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Molly’s top-rated podcast will help you reimagine how you live, lead and work. Each episode showcases game-changing athletes, coaches, entrepreneurs and thought leaders.
Molly’s top-rated podcast will help you reimagine how you live, lead and work. Each episode showcases game-changing athletes, coaches, entrepreneurs and thought leaders.

Episode 48- Ryan Holiday on How to Turn Obstacles into Advantages

The New York Times calls him “a sought-after guru to NFL coaches, Olympians, hip-hop stars and Silicon Valley entrepreneurs.” Ryan Holiday is a marketing expert who made a name for himself as the director of marketing for American Apparel and has gone on to work with clients like Google, Tony Robbins and Tim Ferriss. He’s the bestselling author of The Obstacle Is the Way and Ego Is the Enemyand his books have sold more than 1.3 million copies. On this episode, Ryan shows us how to turn even the most insurmountable obstacles into advantages. We talk about what we can learn from the ancient philosophy of stoicism, the power of staying present, and why most of our failures are self-inflicted.

Follow Ryan: Twitter | Facebook | Instagram | Website

Show Notes

  • How he decides what book projects to pursue (2:00)
  • The core principles of stoicism (3:18)
  • How Ryan first embraced the ancient philosophy of stoicism and how it applies to our world today (4:25)
  • Ryan Holiday’s following in the sports world and the hunger to gain a mental edge (6:02)
  • The relentless focus on improvement as a wall against ego (9:06)
  • Fearlessness stays present (11:57)
  • The discipline of managing your energy (13:00)
  • How to turn a setback into a pathway forward (14:30)
  • The discipline of perception: “it’s not things that upset us; it’s our judgment about things.” (19:28)
  • Why purpose is a more important driver than passion (22:33)
  • Purpose is passion at a directed level (24:18)
  • The things we control: our reactions, our thoughts, our emotions, the ability to change direction (26:25)
  • A defining moment in Ryan’s life (29:23)
  • A reminder he uses to stay present in the moment (33:10)

Resources / People Mentioned

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In a world fixated on fleeting success, a bold framework for pursuing your goals unapologetically without compromising what matters most. This isn’t just another self-help theory: Dynamic Drive is your practical guide to unlocking your true potential. Through her decades of experience working with top athletes and peak performers across industries, renowned keynote speaker and leadership expert Molly Fletcher has created a proven formula backed by research that outlines the seven keys to sustainable success. The truth is fulfillment doesn’t come from setting and accomplishing goals in isolation. It comes from Dynamic Drive—a holistic approach that connects all parts of you with your purpose and allows you to engage in meaningful growth, both personally and professionally. Unlike traditional approaches that dilute drive into a mere means to an end, which can lead to burnout, Dynamic Drive is a way of life, a mindset. It’s about figuring out the parts of your life where you are playing small or safe or are dissatisfied. Dynamic Drive is the process by which we implement and sustain intentional change. The greatest reward isn’t in what you achieve, but who you become in the process. Your path to sustained high performance in all areas of your life begins here. This is your manual for an aligned, joyful, and relentless pursuit of a better you.
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#1 Worldwide Bestselling Author of
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