This week we talk to trailblazing polo player Shariah Harris to discuss resilience, identity, and the unexpected journey that led her from a chance encounter with horses in Philadelphia to making history as the first Black woman to compete at the highest level of the U.S. Women’s Polo Championship. Shariah reflects on growing up through the Work to Ride program, navigating predominantly white spaces in elite sports, and balancing the demands of being both a professional athlete and an operating room nurse. Together, we explore the lessons horses can teach us about patience, courage, and trust — and what it means to pave the way for the next generation while staying grounded in your love for the sport.

See omnystudio.com/listener for privacy information.

Olympic heptathlete Chari Hawkins opens up about what it really feels like to keep going when everything falls apart. What begins as a reflection on Chari’s career unfolds into something much more vulnerable—her struggles with identity, the quiet devastation of missing the Olympic team, and a moment where she wasn’t sure she wanted to keep going at all. Together, we explore fear, failure, and the small, brave decisions that shape a life. Our Dear Sugar letter this week touches on what it means to start before you feel ready, reminding us that courage isn’t the absence of fear—it’s learning how to live alongside it.

See omnystudio.com/listener for privacy information.

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.

See omnystudio.com/listener for privacy information.

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.

See omnystudio.com/listener for privacy information.

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?

See omnystudio.com/listener for privacy information.

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.

See omnystudio.com/listener for privacy information.

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?

See omnystudio.com/listener for privacy information.

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.

See omnystudio.com/listener for privacy information.