As more and more women choose to have careers and achieve manage­ment positions, research has examined how these women are faring in organizations (Kanter 1977), what their career choices have meant for their private lives (Marshall 1995, 1984), and the ways in which they manage (Rosener 1990; Shakeshaft 1987; Rosener 1990). The majority of these studies have documented the experiences of white women from developed countries such as the USA, Canada, Great Britain, and Australia. There are some studies which include African American women managers in the USA (Grogan 1996), and some which include Black and Asian women in Britain (Powney and Weiner 1991). However, the experience of women managers of colour from Africa, Asia, and the Caribbean is not well documented, and therefore it is not clear whether their experience is similar to or different from that of their counterparts in the developed world. It is likely that the different social contexts and cultural frameworks in which they operate make their experience qualitatively different. This paper documents the experience of a group of women secondary school principals who manage schools in a small Caribbean island state, Trinidad and Tobago. It shows that like their counterparts in the developed world, their personal and professional lives are closely intertwined, and that their race, class, and gendered positions impact on their career choice and promotional opportunities.