The Obstacle Is the Way - Ryan Holiday

This note now includes my notes on Courage Is Calling (November 2023).

Ryan Holiday's The Obstacle Is the Way draws on Stoic philosophy to argue that we can change how we see adversity, and in doing so turn obstacles into opportunities. The book is organised in three parts: perception, action and will.

Control what you can

One of the quotes that stayed with me most is: "What is up to us? Our emotions. Our judgments. Our creativity. Our attitude. Our perspective. Our desires. Our decisions. Our determination." It sums up the Stoic principle that our power lies in what we control. In a world where people habitually complain about their circumstances, the book's advice is that "focusing exclusively on what is in our power magnifies and enhances our power."

Perception

"When you worry, ask yourself, 'What am I choosing to see right now?'" Holiday advises. Worry takes a toll on your wellbeing and hands your judgement over to passing problems. Holiday points to Marcus Aurelius, the Stoic philosopher and Roman emperor, who simplified complicated situations by describing them plainly, stripped of their ornament. Seen that way, life becomes less about reacting to what happens to us and more about how we interpret and respond to it.

Action

Holiday doesn't only offer theory; he gives practical advice. "Persist and resist" was a phrase Epictetus favoured: keep going, and resist distraction and discouragement.

Will

"True will is quiet humility, resilience, and flexibility," Holiday writes, countering the idea that Stoicism means having no emotions.

He also quotes the American abolitionist Wendell Phillips: "What is defeat? Nothing but education; nothing but the first step to something better." It captures the Stoic view of challenges as steps towards improvement.

The book ends with amor fati, a love of one's fate. The goal isn't mere acceptance but to feel "great about it", as Holiday puts it: "Because if it happened, then it was meant to happen, and I am glad that it did when it did. I am meant to make the best of it."

It also reminds us that "being trapped is just a position, not a fate."

What I took from it

The Obstacle Is the Way is a practical guide to coping with what life throws at you. Whether you already practise Stoicism or are new to it, it's useful for anyone who wants to spend less energy on what they can't control and more on what they can.

Also: Courage Is Calling

Courage Is Calling: Fortune Favors the Brave is the first book in Holiday's series on the four Stoic virtues. It weaves stories of courage from history together with practical advice.

The book is about fear and courage. Feeling fear is human; acting in spite of it is what counts. Holiday argues that the true measure of our lives isn't whether we avoid fear but whether we keep pursuing virtue despite it. A life without challenges is untested, and character shows not only in grand heroic acts but in the everyday choices that define us.

Two points stayed with me. First, courage isn't a lofty ideal reserved for a few; it's something anyone can build. Second, values guide us: the stories in the book show how values pull us towards our goals and shape the path we take, and taking responsibility for our actions is part of self-respect and of living with courage.

Read together, the two books make the same demand from different sides: see clearly what is in your control, and then have the courage to act on it.