Existing research has primarily focused on the impact of entrepreneurial fear of failure on the entrepreneurial process, while largely neglecting its effects on entrepreneurs’ well-being. Drawing from conservation of resource theory, our study investigates the dual impact of entrepreneurial fear of failure on entrepreneurial well-being, proposing that entrepreneurial well-being is affected in opposite directions through two types of work-related rumination: problem-solving pondering and affective rumination. We also examine the moderating effect of emotion regulation. Using data collected from three rounds of questionnaire surveys among entrepreneurs in China, we employed a cross-lagged panel model for analysis. The results support our dual-path mediation model, with only cognitive reappraisal serving as a moderator. We contribute to the literature on entrepreneurial fear of failure and well-being.