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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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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Cheryl Strayed sits down with champion ultrarunner and obstacle racing pioneer Amelia Boone to talk about endurance, identity, and redefining strength. From pioneering obstacle racing to embracing vulnerability through eating disorder recovery, Amelia reflects on pain and what it means to honor her body now without shame.

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Cheryl Strayed talks with world-record powerlifter Tamara Walcott about strength in every sense of the word. Tamara shares her journey from being picked last to lifting record-breaking weight, the difference between motivation and dedication, and how she replaced shame with pride. Plus, they offer advice to a mom struggling with guilt around taking time for herself—and why saving your own life sometimes starts with one rep.

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