S1 EP16 Ryan Woodruff - Why High Achievers Burn Out—and What Comes Next
What happens when success no longer feels like enough? In this episode of Winning Twice, Austin Cheviron sits down with leadership and performance coach Ryan Woodruff to explore the transition from chasing achievement to building a life of purpose, impact, and legacy. Ryan shares his journey from a 30-year corporate leadership career and executive role to walking away from a high-paying job in search of something more meaningful. Together, they unpack the realities of burnout, entrepreneurship, coaching, and the difficult process of discovering what you're uniquely equipped to offer the world. Along the way, they discuss why video games taught them lessons about strategy, leadership, optimization, and decision-making, how coaches should identify the one thing they do exceptionally well, and why simplifying your message often leads to greater impact. Whether you're building a business, considering a career pivot, or trying to create a life aligned with your values, this conversation offers practical wisdom on finding conviction, serving others, and ultimately winning twice—both professionally and personally.
Winning Twice is a podcast about building a life where success shows up in both business and at home. Hosted by Austin Cheviron, the show features real, unfiltered conversations with high performers about money, time, leadership, and legacy—designed to help you win professionally without losing what matters most personally.
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