This article draws on the findings of an in-depth study which sought to explore the career histories and professional aspirations of 12 women deputy head teachers in England. In view of the ongoing underrepresentation of women in secondary headship and the scarcity of literature focusing solely on deputy heads, the study aimed to gain an insight into how female potential aspirants to headship perceive their professional futures. This article explores the heterogeneous ways in which the sample experienced deputy headship and the influence that these experiences had on their career aspirations. The themes that emerged from the women's narratives highlighted both the enabling and constraining nature of deputy headship. Analysis also revealed that deputies' day-to-day work had the potential to facilitate or curtail aspirations to headship. This article argues that women's experiences of deputy headship should be taken into consideration in debates concerning the underrepresentation of women in secondary headship. Implications for leadership development and support as well as avenues for future research are identified.