Chronic stress has been associated with a range of health disparities, but examination of occupational stress, especially in the wake of COVID-19, has been minimal for many careers. A novel methodology involving work stress diaries and collection of salivary cortisol was employed to determine correlations between occupations, occupational stressors, and how well these are related to the physiological response to stress exposure, the release of cortisol. While cortisol levels tended to follow typical circadian rhythm based on sampling times, cortisol levels also followed the subjective stress levels listed in the work stress diaries following linear regression analysis using the pooled study population data (p = 0.042). When comparing the stressors between the studied careers, participants who worked in the healthcare industry accounted for one-third of the total participants, but reported nearly half (42%) of the more severe occupational stressors listed in the diaries. Finally, the most commonly listed emotional reactions to exposures listed included feelings of stress, frustration, anger, anxiety, or overwhelm. As the workplace progresses from the pandemic, the opportunity to reduce occupational stress exposures in the workplace is at hand. Companies that work towards minimizing the stress faced by their workforce would have a healthier and more relaxed workforce.