God Knows I Want to Break Free

The Obstacle Is the Way: Why Small Wins Matter More Than Grand Victories

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

One of my all time favorite books I always go back to is, for review, is Ryan Holiday’s international bestseller The Obstacle Is the Way. He didn’t just revive ancient Stoic philosophy for modern readers, he revealed something revolutionary about how we achieve meaningful progress. The book is know to have been required reading for athletes, entrepreneurs, and artists seeking a framework for overcoming obstacles and adversities.

But here’s what most people miss: the power isn’t in conquering massive obstacles in single heroic moments. It’s in the accumulation of small wins that transform how we see challenges and, ultimately, ourselves.

Perception Changes Everything

Holiday takes the Stoic point of view that an objective mind, which can “resist temptation or excitement, no matter how seductive, no matter the situation,” can succeed. This isn’t about suppressing emotions, it’s about choosing how you interpret obstacles.

Stoicism focuses on things that can be controlled, let go of everything else and turn every new obstacle into an opportunity to get better, stronger, tougher. The ancient philosophy teaches us that obstacles themselves aren’t the problem, our perception of them is.

When you shift perspective from “this is blocking me” to “this is teaching me,” everything changes. The traffic jam becomes meditation practice. The setback becomes the setup for something better.

The Science of Small Wins

While Holiday draws on ancient wisdom, modern neuroscience validates the power of small wins. Harvard research found that nothing contributed more to a positive inner work life than making progress in meaningful work. If a person is motivated and happy at the end of the day, it’s because they achieved something, however small it was.

Each small win activates your brain’s reward pathways, creating a biological reward system and fascinating feedback loop where each success primes your brain for another.

This is the obstacle-as-opportunity formula in action: you don’t need to conquer the entire mountain today. You need to take the next step, then the next, building momentum through small victories that compound over time.

The Three Stoic Disciplines Applied to Small Wins

Holiday structures his approach around three core disciplines that transform how we engage with obstacles:

Discipline of Perception

See obstacles clearly, without the emotional distortion that makes them larger than they are. When you break massive challenges into smaller, achievable components, what felt impossible becomes merely difficult. What felt difficult becomes doable.

Discipline of Action

As Holiday describes it: “We get to work and we solve the obstacles.” Not through grand gestures, but through persistent action. Small wins accumulate. Each obstacle overcome strengthens your capacity for the next one.

Discipline of Will

This is where most people fail, not in the initial attempt, but in the sustained effort. Research shows that recognizing and celebrating small victories significantly improves motivation, reduces stress, and enhances overall well-being. Will isn’t about powering through, it’s about building the habit of progress.

Finding Happiness in the Process, Not the Destination

Here’s the paradox: when you focus solely on the big goal, you miss the hundreds of small wins along the way. Small daily wins have the biggest impact on emotions and motivation, celebrating progress encourages a supportive atmosphere that maintains motivation.

The Stoics understood this 2,000 years ago. Happiness isn’t found in reaching the summit, it’s found in the satisfaction of taking each step well. In choosing to see obstacles as opportunities.

Every obstacle overcome, no matter how small, is evidence that you’re capable of more than you thought. That’s where sustainable happiness lives: not in avoiding challenges, but in developing confidence through repeated small victories.

The Compounding Effect of Tiny Obstacles Overcome

Charles Duhigg uses the term “small wins” to refer to modest behavior changes that set off a chain reaction of more and better changes. This is Holiday’s philosophy in action: each obstacle you navigate successfully builds your capability for the next one.

The person who can maintain composure during minor setbacks develops the resilience for major crises. The person who finds creative solutions to small problems builds the pattern recognition for breakthrough innovations. The person who celebrates small progress develops the psychological stamina for long journeys.

Breaking Free From the “All or Nothing” Trap

Most people trap themselves in the mental prison of believing that only massive achievements matter. They dismiss small wins as insignificant, waiting for the big breakthrough that never comes because they haven’t built the foundation.

When you have a big mountain to climb, it is often best to break in between the hike or break it into phases. So are problems, best broken down into smaller ones with concrete achievable goals.

The obstacle in front of you right now, is the one you’re avoiding because it seems too small to matter or too large to tackle and thats your opportunity. Not someday when you’re “ready” or when circumstances align perfectly. Now!

Your Next Small Win

Tomorrow morning, identify one obstacle, however small, that you’ve been avoiding. Not the biggest problem in your life. One manageable challenge that you could overcome with focused attention.

Then do what Holiday teaches: apply perception (see it clearly), take action (do something about it), exercise willpower (persist beyond the first attempt). Notice how you feel after. That small satisfaction? That’s your brain’s reward system confirming you’re on the right path.

The obstacle isn’t in your way. The obstacle is the way. The way to discover that you’re more capable than you believed.

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