The main purpose of the exploratory research discussed in this paper was to generate insights into the complexity of the career-making processes involved in the transition from being a student to starting up a business. Using story-telling interviews, data were collected from fifteen graduates based in the Yorkshire region of the UK. Qualitative thematic analysis produced a chronological summary for each respondent, charting the sequence of events that led to start-up and providing appropriate context and rationale so that key themes could be identified. The research began as a study of the career-making process of moving from student status to self-employment; it ended by offering valuable insight into the complex transition process undertaken by a group of diverse graduates. This subtle shift of positioning is important, and reflects the outcomes of the in-depth research undertaken with the respondents. The findings suggest that only very rarely could the transition process be regarded as strategic. It was not a linear process with clear stages, but rather a continuous process which often stretched back to the respondent's pre-university life. The process is discussed in relation to three major themes: personal characteristics, employment experiences and lifestyle, and support. Appreciation and awareness of the lack of common transition and contextual processes, aspirations, factors and required capabilities must be reflected in policy and practice that seek to promote and enhance graduate entrepreneurship. The authors' findings question the suitability of neat policy formulas and skills-based interventions to encourage more students to take a start-up pathway. Further research is needed to strengthen the fledgling understanding of this process.