High-performance sport impacts athletes beyond the physical. Coaches and coaching practice are particularly influential in shaping this learning and development. This article examines the learning identified through an inductive content analysis of eight former Olympic athletes’ career narratives. Three phases of learning could be identified across the cohort: ‘Growing into high-performance sport’, ‘Making sense of high-performance sport’, and ‘(Re)shaping high-performance sport’. A cultural perspective of learning, in particular the metaphor of ‘becoming’, is employed to interpret the Olympians’ learning experiences. The findings of this research indicate that athlete learning is bound by particular high-performance sporting contexts and career phases, yet impacted by the athletes’ individual backgrounds and dispositions. Further, data indicate that athletes’ personal development reflexively intertwines with athletic performance and performance enhancement. Implications for coaches are to: (1) involve athletes in co-constructing their sporting cultures and training contexts; and (2) provide possibilities and support for athletes to develop personally.