The primary purpose of this case study was to develop, implement, and evaluate a new workshop-based intervention using the five-step career planning and reflect on feedback from participants (n = 17) with the aim of improving the intervention’s content and structure to apply it to a wider population of higher education students, including student athletes. The workshop-based intervention aimed to provide participants with opportunities to reflect on career planning and mapping while reviewing their past, present, and future in terms of both sports careers and life, generally. We provide our reflections for both applied researchers and practitioners on our experience of piloting the intervention. Semistructured interview data were collected from the participants. Analysis revealed that the workshop afforded participants with opportunities to reflect on their present and future careers. The participants also provided recommendations on how to improve future workshops. Reflections on these recommendations and on the workshop (development, implementation, and evaluation) are provided.