Based on cognitive-behavioral and self-determination theories, this study examined differences in work-related well-being between managers and employees, focusing on perceived stress, life satisfaction, health, and income. It also explored the role of physical activity (PA) and its social support. Structural equation modeling supported the development of a well-being index. The sample included 446 employees and 110 managers, with a female majority (75.7%). Participants completed several demographic questions and two validated psychometric questionnaires, the Satisfaction with Life Scale and the Perceived Stress Scale, on the Qualtrics research platform. A multivariate analysis of covariance, controlling for age, PA, work environment, and education level, found that managers reported higher perceived income and life satisfaction than employees. However, the variance explained was under 4.0%. No significant interaction was found between gender and job position; however, women in both groups reported lower incomes than men. PA and its social support were positively correlated with life satisfaction and negatively correlated with stress. Childhood PA was linked to current PA, aligning with previous research. These findings suggest that the anecdotal well-being gap between managers and employees is far smaller when key influencing factors are controlled. The cross-cultural and gender-balanced reliability of these findings should be further evaluated.