The obvious gap between top-down planning and bottom-up research emerged as one of the main lessons from a two-year City Studio in the suburb Rosettenville within Johannesburg, South Africa. As a response, a pop-up board game called Streetwise Six turns into an active learning tool and pedagogic decolonisation device for different stakeholders. The game takes players on an imaginary walk along the city streets and allows them to explore multiple layers of the everyday, including non-formal processes with often invisible yet highly organised rules and regulations. The inherent storyline, character selection, building components and political scenarios are based on research and findings of the studio and actual events, to be explored in newly played out complicities. The chapter evaluates the potential of Streetwise Six as a form of knowledge production in an educational system that operates at the intersection of academia and local community engagement, in a postcolonial, post-apartheid context.