In this paper, we aim to unveil the complexity and dynamics of entrepreneurial stress by analysing accounts made by entrepreneurs who have experienced severe stress. We recognize stress as a complex multiyear phenomenon, the intricacies of which cannot be adequately captured through quantitative analysis of the relationships between individual variables. To this end, we apply narrative analysis to gain a deeper insight into the phenomenon of entrepreneurial stress. Our findings reveal the complex nature of stress and illuminate how entrepreneurs’ beliefs and characteristics, such as optimism and self-efficacy can expose entrepreneurs to increased stress. The results of the paper contribute to the literature on entrepreneurial stress and well-being.