Entrepreneurial activity leads to certain events that can impact both the equilibrium of a small business and that of its owner-manager. Although the health of the owner-manager is a key asset for a small organisation, the characteristics of the events he experiences and his psychological reaction to these episodes remain underexplored. This paper aims to address these research gaps, which are common to both occupational health and entrepreneurship, two fields that are rarely combined. We conducted a mixed methods study using a panel of 357 small business owners-managers. First, a qualitative longitudinal survey was administered to semantically categorise the most salient events experienced by the owners. Next, a quantitative, cross-sectional questionnaire was administered to weight the coded events through two mediating constructs: stress and satisfaction. Finally, we assessed the events' effects on the owners' health variances through linear regressions. Conceptually, our results extend the affective events theory to small business owners. Methodologically, we offer two checklists of events that capture emotional stress and satisfaction in entrepreneurial activity. Practically, certain preventive actions by medical professionals can build upon these checklists' predictive qualities regarding health. These checklists, referred to as a 'stressometer' and a 'satisfactometer', are also benchmarking tools for any self-employed.