What does it take to become the most decorated U.S. Cross-Country ski racer of all time? For four-time Olympic medalist, 33-time World Cup winner, four-time Overall World Cup Champion, and seven-time World Championship medalist Jessie Diggins, it’s about more than medals—it’s about resilience, vulnerability, and the unbreakable bonds of team. Fresh off her retirement, four-time Olympic medalist Jessie sits down with Mikaela to share the real stories behind the sparkle, the pain cave, and what's next.
Jessie and Mikaela dive into Jessie’s Minnesota roots, the team-first culture that shaped her, and the mental strategies she’s developed to thrive in the infamous dance with the “pain cave” (as Jessie says, a "pain cave waltz"). Jessie shares candid stories about setbacks, resilience, and the importance of defining success by your own values—not just results. The conversation also explores Jessie’s advocacy for mental health, climate action, and youth access to snow sports, including her work with Share Winter Foundation, Protect Our Winters, and the Emily Program. Jessie opens up about her documentary “Threshold"—Executive produced by Patrick Dempsey—why vulnerability matters, and how she found peace in retirement by focusing on purpose beyond medals.
Whether you’re an athlete or just looking for inspiration, this episode is packed with wisdom, honesty, and a whole lot of sparkle.
Presented by STIFEL...
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More about Jessie: https://www.instagram.com/jessiediggins/