Sport provides many youth participants with a central life project, and yet very few eventually fulfill their athletic dreams, which may lead them to disengage from sport entirely. Many studies have explored the processes of athletic retirement, but little is known about how youth athletes actually reconstruct their relationship with sport and embodiment postretirement. The authors explored these issues in the story of “Pilvi,” a Finnish alpine skier who disengaged from sport in her late adolescence. Employing an existential-phenomenological approach, they conducted six low-structured interviews with Pilvi, combined with visual methods, and identified key themes relating to the body, space, culture, and time. Their findings highlight the difficulty of building a new relationship with sport and the often restrictive cultural horizons of sport and exercise culture that limit the “possible selves.” The authors discuss the significant implications for applied practitioners helping youth athletes and effectively supporting them in leaving their sport.