This paper reflects on the challenges and possibilities of interdisciplinary, translocal efforts to create pedagogies that invite people to grapple with the foundations of global social and ecological injustice, and the difficulties of transforming them. It begins from a proposition that there is a ‘blind spot’ in analyses that uphold the sustainability of globalized capitalism and its interlocking systems of racialized and gendered oppression as a viable form of life. It considers how an ‘alternative thinking of alternatives’ is being practiced in learning spaces where future-making practices are being developed that recognize the harmful effects of this blind-spot. It emphasizes the importance of learning from both the successes and failures of these efforts. In particular, it identifies common circularities that emerge in alternative spaces that seek to transcend complicity in harm and gloss over the difficulties of transformative change. It describes how one collective approaches these difficulties by starting from acknowledging the irreducible complexity and complicity of efforts to ‘gesture’ toward future-making practice for viable ecological futures.