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The Obstacle Is the Way
The Timeless Art of Turning Trials into Triumph
Ryan Holiday
Philosophy & Stoicism

The Obstacle Is the Way: Turning Trials into Triumph

by Ryan Holiday

11 min read Updated Dec 2026 Stoicism

The Three Disciplines

  • Perception: How we see and understand what happens around us. This is entirely within our control. We choose to see obstacles as threats or opportunities.
  • Action: The energy and creativity we bring to problems. Directed, disciplined action—not frantic activity—is what transforms obstacles into opportunities.
  • Will: The inner power to accept what we cannot change. The citadel of resilience that allows us to endure and even thrive amid hardship.
  • The obstacle becomes the way. What stands in the path becomes the path. The impediment to action advances action.
  • Amor Fati: Love your fate. Not merely accept what happens, but embrace it—because it is the raw material from which you will build your success.

The Ancient Philosophy for Modern Problems

Nearly two thousand years ago, Roman Emperor Marcus Aurelius wrote in his journal: "The impediment to action advances action. What stands in the way becomes the way." This single idea—that obstacles are not obstacles at all, but rather fuel for growth—forms the foundation of Ryan Holiday's modern Stoic masterpiece.

Holiday draws on examples from history, business, sports, and warfare to show that the most successful people don't avoid obstacles—they use them. From John D. Rockefeller to Amelia Earhart, from Abraham Lincoln to Steve Jobs, the pattern is the same: obstacles become advantages for those with the right mindset.

"The impediment to action advances action. What stands in the way becomes the way."
— Marcus Aurelius

This book is not about positive thinking or pretending problems don't exist. It's about a practical methodology for turning every challenge into an opportunity for growth, advancement, and ultimately, success. The Stoics called this the art of turning trials into triumph.

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Discipline 1: Perception

The first discipline is controlling how you perceive obstacles. Events are objective; our interpretation of them is subjective and entirely within our control. Most people see obstacles and freeze. They panic. They react emotionally. The Stoics teach us to do the opposite.

The Power of Objectivity

When John D. Rockefeller was a young man, the Panic of 1857 destroyed the American economy. While others saw catastrophe, Rockefeller saw education. He watched the market carefully, learning lessons about fear and greed that would serve him for the rest of his life. He later said the panic was one of the most formative experiences of his business career.

This is the power of perception: where others see disaster, you can choose to see opportunity. Where others see an ending, you can see a beginning.

Steady Your Nerves

The first step in perception is controlling your emotions. Not suppressing them—that's impossible—but not being controlled by them. When you feel the panic rising, take a breath. Step back. See the situation for what it really is, not what your fear tells you it is.

  • Objectivity: See what is, not what you fear
  • Control emotions: Remove panic from the equation
  • Find opportunity: Every obstacle contains hidden advantages
  • Alter perspective: Is it really as bad as it seems?

Finding the Opportunity

Every obstacle contains opportunities. The Stoics believed this firmly. A stuck door can teach you about patience, or force you to find a window. A lost job can lead to a better one. The key is looking for the opportunity instead of fixating on the problem.

Discipline 2: Action

Seeing clearly is not enough—you must act. But action must be persistent, deliberate, creative, and flexible. The Stoics were not passive philosophers. They were men and women of action who accomplished remarkable things precisely because they had the right philosophy.

Persistence and Iteration

Thomas Edison failed thousands of times before inventing the lightbulb. Each failure taught him something. Each obstacle refined his approach. Obstacles are not stop signs—they're guides. They show you what doesn't work so you can find what does.

This is the essence of persistence: not blind repetition, but intelligent iteration. You try, you fail, you learn, you adjust, you try again. Each attempt gets you closer to success.

Use Obstacles Against Themselves

Like a jiu-jitsu master who uses an opponent's strength against them, you can use obstacles against themselves. Got rejected from a university? Use that chip on your shoulder as motivation. Lost a competition? Let it fuel your training for the next one.

  • Get moving: Start somewhere, anywhere
  • Practice persistence: Keep pushing when blocked
  • Iterate: Try, fail, learn, adjust
  • Follow the process: Focus on the next step, not the destination
  • Do your job: Focus on what's in your control
"Action is the answer. What we need is action—directed action, constrained action, bold action. Movement is what we're after. The path is made by walking."
— Ryan Holiday

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Discipline 3: Will

Some obstacles cannot be overcome through perception or action alone. Some circumstances are truly insurmountable—at least in the short term. These require will—the inner power to endure what we must with grace and resilience.

The Inner Citadel

The Stoics spoke of an "inner citadel"—a fortress within yourself that cannot be touched by external events. Viktor Frankl, a Holocaust survivor, demonstrated this when he wrote that everything can be taken from a person except one thing: the freedom to choose one's attitude in any given circumstances.

This is the ultimate power of will: no matter what happens to you externally, you control your inner response. You choose how to interpret events. You choose whether to give up or keep going. You choose who you become through hardship.

Prepare for Adversity

The Stoics practiced "premeditatio malorum"—the premeditation of evils. They would imagine worst-case scenarios not to be pessimistic, but to be prepared. When you've already mentally rehearsed the worst, you're not surprised when difficulties arise.

  • Accept what you cannot change — Don't fight the unchangeable
  • Prepare for difficulties — Pre-meditate challenges
  • Amor fati: Love your fate, even the hard parts
  • Persevere: Endure with grace and purpose
  • Find meaning: Use suffering as fuel for growth

Amor Fati: Love Your Fate

The ultimate expression of will is "amor fati"—love of fate. Not merely accepting what happens, but embracing it. Seeing everything that occurs as necessary and even good. This doesn't mean you can't try to change things. It means you love the process, including the obstacles.

"My formula for greatness in a human being is amor fati: that one wants nothing to be different, not forward, not backward, not in all eternity."
— Friedrich Nietzsche

The Stoic Path Forward

The Stoics didn't avoid obstacles—they used them. They understood that the path to greatness runs through difficulty, not around it. Every setback is a setup for a comeback, if you have the right philosophy.

This isn't about being blindly optimistic. It's about being realistically prepared. It's about seeing clearly, acting decisively, and enduring gracefully. It's about turning what would break others into what makes you stronger.

The next time you face an obstacle, remember: this is not something to be avoided. This is the raw material from which you will forge your success. The obstacle is the way.

"It's not things that upset us, it's our judgment about things."
— Epictetus
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