This paper presents findings from a study examining the career development experiences of female head-teachers in the south of England. Adapting a three-stage career model, the study examined different stages of the women's lives and careers in order to understand what encouraged and influenced them to become educational leaders and how their experiences shaped their perceptions of headship. The study used semi-structured life story interviews to generate rich accounts of women's lives from childhood. Findings suggest that parents exerted significant influence on the participants' values and ambitions, while teachers influenced their career choices. Their perceptions of headship developed and changed over time, transforming from feelings of shock at the reality and the complexity of headship to control and confidence that increased over first, second and third headships.