Why I Read The Obstacle Is the Way
When I first surrendered to the federal prison in Montgomery, I did what a lot of men do in here—I stared at the wall and asked, How did I end up here?
For someone who once ran a thriving business, employed dozens of people, and lived a life most would consider successful, losing my liberty hit me like a freight train. I had gone from negotiating multi-million-dollar deals and manufacturing equipment overseas to waiting in line for chow and trying to navigate a system designed to wear you down.
But I didn’t want to waste my time pointing fingers or making excuses. I knew I had to get back to what I’ve always done best: solve problems.
That mindset is exactly why I picked up The Obstacle Is the Way by Ryan Holiday.
I was already familiar with Stoic philosophy from years in business, but I’d never seen it broken down so clearly—or so practically. I’d heard other men inside mention the book as something that “shifts your mindset.” They were right. I read it in a few days, but I’ve thought about it every day since.
What I Learned From Reading This Book
Holiday builds the book around a single powerful idea: what stands in the way becomes the way. In other words, our greatest challenges aren’t blocks—they’re building materials.
He pulls from the teachings of ancient Stoic philosophers like Marcus Aurelius, Seneca, and Epictetus, but presents their lessons in a modern, straightforward voice. There’s no fluff here. Just timeless principles applied to real-world situations: failure, loss, injustice, pain.
He breaks the approach down into three parts—Perception, Action, and Will—and each one helped me frame this season of my life in a more productive light.
Perception: Holiday talks about the power of reframing a challenge. A setback is only a setback if we let it define us. That clicked immediately for me. I could see how my own decision to possess firearms, despite my prior felony, was more than a legal mistake—it was a failure of judgment, of foresight. But it doesn’t have to be the end of my story.
Action: Instead of freezing or folding, Holiday urges readers to take purposeful steps, even small ones, even from impossible places. That’s what I’ve tried to do inside—writing lesson plans for Prison Professors, mentoring guys like DeShawn, and turning my experience into something that helps others.
Will: The hardest one. Will is about accepting the things you can’t control while still choosing your response. I can’t control how long my sentence will be. I can’t control how the system treats me. But I can control how I use this time—and that’s what I focus on every day.One of the lines that stuck with me most was this:
“Blessings and burdens are not mutually exclusive.”
I read that sentence a dozen times. Because here I am—in prison—yet more connected to purpose than I’ve been in years. That paradox is the essence of Stoicism. It’s not about pretending bad things are good. It’s about asking, What can I build from this?
How the Book Will Contribute to My Life Upon Release
This book didn’t just help me get through a hard moment. It gave me a system for moving forward.
When I walk out of here, I know it won’t be easy. I’ll carry a criminal record, lost time, and a complicated story. But thanks to The Obstacle Is the Way, I’ll also carry a mindset that sees those challenges as fuel, not friction.
I plan to continue the work I started in here—teaching others, building tools for incarcerated individuals, and creating business frameworks that show people how to solve real problems with limited resources. I want to help others realize that even when the world sees you as a failure, you can still produce value. You can still lead.
Holiday’s book reinforced what I already believed: I’m not done yet.
My fall is part of my foundation.
The obstacle isn’t in the way.
It is the way.
