The purpose of this narrative inquiry was to explore the lived experiences of college-educated, immigrant women from the Caribbean in their quest for professional advancement in educational leadership roles in the United States. There were six participants for this study who were selected based on convenience, purposeful, and criterion sampling. Each participant's lived experience was explored through a triangulation of information provided from two in-depth face-to-face interviews, document analyses, and observation/field notes. The findings indicate that Caribbean immigrant women studied navigated hills and valleys that included acculturative stress. Furthermore, the participants are characterized with a "militant motivation" in their approach to achieving their goals; thus having an attitude of "by any means necessary" was essential to their success. To accomplish their goals and successfully navigate the hills and valleys, the participants shared the support of strong matriarchs in their family and with the added help of the village; they also engaged in adult learning practices in their efforts to excel. Additionally, a Caribbean identity was utilized as a source of resistance and high self-esteem bordering on ethnocentrism against prejudices to facilitate the journey to success. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]