Purpose: To support the healthy development of youth, programs have begun embracing the strength-based approach of positive youth development (PYD), with sport serving as a unique learning context. However, much remains unknown about the life skill transfer phenomenon. Methods: Using photo-elicitation methods, the current study sought to explore the transfer and application of life skills from the perspectives of 12 Black youth (ages 9–14 years old) who participated in a sport-based PYD program. Results: Findings from a document analysis illustrate the transfer of self-control, effort, teamwork, as well as personal and social responsibility. Further, findings identify specific transfer contexts (e.g., home, sport, school, community) and highlight how life skills are applied. Discussion: The study provides a unique snapshot into the lived experiences of youth, illustrating life skill transfer opportunities, as well as the potential for collaborative efforts with key adult figures throughout the developmental ecology of youth.