Comprehending praxis is a critical step in developing interventions that can have a real-world impact on people's lives. In this paper, we reflect on the lessons learned in the development of a curriculum for young people living in informal settlements in eThekwini, who are exposed to numerous vulnerabilities, including HIV-related risks associated with precarious urban livelihoods. Behavioural interventions have not led to commensurate reductions in HIV incidence, and the impact of these approaches remains regulated by numerous contextual conditions affecting those participating. Our collaborative project tested the impact of implementing a combination of the well-tested gender transformation intervention, Stepping Stones, with a new livelihood transformation curriculum, Creating Futures, among young people in eThekwini's informal settlements. Creating Futures was grounded in the theory and practice of sustainable livelihoods, but equally in the experience of the multi-disciplinary project team members who have conducted both research and development work among youth in the eThekwini area. Our approach was founded on the work of Doug Kirby, and we are indebted to him for his inputs. His logical model approach ensured that the team remained orientated to specific curriculum outcomes. Analysis of the results at 12 months post-baseline indicates positive livelihood outcomes.