The road to international sporting success is paved with difficult transitions. The present study is a qualitative in-depth interview study with 16 athletes. We first asked eight elite level athletes to provide a biographical description of their career path. We then asked eight young talented athletes to imagine they were at the end of a successful career and invited them to portray their imagined path. The elite athletes portrayed their career path as full of challenging transitions and existential concerns, and readily emphasized a number of internal and external resources as prerequisites for their successful careers. The young athletes portrayed an easy path with few hardships and emphasized internal resources over external ones. The study sets as a question for future research whether young athletes’ naïve and pervasive optimism is a cause for concern or an important internal resource for their further career development.