Coach developers play essential roles in “coaching the coaches,” and investigating their lifelong learning pathway is key for better understanding the mechanisms that lead certain coaches to become coach developers. Thus, the purpose of the paper was to conduct a case study to investigate the lifelong learning pathway of a coach developer operating in a national sport federation. The case investigated is Mille, a certified coach developer in charge of the Brazilian Rugby Federation’s coach education program. Data were collected through the Rappaport Time Line and two semi-structured interviews. An interpretative phenomenological analysis was adopted to explore the lived experiences reported by the participant. The results highlighted that Mille is an individual driven by challenges provided either by external factors (i.e. school, university, work) or by his own choices (i.e. becoming a coach, becoming a coach developer, starting a PhD) for personal and professional development. Specific life events led him to make decisions for evolving in his roles, from athlete, to coach, to coach developer, and to “master trainer,” which is the highest level of certification provided by World Rugby. Practical implications are suggested to contribute to the organization of education initiatives for coach developers through a lifelong learning perspective.