The Obstacle Was the Way. Now, It’s a Stoic Coach

You’ve Read the Book. Here’s the Prompt That Makes the Three Stoic Disciplines Work in Real Time

Welcome to Words Into Works. Each week, I share one article that helps you use AI to apply what you learn from nonfiction books. If you’ve ever finished a great book—and struggled to do something with it—this newsletter is for you. Paid subscribers gain full access to every prompt, walkthrough, and live example I’m creating to help turn ideas into action.

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TL;DR

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Obstacles aren’t detours; they’re the training ground. This issue turns Ryan Holiday’s The Obstacle Is the Way and the official Action Guide into a live prompt you can run with any LLM to practice the three Stoic disciplines in real time—perception, action, will—so you move from stuck to steady, one clear answer at a time.

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Most obstacles aren’t dramatic.

They’re the everyday snags that knock your focus sideways and tempt you to stall. The question isn’t whether they show up (that’s a given), but how you meet them when you’re caught off guard.

There’s a book I keep returning to in those moments: The Obstacle Is the Way. Its author, Ryan Holiday, has done more than anyone to make Stoicism practical, and the book’s premise is simple and durable, straight from Marcus Aurelius:

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

The three disciplines, as outlined in the book, are repeatable: Perception, Action, and Will. See what is in front of you without story, act on what you can with process and persistence, and build the inner strength to endure what you cannot change.

Simple to name, harder to master. But repeatable, every time you face resistance.

Today’s issue is about turning Stoic theory into a tool you can actually use, right when life throws you a snag. I’ll show you how to turn the book’s three disciplines into a real-time prompt, ready to deploy the instant you feel yourself getting stuck.

Obstacles Are Not Interruptions; They’re Invitations

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Most of us freeze at the sight of one, paralyzed by story, panic, or anger. But the Stoics offer something sharper: the obstacle is the way. It’s not what happens to you that matters, but how you respond, through perception, action, and will.

• Perception: Train yourself to see things as they are without embellishment, panic, or self-pity. Rockefeller’s coolness in a crisis wasn’t talent; it was practiced objectivity. Every time the market crashed, he looked for the lesson. The skill is in stripping the problem to its facts.

• Action: Obstacles are not moved by wishing or waiting. They yield to persistent, creative action—iteration, process, and adaptability. Action isn’t about heroics. It’s about doing what you can, with what you have, from where you are, again and again.

• Will: When events cannot be changed, the work is internal. Will is the discipline of acceptance—not resignation, but endurance, and even love of what happens (amor fati). Build your inner citadel; let no event rob you of your character or composure.

These disciplines are muscles built by struggle, tested by setbacks, strengthened every time you refuse to flinch. They are practiced, again and again, until, like the king’s boulder in the old Zen story, you begin to see opportunity where others only see a dead end.

Grant forged this lesson in war. Boots planted in mud, smoke thick in the air, he held his position, blocking out the chaos, advancing while others ducked for cover. Decades later, Rockefeller tested it in crisis. When markets buckled, men shouted, and fear spread, he kept his head, studied the wreckage, and moved while others froze.

Master perception, action, and will, and, over time, every obstacle becomes your training ground. But how do you actually master, especially in the moments you need them most?

That’s Where The Stoic Coach Comes In

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Most people hit an obstacle and freeze, complain, or stall. The cost is lost momentum, time wasted, and another cycle of “I wish I’d handled that differently.”

But what if you could turn any obstacle into a live training ground for clarity and forward motion, right when you need it?

That’s the purpose of the prompt you’ll find below.

I built it from two sources: The Obstacle Is the Way and the official Action Guide he created for the Daily Stoic store.

If you’re a long-time reader, you’ll recognize some familiar moves. The principle of separating story from event is also foundational in cognitive behavioral therapy (see my issue on Feeling Good). Whether you call it Stoicism or CBT, the core skill is the same: clarity first, then action.

Here’s how the prompt works:

You Control the Depth. Choose between a Full Session for a deeper reset or an Emergency Version for quick, in-the-moment help. The toggle at the top allows you to decide what you need without pressure to complete every step.

One Question at a Time, Never Overwhelming. The prompt guides you step by step, asking for one answer before moving on. This deliberate pace breaks paralysis and helps you move forward, even if you struggle at the start.

Built-In Support If You Get Stuck. If you don’t know how to answer, the prompt automatically shrinks the question or gives you concrete examples, so you’re never left spinning your wheels.

What stands in the way becomes the way. Put the prompt below to the test, and turn your next obstacle into progress: