M.Ed. / The influence of the HIV/AIDS pandemic as well as the significant impact it has left on children and adolescent who are left without parental guidance and support has huge implications for communities. As the epidemic spreads, adolescent-headed families are becoming more and more frequent in society, posing great challenges to extended families that have to care for additional children, causing a collapse on parental functions. This leads to the emergence of a new family structure where great strain is placed on children who are often left to fend for themselves. The absence of parental care and support often not only affect their social emotional development, but also their scholastic performance. This inquiry attempted to understand how these adolescents cope with difficulties related to living without caregivers, and as to how some can overcome the odds and still successfully progress with expectations placed by the school context. The inquiry utilized a phenomenological research design that is exploratory in nature. The data collection methods included semi-structured interviews with four participants, two boys and two girls. Each of the four participants also wrote narratives of their life stories. Two focus group interviews were also conducted, one with the four participant's educators and the other with another group of adolescents from adolescent-headed families. Data obtained was analysed using content analysis to determine the common themes and subthemes that emerged.