Introduction Burnout is common among clinical specialties and has implications on the residents’ well-being and mental health. Evidence suggests that optimism and burnout are correlated, but research has not focused on the applicability to medical residents. The objective of the study was to define burnout in residents and correlate it with optimism. Methods The authors conducted a correlational, prospective cross-sectional study using self-reported single item burnout (1-10) and Life Oriented Test-Revised (LOT-R) (0-24) survey instruments among residents of neurosurgery, neurology, internal medicine, family medicine and emergency medicine at a community-based hospital. Residents were asked to fill out the survey once in the 2018 academic year and once again in the 2019 academic year. Burnout and optimism scores were correlated and compared across subgroups for each year. Results There was no statistical significance found amongst any subgroups in burnout in 2018 but significance was found for both internal medicine (t = 3.74, p = 0.001) and neurosurgery (t = -3.07, p = 0.01) in 2019. Mean burnout increased from 2018 to 2019 from 4.39 to 5.1. Optimism remained constant from 2018 to 2019 (16.7 and 16.76, respectively) and there was no difference across subgroups. There was a statistically significant negative correlation between burnout and optimism in both 2018 (r = -0.364, p = 0.006) and 2019 (r = -0.39, p = .001). Conclusion Burnout and optimism are negatively correlated. Although burnout increased over time, optimism remained constant indicating the stability of this trait and implication for future interventions.