We explore the dynamics of entrepreneurial performance and well-being through computational theory. Our model connects mechanisms of work-related motivation and strain processes with the unfolding of an entrepreneurial process. The simulation results show that how an entrepreneur’s energy ebbs and flows over their journey, charting certain venturing performance and levels of well-being, can be linked to distinct interplays of ambition, skill, self-regulation, and dynamism. Our work contributes a holistic account of entrepreneurship and well-being, stimulates computational modelling, and enriches discussions about the entrepreneurial future of work.