The sustainability imperative requires that we REDO the products, systems and paradigms we are part of, think and do. Yet, entangled habit and fear can stop us from engaging in profound processes of change. In this talk, I want to creatively critically explore the man-madeness of the systems we live by, and design’s agile dance with them. I will draw on experiences from education, research and play to discuss both the promise and responsibility of freeing design.