Narrator: What if the single biggest obstacle standing between you and your most ambitious dreams isn't a lack of talent, resources, or opportunity, but simply the fear of falling short? We are conditioned to see failure as a final verdict, a mark of shame to be avoided at all costs. This fear often leads to a life of quiet compromise, where big dreams are shelved in favor of safe, predictable paths. But what if this entire perspective is wrong? What if, instead of running from failure, we should be actively chasing it?

In his book Chasing Failure, author and speaker Ryan Leak challenges this conventional wisdom head-on. He argues that our obsession with success has blinded us to the profound power hidden within our setbacks. Through a blend of personal experience and insightful analysis, Leak provides a compelling roadmap for reframing failure not as an endpoint, but as the most direct path to growth, purpose, and a truly fulfilling life.

Narrator: The core premise of Chasing Failure is a radical shift in perspective: failure is not an identity to be worn, but an event to be leveraged. Leak argues that the fear of failure is what truly paralyzes potential. As children, we dream without limits, but as adults, the "distance between our dreams and our realities is often intimidating." This gap is filled with the fear of what others will think, the fear of inadequacy, and the fear of the unknown.

Leak’s own journey embodies this principle. For years, he dreamed of playing in the NBA, but the fear of not being good enough kept him from truly trying. At 28, inspired by a chance encounter with his hero, Kobe Bryant, he decided to confront this fear. He told Kobe his new idea: he was going to try out for an NBA team specifically to document the process of chasing an almost-certain failure. Kobe’s simple response—"Yeah, man. Do it."—was the final push he needed. Leak’s subsequent journey to try out for the Phoenix Suns, though it didn't land him a contract, taught him a crucial lesson. He realized that chasing failure took him further than chasing success ever did. It forced him to grow, to face his limitations, and ultimately, it opened doors to a new career in leadership coaching, where he now works with NBA teams. The book posits that this is the true purpose of failure: it is not meant to define you, but to refine you.

Narrator: While the book champions chasing failure, it cautions against blind persistence. The mantra "never give up" can be destructive if you're climbing the wrong ladder. Leak introduces a critical framework for discernment called the "Sweet Spot Matrix," which helps evaluate whether a dream is worth the chase. The sweet spot is the intersection of four key elements: Passion, Skillset, Opportunity, and Purpose.

The story of former U.S. Secretary of State Condoleezza Rice perfectly illustrates this. From the age of three, Rice’s life was dedicated to becoming a world-renowned concert pianist. But at a music festival at age seventeen, she was surrounded by child prodigies who possessed an innate talent she knew she could never match. Instead of stubbornly clinging to a dream that was no longer viable, she made the difficult decision to pivot. She walked into a class on international relations and discovered a new passion that aligned with her formidable intellect and strategic mind. Rice didn't fail; she strategically abandoned one dream for a better one that was in her sweet spot. This, Leak argues, is the essence of "never give up-ish"—having the wisdom to know when a failure is a dead end versus when it's a redirection toward your true purpose.

Narrator: The allure of a big goal—becoming a millionaire, gaining a million followers, selling a million books—often obscures the true price of admission. Leak stresses the importance of "counting the cost" before embarking on a major pursuit. This isn't just about financial investment; it's about understanding the required time, discipline, knowledge, and relationships.

He tells the story of Ben Peters, an entrepreneur who decided to invest in an Airbnb property. Peters did everything right. He spent months on data analytics, forecasting, and research before purchasing a home in Minneapolis. Initially, his venture was a resounding success, with the property booked solid. He had counted the cost and paid it. However, he couldn't have predicted the dual impact of the COVID-19 pandemic and the George Floyd riots, which decimated the travel industry in his city. His business failed.

This story isn't a cautionary tale against trying; it's a realistic look at the nature of risk. Even with perfect preparation, external factors can lead to failure. The key, Leak explains, is to ask yourself beforehand: "Are you willing to pay for something now that could fail but will give you what you need to succeed later?" Peters lost his investment, but he gained an invaluable education in real estate and crisis management that better equipped him for his next venture. Counting the cost means accepting that failure is a possible outcome, and viewing that potential loss as tuition for future success.

