Purpose ‐ The purpose of this paper is to analyse how the transition into entrepreneurship is constructed in the context of the boundaryless career. The paper focuses on a particular type of career transition driven by dismissal or unemployment. Design/methodology/approach ‐ The research material is collected in life-story interviews with three Finnish female owner-managers. In the study, a narrative analysis of the career move into entrepreneurship is conducted. Findings ‐ The results demonstrate how the concept of the boundaryless career and career discourse as such, and the personal career history and the larger employment setting in particular, are applied in making sense of the transition into entrepreneurship. The significance of dismissal or unemployment is not uniform, but is dependent on the participant's interpretation of the boundaryless career and work-based security. Entrepreneurship is constructed both as a gender-neutral and gendered process. Research limitations/implications ‐ The career perspective could be more widely applicable to research into entrepreneurship, and perceiving entrepreneurship as work could offer an interesting avenue for future interdisciplinary study within career research. Practical implications ‐ By portraying the transition from unemployment/redundancy into entrepreneurship as a normal career shift, entrepreneurship is potentially made accessible to a broader group of people including unemployed women. Narratives have potential to be applied as career management tools. Originality/value ‐ The paper provides a contextualised view of the transition into entrepreneurship after unemployment and demonstrates how the entrepreneurship process is connected to the individual work history, employment setting, and gender.