Purpose: In response to the Grand Challenge of promoting the Healthy Development for All Youth, many programs aim to enhance the development and transfer of life skills. However, within sport-based positive youth development (PYD) programs, life skills are understood through adult-centric perspectives. To better serve youth, research is needed that explores life skills through the lived experiences of youth. Method: Thirteen youth, who met the purposive sampling criteria, participated in the study. Data were collected using two methods. Semi-structured interviews explored life skill development, while photo-elicitation interviews explored life skill transfer. Results: Findings illustrated youth developed, as well as transferred, a variety of intrapersonal and interpersonal life skills. Youth identified, defined, and applied life skills that were both explicitly taught by the program and others that were not. Conclusions: Findings can be used to inform the strategic design of sport-based PYD programs and intentional facilitative coaching practices of their staff.