Through the use of the framework of risk and resilience in a narrative inquiry, the present study examined the protective factors affecting the academic success of 24 Jamaican women in a graduate cohort in educational administration. All but two of the women rose from poverty to become academically successful, defined as having achieved graduate student status in educational administration. The protective factors found in the women can be grouped under three broad categories: strong personal identity traits, such as perseverance and a sense of faith; positive relationships that served as sources of support; and the ability to reframe barriers to success. In view of the obstacles they faced, it took multiple protective factors working together to overcome the risk factors that the women encountered in their paths to academic success. This article further includes discussion about the cultural patterns relevant to Jamaica that contribute to both the risk and protective factors of women.