Burnout is increasingly common in the medical field. In dermatology, burnout is attributed to high patient volume and excessive time spent on electronic medical record system activities. The shortage of the dermatology workforce in academic medicine is well-known. Studies have yet to examine the relationship between well-being during dermatology residency and the pursuit of academia. Objective: To assess the well-being of dermatology residents in the United States, identify barriers/enablers to well-being, and determine the implications of these measures. Methods: A cross-sectional survey was distributed to program coordinators of 136 accredited dermatology programs with instructions to forward to their current dermatology residents. Residents provided self-reported ratings on validated scales measuring burnout, depression, anxiety, fatigue, and quality of life. Descriptive statistics and correlations were examined. Results: Residents with higher levels of burnout reported they were significantly less likely to pursue academia, full-time work, clinical research, and fellowships after residency. The results showed opposite effects for residents with higher qualities of life. Conclusions: This study showed that resident well-being can have a significant impact on residents' future career plans, including pursuing academic dermatology, clinical research, and fellowship. Addressing burnout in the field of dermatology offers an opportunity to increase the academic dermatology workforce.