I sit down with Jenny Nguyen, founder of The Sports Bra, to talk about what happens when frustration becomes purpose. Jenny shares how one ordinary night watching women's basketball sparked an extraordinary idea, why she finally decided to stop waiting for someone else to build the world she wanted to live in, and how trusting a dream that had never been done before transformed not only her own life, but an entire movement. Together we explore the courage it takes to go first, the people who help carry us up the mountain, and why the smallest acts of belief can create ripple effects far beyond what we ever imagined. We also answer a Dear Sugar letter from a young woman struggling to forgive her parents after their divorce, and reflect on what it means to love imperfect people while making room for grace.

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We sit down with world-record powerlifter Tamara Walcott to talk 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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Sarah Spain joins us 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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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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Kym Hampton was there at the beginning of the Women's National Basketball Association, helping to pave the way for generations of athletes to come. But this conversation isn't just about basketball—it's about how we continue evolving throughout our lives. Kym and I talk about resilience, reinvention, and the quiet power of choosing kindness, even when the path ahead isn't clear. We also answer a Dear Sugar letter from a listener wondering how to handle a complicated work relationship.

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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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Writer and hiker Cara Benson joins us for a deeply personal conversation about grief, addiction, healing, and the solace found in wild places. We explore how hiking helped us navigate profound loss, what it means to keep moving forward when life shatters, and how nature can offer connection, perspective, and comfort when words fail. We also answer a Dear Sugar letter from a woman searching for meaning after a lifetime of caring for everyone but herself.

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Yoga teacher and founder of Yoga with Adriene, Adriene Mishler, joins us for a conversation about courage, self-care, and learning to truly listen to yourself. Adriene reflects on the lessons that emerged from an unexpected panic attack, the importance of showing up imperfectly, and why meaningful change often comes through small, consistent acts of care.

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Olympic gold medalist speed skater Erin Jackson joins us to discuss embracing unexpected opportunities, finding joy in the journey, and navigating life's setbacks. Erin reflects on her improbable rise from roller skating in Florida to Olympic champion, the teammate whose selfless act helped send her to the Olympics, and we answer a Dear Sugar letter about how to keep moving forward when life keeps knocking you down.

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Olympic cross-country skier Julia Kern joins us for a candid conversation about resilience, recovery, and the courage to keep dreaming. Fresh off the Milan-Cortina Olympics, Julia reflects on the highs of making an Olympic final, the heartbreak of falling short of a medal, and the years-long battle with chronic pain that nearly made her walk away from the sport. We'll explore the parallels between athletic setbacks, heartbreak, healing, and the importance of finding joy in the journey.

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