In this exploratory study, I analyse women’s experiences in a pre-professional business leadership setting. I adopt a perspective of structural contraints and conceptually draw on the construction of the ‘ideal’ female subject in late modernity and ‘new’ femininities. I argue that, although they are shifting, femininities persist to be a structurally rooted burden for assuming leadership roles for the women in this study. I develop my argument based on four interviews with women from an entrepreneurship programme in the United Kingdom. These women experience a double-bind in being a woman and being a leader and, importantly, anticipate further experience of such double-bind in the future. This creates a tension between their constructions of self, in which the women draw on ‘post-feminist’ discourses, and their experiences of inequalities. This research, hence, improves our understanding of women’s experiences in busines leadership settings by looking at the early-career stage, a perspective which is currently underdeveloped in the literature. This research also links women’s experiences in business leadership settings to the construction of the ‘ideal’ female subject and ‘new’ femininities by drawing on empirical data. The essay builds a starting point for further research by providing initial insights into these topics.