Extensive information exists regarding the university choice process for some students, but little is known about the process for students who do not move directly from high school diploma to higher education. In this article, we explore the process that these nontraditional students take to earning a university education. In-depth semi-structured interviews were conducted with eleven students attending classes at the University of the West Indies, Mona campus in Jamaica and the Cave Hill campus in Barbados. These participants decided to pursue higher education but did not have the resources to attend university immediately following high school graduation. We focused on these students’ educational and professional experiences and the ways those experiences influenced baccalaureate aspirations. Some findings from the analysis included: being classroom teachers was a major route; family support was a driving factor for students to reenter and strive to get a university education; and there were major financial struggles once students engaged in university study.