In educational leadership there appears to be a disproportionately low number of female head teachers in comparison to the number in teaching. This article explores whether embedded links between leadership and masculinity still exist, and reports on the reasons given by a sample of three male leaders as to why they pursued careers in educational leadership. Existing research into headship is investigated and whether the gendered construction of leaders and leadership was considered and contributed to the choices made. By interviewing head teachers I explore views on the perceived advantages and disadvantages that males and females face in their rise to the top role. The head teachers deem the underrepresentation to be resolving itself as increasing numbers of females in leadership teams should automatically lead to increased numbers of female heads. They feel content to retire from the profession safe in this knowledge.