"If you have the chance to be the best in the world at something, even for the fourth time, you should probably take it." Caryn Davies, a 3x Olympic medalist, shares her extraordinary journey of ambition, resilience, and self-discovery in this unfiltered conversation. Caryn, who competed in three Olympic Games—Athens (2004), Beijing (2008), and London (2012)—amassed an impressive record: a silver medal in Athens and back-to-back gold medals in Beijing and London as part of the U.S. Women’s Eight. She reflects on her initial decision to retire after London, only to feel drawn back to rowing years later, inspired by her enduring love for the sport and the possibility of a fourth Olympic appearance in Tokyo. Her return, however, was anything but straightforward. She recounts the struggles of reintegrating with a younger team, battling a significant injury, and ultimately being cut from the Tokyo squad. Despite not making the final team, Caryn explains how she redefined success: "Even though I didn’t make it to the Olympic Games... I had won something more important than a gold medal: the respect and love of my teammates." In this conversation Caryn shares about her learnings from the most challenging moments, including the power of vulnerability, the importance of seeking feedback, and the delicate balance of intrinsic versus extrinsic motivation. She also offers unique insights into what it means to embody the Olympic ideals of excellence, respect, and joy in effort: "A true Olympian honors not just excellence but also friendship and respect, even amidst fierce competition." Caryn takes us behind the scenes of her life as an elite rower and shares how the lessons from her Olympic journey now guide her in her career as a lawyer. She shares how "being a normal person [not an elite athlete] is really hard." This conversation is a testament to the idea that greatness isn't just measured by medals but by the impact you leave on those around you.