According to a popular adage, when the going gets tough, the tough gets going. With unemployment on the constant increase in South Africa, people are becoming more relentless in seeking means to earn a living. Waste picking has become, for example, an option for individuals in responding to the economic challenge in order to provide for themselves and families. By odd, the researchers refer to foraging in bins for items that have been discarded by others, which may be sold for cash. Although this practice offers an opportunity for self-employment, there is also a concern that those who deal in waste may be exposing themselves and perhaps their families to social stigma and health problems. This article looks at both the challenges of waste picking (more specifically health) and the desperate state of unemployment in South Africa. In doing that, we aim to address three central questions: (1) why are people waste picking? (2) Is waste picking a sustainable venture? and (3) what are the challenges in waste picking? To obtain deeper insights into the themes captured in the aforementioned research questions; face to face interviews were conducted with participants. Empirically, four central factors push participants into waste picking ventures: unemployment, retrenchment, unemployability, and the need for augmented income. Also, we found that although waste pickers continue the practice to sustain themselves and their families, waste picking does not sufficiently offer sustainable income, improved livelihoods nor reduced dependency on public social and health systems. There is a need to enhance the capacity of the South African public health system to adequately cater for those who regularly need its services and as this study has shown, the continuous practice of waste picking is synonymous with ill health and pressure on public health systems. We flag directions for future research.