UBA086 - Bookspiration - The Obstacle Is The Way
Go through the problem, not around it.
In December 2017, I picked up The Obstacle Is The Way, having already read Growth Hacker Marketing and enjoyed Ryan Holiday’s writing. At the time, I was rekindling my love of philosophy, particularly modern interpretations of Stoicism and this book seemed like a good choice.
Since then, I’ve read most of Ryan Holiday’s books, but this one has had the biggest impact. and I’ve applied the core ideas repeatedly in both life and work. During the COVID-19 pandemic, when we suffered a huge loss of revenue and clients I decided to call upon this way of thinking. In the end we threw away the rule book and rebuilt the company and culture again - and with the rebuild came a much more adaptable approach and some of the energy from the early days of Rosie Lee.
One of the things I love about this book, and philosophy in general, is the challenge of rewiring my own thinking - being the operating system and the engineer at the same time. With this book it was mostly about evolving how I process setbacks, so that they can become fuel for progress rather than reasons to stop. Some call this ‘integrating’ the knowledge, where an idea from a book moves beyond theory and into the way you operate daily. The Obstacle Is The Way is one of the books I can confidently say has upgraded my operating system.
The Book
At its core, The Obstacle Is The Way is about perspective - the idea that setbacks, challenges and obstacles aren’t just things to endure, they’re the very thing that leads to progress. Inspired by Stoic philosophy, Ryan Holiday builds on the teachings of Marcus Aurelius, Seneca and Epictetus, translating ancient wisdom into something highly practical for modern life.
The book is structured around three key principles: Perception, Action and Will. Perception is how we choose to see a situation: whether we view obstacles as problems or as opportunities. Action is about responding in the most effective way possible: focusing on what we can do rather than what we can’t. And Will is about resilience: the ability to persist, adapt and find strength in adversity. One of the things I appreciate most about this book is how straightforward and practical it is. Ryan Holiday lays out a clear framework for dealing with challenges in a way that actually helps - by shifting our mindset, making smart decisions and refusing to be paralysed by setbacks.
The Inspiration
What resonated most with me about The Obstacle Is The Way was its ability to reframe how I see setbacks. The idea that an obstacle isn’t something in the way (it is the way!) felt both obvious and radical at the same time. It’s not about avoiding difficulty or waiting for the perfect conditions, it’s about using whatever happens as fuel to move forward.
For me, this became particularly useful during the COVID-19 pandemic. As revenue and clients dropped away, we made a deliberate decision to embrace the disruption rather than resist it. Instead of trying to salvage the old way of working, we used the moment to rethink everything: our structure, our culture and the way we approached projects. In the end, it forced us into a more adaptive, energised way of working - one that wouldn’t have happened without the crisis.
More broadly, the book reinforced something I already believed: you can train your own thinking - the way you process challenges is not fixed. We have enough plasticity in our brains so that we can always evolve, rewire and improve how we think.
The Take Out
The biggest lesson I took from The Obstacle Is The Way is that the way we respond to challenges is entirely within our control. We can’t always dictate what happens to us, but we can decide how we react.
In leadership, creativity and business, this mindset shift is invaluable. When faced with setbacks (whether that’s losing a client, a failed pitch or a team challenge) the natural response is frustration. But if you apply this evolved thinking, the question shifts from “Why is this happening?” to “How can this serve me?”. This change in perspective turns problems into opportunities for growth.
I’ve also found this approach particularly useful in mentorship and team culture. When people hit obstacles, the instinct is often to avoid them, to work around them or to feel stuck. But helping people reframe their challenges, to see them as the raw material for progress, can be transformational. It’s something I’ve passed on to teams, colleagues and even gifted copies of this book to others who I felt would benefit from it.
Conclusion
The Obstacle Is The Way is one of the books I’ve read that has genuinely shaped how I think. It reinforced something I’ve come to believe deeply: challenges aren’t just things to get through, they’re the very things that move us forward, if we let them.
It’s a mindset I try to apply daily, in work and in life. When something goes wrong, when a project stalls, when things don’t go to plan, I pause to remind myself: this isn’t deviating me from my path - this is the path.
Written by Russell.