This article analyses interview data from 54 women school principals in South Africa to explore how women position their identities in relation to their gender, ethnicity and other characteristics. While grounded in their own context, the women's strategies resonate with those of women in many parts of the world. Five strategies are discerned: transforming the value of low-status identities, asserting a valued identity, negating stigmatised characteristics, denying disadvantage, and accepting women's inferiority. It is suggested that each may bring benefit to the individual but may also further embed disadvantage: that women are caught in a web of discrimination. It is argued that we do not sufficiently understand the complexity and balance of positive and negative effects of individual positioning on principals' lives and on wider structural change. The impact of action may not be captured by simplistic cause and effect analysis but appears to be both embedding sexism further and leveraging limited gains.