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Book Notes: The Obstacle is the Way by Ryan Holiday

3 min readMay 12, 2025

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Turning adversity into advantage with ancient wisdom

“The obstacle becomes the way. Forever and ever and ever.”

I finally got around to reading The Obstacle Is the Way by Ryan Holiday, and I can see why it has become a modern classic in the world of Stoic-inspired personal development.

The Obstacle is the Way book cover

It’s a short, structured, and tightly focused book that takes the core principles of Stoic philosophy — especially those from Marcus Aurelius, Epictetus, and Seneca — and applies them to the challenges we all face in work and life. The idea is simple, but powerful: what blocks our path can become the path. Not despite the obstacle, but because of it.

What stood out to me

1. Perception is everything

The first part of the book — Perception — was by far the one I enjoyed the most. Holiday unpacks how our mindset shapes how we experience setbacks, and how reframing events can literally turn adversity into strength.

“We choose how we’ll look at things. We retain the ability to inject perspective into a situation.”

This section felt particularly actionable. There’s something empowering about being reminded that control over our perception is a skill — one we can cultivate.

2. The power of Will

The final part — Will — also hit home. Especially the chapters on mortality, acceptance, and starting over. These ideas resonated deeply and reminded me that resilience isn’t just about grit. It’s about endurance, inner stillness, and perspective.

“The next step… is this: loving whatever happens to us and facing it with unfailing cheerfulness. It is the act of turning what we must do into what we get to do.”

The reminders to meditate on death (memento mori), to let go of what’s out of your control, and to help others as a way of strengthening yourself — these are timeless and grounding.

3. Action: solid, but less memorable

The middle section — Action — felt a bit repetitive. Chapters are short, often focused on one idea, and can come across as formulaic. That said, it still had valuable lessons around discipline, consistency, and breaking large goals into small, finishable tasks.

My opinion

This is a book I’ll return to — especially when I’m facing uncertainty or need to reset my mindset. It’s one of those rare books that’s both accessible and deeply philosophical, which is what makes it so widely loved.

Is it repetitive at times? Yes. Does it rely heavily on examples from historical figures and entrepreneurs? Also yes. But none of that detracts from its value. In fact, the simplicity of the structure makes the lessons stick.

If you’re into Stoicism, self-development, or just want a mental model for facing challenges without spiraling, The Obstacle Is the Way delivers.

🧩 Best quotes

“The impediment to action advances action. What stands in the way becomes the way.”

“Our perceptions determine, to an incredibly large degree, what we are and are not capable of.”

“Persist and resist.” — Epictetus

“Vires acquirit eundo — We gather strength as we go.”

Should you read it?

If you like authors like Ryan Holiday, Tim Ferriss, or James Clear, this one is a no-brainer.

If you’re facing a tough challenge or transition — read it now.

If you want practical Stoicism without ancient language or too much abstraction — you’ll appreciate it.

More from me at www.carlescarrera.com

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Carles Carrera
Carles Carrera

Written by Carles Carrera

www.carlescarrera.com | Writing mostly about what I learn from books about investing, business, marketing and life in general.

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