The document explores the factors influencing the career transitions of professional football players, particularly their shift to entrepreneurship or employment after retirement. Using a longitudinal data set from Portugal (1991–2017), the study finds that prior entrepreneurial experience is a key driver for retired athletes to pursue entrepreneurship, while those who worked alongside their sports careers are more likely to transition into employment. Interestingly, higher education levels did not significantly influence career choices, but having secondary education increased the likelihood of becoming an entrepreneur. The research suggests that engaging in work or entrepreneurship during the final year of an athletic career can improve career transition quality. The study highlights the need to expand dual career concepts beyond education and work to include entrepreneurship, emphasizing the importance of proactive career planning for athletes.