In light of feminist scholars who have called for challenging the epistemology of existing theories and concepts in social sciences and recreating an innovative knowledge in which women are the focus, the current study aimed at tracing the career stories of 25 Israeli female deputy heads who explicitly do not aspire to headship. These deputies hold a stance that is in sharp contrast with widespread beliefs on career aspiration and advancement, albeit that they are considered to be competent candidates for headship. The female deputies' stories revealed that they construct a clear and sharp distinction between the deputy's role and that of the school head. Whereas the former is perceived to be challenging and less complicated, leaving them sufficient space to establish informal, warm relationships with staff and students, the latter is portrayed as stressful, formal and essentially administrative-oriented. This distinction corroborates the dichotomy of masculine versus feminine leadership, and provides insight into new conceptions of headship and deputy headship in the era of marketization and accountability. Practical and empirical implications are suggested. (Contains 1 note.)