In this second interview with Dr. Sydney Ey, Professor of Psychiatry and Associate Director of the Resident and Faculty Wellness Program at the Oregon Health and Science University Medical School, she is joined by Dr. Stuart Slavin, ACGME Senior Scholar for Well-Being. In this interview, Dr. Slavin and Dr. Ey explore how imposter phenomenon manifests itself among residents and faculty, how it relates to perfectionism and depression, and discuss the multiple impacts impostor phenomenon has on their well-being. They also discuss the roots of impostor phenomenon and why it seems endemic to the experience of residency, sharing some of the strategies programs have used for combatting the hold it has over a person’s self-perceptions and the expectations they have of themselves.