South Africa has been going through severe social changes over the past two decades. In light of these changes the present study aimed to understand adolescents’ expectations of their personal future. Based on the Theory of Possible Selves (Markus & Nurius, 1986) the present research addressed the overall question whether adolescents’ personal future plans incorporate the views they share about the present and the future of their social context. Social context was not only limited to factors such as gender, ethnicity and school environment, but also included both the daily lived experiences of inequality, as is the case in South Africa, and the projected social context of the future. A total of 631 pupils from four Gauteng high schools took part in this cross sectional study. The results support the hypotheses especially within the possible selves’ domain of academic achievement. The interrelatedness between possible selves and shared beliefs about the future of South Africa could, however, not be demonstrated.