Maddy Schaffrick joins Cheryl for a deeply personal conversation about identity, resilience, and rediscovering purpose. Maddy reflects on becoming a professional snowboarder at just 14, the pressure and injuries that led her to retire at 20, and how she rebuilt her life afterward. She discusses what it's like to go from teen prodigy to burning out and how coaching young athletes helped her discover a new mindset rooted in self-belief rather than external validation. Together they explore the importance of finding your “why,” navigating self-doubt, and learning how to fall and get back up, both on and off the mountain.

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Iditarod musher and bestselling author Blair Braverman joins Cheryl for a conversation about risk, resilience, and the deep bond between humans and animals. She shares what it’s like to navigate blizzards, isolation, and uncertainty all while being guided by her dogs. Together, they explore fear, leadership, and how trust is built not through control, but through genuine connection.

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For Sarah Outen, adventure has meant rowing across oceans alone and navigating some of the most remote places on earth. She joins Cheryl to reflect on the risks she’s taken, the failures she’s faced, and the resilience she’s built along the way. Together, they explore endurance, self-trust, and the question at the heart of every journey: what are you really searching for?

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Cheryl talks with racing legend Katherine Legge about discipline, focus, and the mental strength required to compete at the highest level of racing. Katherine reflects on setbacks, persistence, and carving out space in a male-dominated sport. Together, they explore what it means to hold your ground, even when everything is pushing against you.

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Soccer icon Abby Wambach joins Cheryl Strayed to explore the inner life behind extraordinary achievement. Abby reflects on the relentless drive that fueled her legendary career, the complicated relationship between success and self-worth, and the emotional journey of redefining identity after elite sports. Together, they discuss grief, sobriety, partnership, and what it means to live with both humility and audacity. The episode ultimately asks a powerful question: how do we measure a meaningful life once the medals are won?

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Sarah Spain joins Cheryl for a conversation about nonlinear careers, unexpected pivots, and trusting that the path will reveal itself to you. From comedy to ESPN, Sarah reflects on saying yes before she felt ready and what happened next.

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Cheryl talks with ultra runner and human rights lawyer Stephanie Case about what happens when passion, purpose, and motherhood collide. Stephanie reflects on returning to racing after infertility and pregnancy loss, the viral moment when she breastfed her daughter mid-race, and how movement helps her process some of the hardest work in the world.

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In Episode 3 of Mind Over Mountain, Cheryl talks with record-setting long-distance hiker Heather Anderson about curiosity, courage, and the quiet power of putting one foot in front of the other. Heather shares how she went from a non-athletic kid to setting speed records on America’s longest trails and what hiking has taught her about fear, resilience, and finding your way forward.

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