Narrator: Practical setbacks are only half the battle; the emotional fallout can be even more debilitating. Leak identifies shame as one of the most powerful inhibitors of progress. Shame tells you not that you experienced failure, but that you are a failure. To combat this, he advocates for self-compassion, which he defines not as making excuses, but as recognizing your own humanity when you fall short.

Beyond shame, there is the fear of criticism and rejection. Leak proposes a three-step method for processing feedback: Evaluate, Extricate, and Employ. First, evaluate if the criticism is valid. Second, extricate the helpful parts from the discouraging tone. Finally, employ that information to make concrete improvements. This process is powerfully demonstrated by Jia Jiang, an entrepreneur who was crushed by an investor's rejection. To overcome his fear, he embarked on "100 Days of Rejection Therapy," intentionally seeking out rejection by making absurd requests, like asking to be a greeter at Starbucks. He discovered that rejection rarely had the sting he imagined and that by leaning into it, he could often turn a "no" into a "yes." By befriending rejection, he became immune to its power, a crucial step in any ambitious journey.

Narrator: Ideas are powerful, but as Leak states, they are "not as powerful as your habits." Inspiration is fleeting, but consistent action is what builds momentum. Procrastination is often just fear in disguise, and the best way to conquer it is to break down overwhelming goals into small, daily wins. The book encourages readers to focus on getting just one percent better each day, because extraordinary people are simply those who do consistently what ordinary people do occasionally.

However, self-discipline has its limits. Leak emphasizes that goals have a much higher chance of success when you involve others. Citing a study by the American Society of Training and Development, he notes that you have a 65 percent chance of completing a goal if you simply tell someone. That number skyrockets to 95 percent if you have a specific accountability appointment with that person. Whether it's a friend who checks in on your workout goals or a mentor who holds you to a business deadline, creating a system of external accountability makes it "embarrassingly difficult" to give up. You are not meant to chase failure alone; building a supportive community is a non-negotiable part of the process.

Narrator: Perhaps the most dangerous time for any person or organization is right after a major success. Success can breed complacency and a fear of losing what has been gained. Leak argues that in a rapidly changing world, "the only strategy that is guaranteed to fail is not taking risks." He points to the classic case of Blockbuster, which, at the height of its success, laughed Netflix's founders out of the room when they offered to sell their fledgling DVD-by-mail company for $50 million. Blockbuster was afraid to risk its profitable late-fee model and failed to adapt, leading to its bankruptcy. Netflix, in contrast, has consistently taken strategic risks, from streaming to original content, ensuring its continued dominance.

Leak encourages readers to continue taking calculated risks even after achieving success, focusing on three areas: strategic risks (like Beyoncé’s surprise album release), financial risks (like Amazon’s massive R&D budget), and people risks (giving opportunities to unproven but promising individuals). The goal is not to be reckless, but to understand that growth and failure are two sides of the same coin. If the size of your failures isn't growing, you're not inventing at a scale that can truly make a difference.

Narrator: The single most important takeaway from Chasing Failure is that failure is not the opposite of success; it is an integral component of it. The book systematically dismantles the fear-based mindset that keeps so many people from pursuing their potential and replaces it with a practical, courageous, and ultimately more effective approach to life and work. It teaches that by embracing setbacks, we gain resilience, wisdom, and unexpected opportunities.

Ultimately, Ryan Leak leaves us with a profound challenge. He tells the story of his friend Liz, who, despite battling cancer, ran three miles in the rain just to help him move. Her life was a testament to showing up, to acting on good intentions today, not tomorrow. The book asks: Who is on the other side of your dream, waiting for you to be brave enough to chase it, to risk failure for a purpose greater than your own comfort? Don't wait for the perfect moment. The time to start is now.