Although temporality is pivotal to most career development processes, qualitative longitudinal research (QLR) is still rare in vocational psychology. QLR consists of following individuals over the years and exploring how they develop through time. It implies articulating themes, cases, and processes to reach an understanding of change in the making. Based on two vignettes showing how the entourage influences career change processes, we address the heuristic, praxeological, and transformative potential of using QLR in vocational psychology and, more specifically, to study career transitions. This approach also raises practical and ethical challenges that must be considered.