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Abstract Background Medical students in the United States undergo three significant transitions as they progress from pre-clinical to clinical rotations, to acting interns, and ultimately to first-year resident. However, there is limited understanding of whether the factors and strategies that impact these transitions remain consistent or are unique to each individual transition. Methods Qualitative data was collected from three Nominal Group Technique (NGT) sessions held separately for third-year students (M3), fourth-year students (M4), and first-year residents (PGY-1). The participants were asked to share their perceptions on their most recent medical school transition. These responses were independently coded into thematic categories. Results The NGT session with M3 students (n = 9) identified 67 transition factors and 64 coping strategies. The M4 (n = 8) session identified 33 transition factors and 72 strategies to manage their transition. The PGY-1 (n = 5) session identified 28 factors and 25 strategies. The coping strategies for each session were categorized into seven themes and the transition factors were assigned to ten thematic categories. Conclusion Just as each transition is unique, so too are the number and variety of factors and strategies to manage each transition. Despite these differences, the themes of “Professional socialization” and “Prioritization, efficiency, and delegation” emerged as impactful in all three transitions.