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Background: Impostor syndrome is an internalized sense of incompetence and not belonging. We examined associations between impostor syndrome and holding leadership positions in medicine., Study Design: A cross-sectional survey was distributed to US physicians from June 2021 to December 2021 through medical schools and professional organizations. Differences were tested with the chi-square test and t -test for categorical and continuous variables, respectively. Logistic regression was used to identify factors associated with holding leadership positions and experiencing impostor syndrome., Results: A total of 2,183 attending and retired physicians were included in the analytic cohort; 1,471 (67.4%) were in leadership roles and 712 (32.6%) were not. After adjustment, male physicians were more likely than women to hold leadership positions (odds ratio 1.4; 95% CI 1.16 to 1.69; p < 0.001). Non-US citizens (permanent resident or visa holder) were less likely to hold leadership positions than US citizens (odds ratio 0.3; 95% CI 0.16 to 0.55; p < 0.001). Having a leadership position was associated with lower odds of impostor syndrome (odds ratio 0.54; 95% CI 0.43 to 0.68; p < 0.001). Female surgeons were more likely to report impostor syndrome compared to male surgeons (90.0% vs 67.7%; p < 0.001), an association that persisted even when female surgeons held leadership roles. Similar trends were appreciated for female and male nonsurgeons. Impostor syndrome rates did not differ by race and ethnicity, including among those underrepresented in medicine, even after adjustment for gender and leadership role., Conclusions: Female physicians were more likely to experience impostor syndrome than men, regardless of specialty or leadership role. Although several identity-based gaps persist in leadership, impostor syndrome among racially minoritized groups may not be a significant contributor., (Copyright © 2023 by the American College of Surgeons. Published by Wolters Kluwer Health, Inc. All rights reserved.)