This paper generates insight into the social processes of observational learning and how these relate to entrepreneurship. Building on established theoretical frameworks of observational learning, it goes beyond the link between role models, self-efficacy and entrepreneurial intentions to understand how entrepreneurial models are observed within their original social settings. Empirically, it employs a life course qualitative research methodology to collect and interpret observations articulated as relating to the entrepreneurial journey. We extend previous studies by demonstrating how other people part of the same setting and timing of the observation influence the acquisition of entrepreneurial practices through observation.