The recent growth in self-employment has sparked scholarly interest in why individuals choose and remain in self-employment. Yet, relatively little is known about how self-employed workers enact their daily lives and what this means for their work–life interface. Self-employment is often presented as a means to enhance life choice and as enabling work and nonwork activities to be combined more satisfactorily. However, extant evidence on how self-employment is experienced is mixed, with some studies reporting long and irregular working hours and high levels of stress. Furthermore, the way in which self-employment is experienced may be influenced by national context – economic, institutional and cultural factors. In this paper, we develop a multi-level model which extends existing work on the Person–Environment Fit by incorporating factors relevant to self-employment. The model assists us to understand how contextual factors create both opportunities and tensions which impact the work–life interface of self-employed workers.