The making of career choice is seen as an important decision in an individual’s life. Research in South Africa suggests there is little yet growing empirical focus on the career development processes of individuals termed as ‘previously disadvantaged’ by the apartheid policy of racial separation. The goal of this study was to investigate the factors that influence distance learning students’ career choices among a sample of previously disadvantaged distance learners in South Africa. Data were collected from 40 participants using unstructured interviews. Upon analysis, five themes emerged as influencing career choice: the influence of (a) significant others, (b) academic performance, (c) personal circumstances, (d) environmental forces, and (e) career interventions. Furthermore, each of these factors influencing the making of career choice was accompanied by difficulty en route to the enactment of choice. Based on the findings of this study, career counsellors can come up with interventions targeted at previously disadvantaged individuals. This can not only help in empowering career counsellors to understand their clients but also help in understanding the career development processes of such clients.