There is a concern that South African youth growing up in underprivileged communities will internalize and replicate violent lessons from the past. When exposure to criminal activities and violent conducts becomes an everyday occurrence both in the community and in schools, positive youth development becomes challenged. Education is regarded as a fundamental building block in the society and provides youth with opportunities for the future which their parents never had during the apartheid years. Education in South Africa is considered as a key tool to promote positive youth development to benefit the individual as well as the society. Though the country has managed to achieve universal education, access to quality education remains an issue. Quality education is associated with a child-centred approach to teaching where one of the goals is to promote gainful and meaningful learning outcomes to prepare children for the future world of work. Inequalities in South African schools still exist and the majority of South African pupils attend schools with inadequate resources to fully meet their needs. School is pointed out as an arena where positive youth development can be promoted by focusing on development of the individuals’ full potential. It is also identified as an important location for intervention and a place where teachers as well as pupils can work together in promoting positive, democratic values.This study set out to examine the everyday lives of teenage boys in two of Cape Town’s township communities. The study seeks to explore what challenges male youth recognize in their neighbourhoods and the role of school in responding to them.By looking at a Waldorf school and a public school, representing two different approaches to teaching, the study seeks to examine how teaching can help youth respond to the challenges they face. The Waldorf school represents a humanistic child-centred approach to teaching and the study set out to examine whether or not this school, compared to a public school, differed in their views and strategies in responding to their pupil’s needs.The findings suggest similar community challenges between the boys in the two schools. The main challenge pointed out among the boys was the issue of gangs which they associated with fear, threat, the likelihood of doing drugs, and group pressure. The boys reported being bullied as well as the risk of getting killed if they said no to gangs, and identified limited opportunities to stay safe. School and homes was acknowledged as safe venues, but moving around within the neighbourhood often required support and protection of a gang or a group. The teachers who participated in this study were asked about their vision of school and how they thought school could respond to the challenges faced by teenagers. The teachers differed in their responses; those from the public school focused on collaboration with other stakeholders in the community when solving issues related to gangs and violence, while the Waldorf teachers emphasized their approach to teaching itself as a strategy to help the pupils. The Waldorf teachers emphasized humanistic values and the importance of fulfilling the pupil’s needs by responding to them as central points in their teaching. All the boys participating in the study enjoyed school and the opportunities it could provide. They all acknowledged the importance of education and showed awareness of what opportunities it might bring. The boys showed no lack of ambitions and saw their future roles as beneficial to their community. Though all the boys appreciated school, the boys in the public school reported being beaten by their teachers. This suggests that even though corporal punishment is prohibited in South Africa, it remains a daily experience for some pupils. It can be argued that corporal punishment in school contributes to the normalization of violence in youth’s environment. If teachers – pointed out as role models and transmitters of knowledge and values – contribute to this normalization, it is important to ask what values exists within their teaching. The aim of this study is not to explore whether or not corporal punishment contributes to a culture of violence; rather, it looks at what kind of values and vision are represented in two different schools and how they can have an influence on youth when it comes to dealing with the challenges they face.