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Discussions about the decolonization of philosophy take place within the wider context of efforts to interrupt inherited hierarchies of knowledge and reimagine higher education as we know it. In this presentation I offer some insights from recent research and pedagogical experiments that engage the challenges and complexities of undertaking decolonizing work in a contemporary educational context characterized by volatility, uncertainty, complexity and ambiguity (VUCA). Rather than prescribe a single pathway forward, I invite people to develop the capacities and the stamina to walk toward as-yet-unimaginable futures with more honesty, humility, and hyper-self-reflexivity. In particular, drawing on my work with the Gesturing Towards Decolonial Futures research/arts collective, I will review a series of pedagogical frameworks that we have developed for inviting intellectually and relationally rigorous engagements with social and ecological challenges.