Our book series continues with The Obstacle Is the Way by Ryan Holiday.
The book draws from the ancient philosophy of Stoicism and centers on a simple idea. The obstacles we face in life are not just things to get around. Often, they’re the path forward.
In this episode, we break down the core ideas from the book. We talk about why the way we perceive obstacles matters more than the obstacle itself, when persistence is useful, and when resistance might actually be a signal to change direction.
Greg also shares how this book impacted him personally during one of the hardest seasons of his life and why the ideas around perspective and perseverance have stayed with him for nearly a decade.
If you’ve ever faced something difficult and wondered whether to keep pushing forward or pivot entirely, this conversation (and this book) offers a helpful lens to think about obstacles.
Because sometimes the thing standing in your way is actually pointing the way forward.
What We Talked About
• The Stoic philosophy behind The Obstacle Is the Way
• The three disciplines Ryan Holiday highlights: perception, action, and will
• Why the way we interpret obstacles shapes how we experience them
• The tension between perseverance and recognizing when it may be time to pivot
• Why action creates momentum when you're facing resistance
• Historical examples from leaders like Theodore Roosevelt and Abraham Lincoln
• A real example from our own UNBLOCK Yourself program about pushing through discomfort and eventually finding the right lane
We hope you enjoy this episode!
EPISODE LINKS & REFERENCES
Book Featured in This Episode
The Obstacle Is The Way by Ryan Holiday
The Painted Porch Bookshop (Ryan’s bookstore in Texas)
We’d love to connect with you. Here’s where to find us:
Subscribe to Vienna Five Newsletter
On this podcast, we explore what it means to get UNBLOCKED.
You’ll hear stories about finding clarity, navigating career pivots, and choosing to live with intention. Sometimes that’s through conversations with guests who made bold moves and changed direction. Other times it’s just the two of us unpacking the books, ideas, and lessons shaping our own journey.
We’re not experts looking down from a stage. We’re in it too. Building, questioning, adjusting, and trying to create lives that feel more aligned, more alive, and more intentional.
