Although the wide-scale disruption precipitated by the COVID-19 pandemic has somewhat subsided, there are many questions about the implications of such disruptions for the road ahead. This year’s Research in Medical Education (RIME) supplement may provide a window of insight. Now, more than ever, researchers are poised to question long-held assumptions while re-imagining long-established legacies. Themes regarding the boundaries of professional identity, approaches to difficult conversations, challenges of power and hierarchy, intricacies of selection processes, and complexities of learning climates appear to be the most salient and critical to understand. In this commentary, the authors utilize the relationship between legacies and assumptions as a framework to gain a deeper understanding about the past, present, and future of RIME.