As a result of the AIDS pandemic, adolescent-headed families are becoming a common trend in South Africa. However, little is known about the experiences of the adolescent, especially within the school context. Hence the purpose of this article was to explore the experiences of adolescents within the school context. During our initial review of literature we became very disillusioned by the findings of previous studies that portrayed an extremely bleak picture of the experiences of such adolescents. We decided to focus on adolescents from adolescent-headed homes that were displaying resilience in their academic and personal lives despite the odds. Resilience theory and positive psychology assisted us in exploring this topic. Data were collected through individual and focus group interviews with learners and educators. The findings identify specific aspects that are essential to creating resilience to such an extent that they could be positive despite their life situations. We focus on those aspects to assist those adolescents that are indeed not coping.