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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