This research report builds on the work already completed in the field of women in school leadership. Although a number of studies have examined female principals at work in primary schools in rural areas, there has not been a strong focus on female principals at work in secondary schools, in urban areas. The underrepresentation of women in school leadership is not unique to South Africa. It is a global phenomenon, which can be traced back to the patriarchal values, which exist in most societies. The purpose of my research report is to investigate how the capabilities approach can inform our understanding of women progressing into leadership positions at secondary schools in South Africa. A qualitative method was used based on an interpretivist research paradigm. The research design was a narrative inquiry. A purposive sampling method was used and data was collected by means of semi-structured interviews. The drive and determination to “make a difference” and “be a role model” enabled all five participants to convert their capability set into functionings thus “shattering the glass ceiling”.