In recent years, entrepreneurship has grown as an attractive career alternative, promoting much scholarly attention. Still, little is known about the work–life interface of entrepreneurs, in particular whether entrepreneurship enhances work–life balance or exacerbates conflict between domains. We base this study on boundary theory to explore how subjective perceptions of balance and boundary management might illuminate this contradiction. Indeed, entrepreneurial roles are unique in that they entail high flexibility and permeability, facilitating role blurring, or boundarylessness. We interpretively explored three research questions pertaining to entrepreneurs’ perceptions of their work–life interface and boundaries between roles, as well as the context factors that could explain these perceptions. Findings suggest that several subjective as well as objective factors could explain how entrepreneurial work is sometimes experienced as conflicting, and at other times, perceived as conducive to balance. Theoretical and practical implications and recommendations as well as study limitations are discussed in closing.