Positive developmental outcomes for youth are likely to occur when adults intentionally design environments to facilitate that development. However, in sport, studies typically examine only one adult relationship at a time, as opposed to the many that exist. The purpose of this study was to examine high school student-athletes’ perceptions of how a variety of stakeholders in their sport-ecosystem contribute to their life skills development and well-being. Bronfenbrenner’s Bio-Ecological Model and Prilleltensky’s concept of psychopolitical validity served as a guiding framework for interviews conducted with student-athletes (N = 46) in three different states in the United States of America. Themes suggested that the student-athletes’ relationships have a reciprocal interaction with their developmental experiences to create three different forms of development. Student-athletes had basic life skills recognition when learning without meaning was fostered by low-engagement relationships, development through adverse experiences when learning through necessity occurred through challenging relationships, and meaningful development when anchored learning experiences were supported by transformative relationships in their sport world. Lay summary: High school student-athletes were asked about their life skills development and how adults in their sport system influenced or hindered that development. Student-athletes favored highly engaged adults that supported opportunities by anchoring their learning in meaningful experiences. The relationship with the adult and the meaningful experience reciprocally influenced each other. IMPLICATIONS FOR PRACTICE Coaches, parents, and athletic directors should aim to provide opportunities for athletes to practice life skills in a meaningful way. Fostering positive relationships with student-athletes and being highly engaged in their development is favored by student-athletes. Transformative relationships and meaningful learning experiences may promote a better sense of community well-being.