I recently had the honor of hearing Ryan Leak speak live at my company’s annual executive leadership conference. His stage presence, authenticity, and comedic delivery had most of us adding one (or in my case, all) of his books to our digital carts before he was even done with his segment. Chasing Failure arrived first, so let’s dig right in! This book opens with a compelling question:
“What would you do if you weren’t afraid to fail?”

Leak uses Chasing Failure to urge readers to rethink how they approach fear, risk, and ambition. For anyone looking to step outside their comfort zone, this book is a powerful reminder that failure is not the end; it’s often the beginning.
Failure is inevitable and valuable. In Chasing Failure, Leak reframes failure as a necessary step on the path to growth. He shares personal stories and examples of high achievers who embraced failure as a learning tool, challenging readers to do the same.
The book encourages setting bold goals, even when the odds feel stacked against you. Leak’s own journey to try out for an NBA team, despite slim chances, epitomizes the idea of dreaming big.
Resilience is also a major theme of this book. By shifting the focus from avoiding failure to cultivating resilience, Leak provides a roadmap for achieving sustainable success.
As someone who often juggles high-stakes decisions, Chasing Failure reminded me that perfection isn’t the goal – progress is. Leak’s conversational tone and actionable insights make it a motivating read for anyone ready to redefine their relationship with failure.
Whether you’re charting a new career path or pursuing a personal dream, this book is an inspiring guide to embracing fear, taking risks, and finding purpose in the process.
Next up on my Leak reading list is Leveling Up. Come back to the blog for a review soon! Have you read any books by Ryan Leak? If so, let me know what you think!
