The number of children being abandoned in South Africa is rising steeply. With already existing challenges in the current South African labour market, one must consider the expectations of abandoned adolescents in terms of future careers. It is unreasonable to expect an abandoned adolescent to be guided towards making career decisions using modern career counselling methods, as these were developed for use with individuals from traditional, nuclear families. Most abandoned adolescents are taken in by extended family; grow up in children’s homes or on the streets. One can expect these circumstances to negatively impact the abandoned adolescent’s outlook and hope for the future. There is thus a need for an approach to career facilitation, which takes into account the abandoned adolescent’s subjective experience of his/her context. It was the primary goal of this study to investigate the possibility and limits of life design counselling with an abandoned adolescent. This was done against the background of both the systems theory and social constructionism in order to help the researcher to focus on the experience of the participant within his/her unique context. The study specifically focused on the experience of an abandoned adolescent. In order to better understand the subjective and diverse experiences of the participant, I aimed to investigate, through the lens of social constructionism, the way in which abandoned adolescents in general (and my participant in particular) create meaning through interaction with others as well as his/her environment. Within the qualitative paradigm this study was conducted by means of a case study during which a variety of postmodern techniques were implemented in order to facilitate co-constructive conversations with the participant.