Despite the many clerkship models of medical education, all can be considered a form of experiential learning. Experiential learning is a complex pedagogical approach involving the development of cognitive skills in an environment with a unique culture with multiple stakeholders, which may impact learner motivation, confidence, and other noncognitive drivers of success. Students may delay the transition to the clerkship year for myriad reasons, and the intricate nature of experiential learning suggested this may impact student performance. This retrospective, observational study investigated the impact of clerkship postponement by measuring subsequent clerkship performance. Pre-clerkship and third-year clerkship performance were analyzed for three cohorts of students (classes of 2018, 2019, and 2020, N = 274) where students had the option to delay the start of their clerkship year. A mixed analysis of variance (ANOVA) and paired t-tests were conducted to compare academic performance over time among students who did and did not delay. Across three cohorts of students, 12% delayed the start of the clerkship year (N = 33). Regardless of prior academic performance, these students experienced a significant reduction in clerkship grades compared to their non-delaying peers. Delaying the start of the clerkship year may have negative durable effects on future academic performance. This information should be kept in mind for student advisement.