Gaming literacy proposes specific ways of thinking and acting by providing cognitive, creative, and social skills, which are necessary in the face of complex (Zimmerman, 2008) and wicked problems we encounter in today’s society (Rittel & Webber, 1973). This paper presents preliminary findings from an exploratory study of how students within arts, design and media might redesign board games and develop gaming literacy; helping them understand and make sense of the world “from the point of view of gaming” (Zimmerman, 2008, p. 156). Through research-based teaching at both bachelor and master levels, we developed a work-in-progress workshop where students must face complexity and practice navigating it. In the workshop, students redesigned the familiar board game Monopoly, using it as a metaphor, and our emergent findings suggest that it can provide a scaffold that enables students to map, prototype and simulate different complex problems and systems onto it - without prior game design knowledge. Monopoly introduced a balance between familiar and known rules and constraints on one side, and hackability and the freedom of play on the other. The monopoly workshop provides an experimental, hands-on, and collaborative approach to understanding complexity through intertwined actions of exploring, prototyping, testing, and reflecting (Zimmerman, Forlizzi & Everson, 2007). We found that the success of such a process seemingly depends on the facilitator and the participants. Here, allocating time for explicit reflection on learning outcomes was a necessary and vital part of the workshop (Alme & Hvidsten, 2022; Dewey, 2018). This work-in-progress workshop method contributes to studies of pedagogical games by focusing on how students might develop gaming literacy through board game redesign, offering a novel, hands-on model for engaging students in, and understanding, systemic complexity. We suggest that future research should validate this approach further, in other contexts and with other types of (board) games. Further, future research should investigate this approach as an introduction to the overarching model of gaming literacy in the face of complex problems.