Occupational stress is associated with numerous health problems that cost organisations considerable resources. We explore whether the detrimental effects of stress on individual health are accompanied by productive effects on individual performance for self-employed people, thereby making stress somewhat “worth it” for this occupational group. Given that positive affect can serve as a stress-buffering resource, we also examine the potential for positive affect (PA) to moderate these relationships. Our hypotheses are tested using data from the NHANES I Epidemiologic Follow-up Study (NHEFS) that incorporated extensive demographic, medical history, nutritional, clinical, and laboratory data representative of the non-institutionalised civilian US population. From this dataset we created a longitudinal matched sample of 688 self-employed individuals and 688 employees, incorporating self-reported and physiological measures of stress and health. Our findings indicate that (controlling for past income and prior health) self-employed people experience greater stress than employees, and they experience a positive impact of stress on income despite a negative impact on physical health. These relationships are moderated by positive affectivity, where PA accentuates the positive effect of stress on personal income and mitigates the negative effect of stress on physical health.