This article demonstrates how qualitative research methods can contribute to theorising complex facets of entrepreneurship. Qualitative research has been attributed with producing some of the most interesting research in management (Suddaby, 2006). This study, of how observational learning influences the transition into entrepreneurship, builds on an emergent literature developing the concept of entrepreneurial learning. It adopts a life course method, an approach traditionally rooted in social psychology. Theoretically it builds on Bandura’s (1986) Social Cognitive Theory to develop insights into the social dimensions of learning prior to start-up.