This study was designed to explore whether sport participation contributes to life skill development and if so how these skills aid professional success. The research questions were: 1) Which life skills were perceived by successful individuals to have contributed to career success? 2) What did they understand were the sources for these life skills? 3) What was the learning mechanism for these life skills? 4) How are life skills understood to have developed through sport, applied in professional work? This research offers empirical evidence that life skills perceived to have been learned through sport are strong contributors to professional success. The study employed case study methods and content analysis of data derived from fifteen in-depth semi-structured retrospective interviews with males having extensive but non-elite sport experience. Findings confirmed the development of life skills identified through prior research but also added constructs, particularly a special form of resilience, realistic optimism. Participants mentioned multiple learning sources for life skills, including education and family. However, sport experiences predominated. Handling pressure and resilience were learned primarily from sport; teamwork and confidence were learned solely from sport. The codes for learning mechanisms applied to this study were derived from social and experiential learning theories. The majority of learning instances were experiential, highlighting the importance of learning directly from experience and subsequent reflection. Life skills realistic optimism, confidence, and perseverance were learned primarily through experience; handling pressure and resilience were learned only through experience. This research adds to the literature by demonstrating within the experience of single individuals, evidence of direct transfer of skills from sport to work, and by identifying specific life skills perceived to aid career success. Findings provide practical insights for athletes, coaches, parents and educators and also suggest a number of topics for future research, including potential differences between men and women or competitors in individual versus team sports.