth!

#BucketListLife #UltimateChallenge #52Books52Weeks


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Trav Bell - The Bucket List Guy is the World's No1 Bucket List Expert. He & his global tribe of Certified Bucket List Coaches® are on a mission to help 10 million Bucket Listers to #tickitB4Ukickit.

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