While the field of career psychology has shifted its attention to the study of career development, the developmental stage of childhood has often been neglected. Similarly, there is an absence of career research of a longitudinal nature, despite consistent calls to focus more on longitudinal methods when studying career development. The present study forms part of an existing longitudinal project which investigates the career development of South African children. This study, initiated in 1998, attempts to explore the occupational aspirations and gender stereotypes of a group of 39 children in the Nelson Mandela Metropole. The results from this study will provide much needed baseline information on how South African children become aware of careers, as well as provide useful suggestions on how to develop career education syllabi, particularly within the Life Orientation curriculum. The present study aims to explore and describe the changes that may occur in the participants’ occupational aspiration interest typology, status levels, and gender stereotypes over a five year period. Both developmental and career developmental theories were used to provide a theoretical context from which the participants’ career development could be explored. The study is quantitative in nature as it made use of semi-structured interviews and a biographical questionnaire in order to quantitatively transcribe the data. The questionnaire consisted of four broad questions which asked for information regarding the participants’ occupational aspirations, how much information the participants had about the chosen occupation, the number of occupations the participants knew about, and the extent to which the participants held gender stereotypes regarding fourteen different occupations. Descriptive statistics were used to describe the findings of the data which had been coded according to Holland’s typology of occupations. In addition, content analysis was performed to elicit themes regarding the participants’ own reflections on their career development. Results from the data analysis revealed that the majority of participants aspired to Social type occupations throughout the five years under study. Furthermore, most participants consistently aspired to high status occupations throughout the five years. Similar results were found for girls and boys. The results also demonstrated that the participants’ gender stereotypes tended to decrease over time, particularly as their occupational information increased. Lastly, most children were able to reflect on their career development and attributed changes in their occupational aspirations to changes in their interests. The results from this study offer insight into the development of occupational aspirations and perceptions of South African children which can be used as a foundation for future research and which should be valuable in the development of relevant career education programmes for South African schools.