Sustainability is seen as the solution to the wicked crisis of our unsustainability. However, the ways in which we know, understand, and enact sustainable solutions can often mean our participation reinforces the systems, institutions, and paradigms which have created our unsustainable societies in the first place. So how can we learn to be, do, think differently within them? Guided by a post-qualitative approach, this project investigates the relationship between knowledge systems and sustainable transformations, in an attempt to understand how we “know” sustainability and how such knowledge affects our ability to enact it. By deconstructing this relationship and situating it within communities of practice and the socio-historical frames of capitalism and colonialism, one’s own role emerges as a learner, researcher, and participant in transformation. In this situatedness, the need for concurrent transformations becomes clear: of not just the political and economic systems that drive our constant growth, but also the knowledge systems which underpin them. In this light, the Open Knowledge movement and Braided Knowledges are used as two case studies of knowledge system transformation, which provide an early glimpse into how our relationships with knowledge may help lead the way towards sustainable futures.