Alarmed by the planetary crisis, Bernard Stiegler demands that a philosophy of education be reimagined to preserve knowledge and envisioned negentropic education as an essential response to the Anthropocene. This paper aims to chart a path for negentropic education in three ways. First, we examine the anxiety related to existential threats that shape life and learning in the metacrisis. We offer an existential approach to anxiety, drawing on Sartre’s ontology of human freedom, particularly his emphasis on resisting bad faith and nihilism as a critical step toward an authentic response, in the quest to reclaim our connection to others and the environment. Second, we turn to Dufourmantelle’s work on wise-risking and gentleness to develop teaching strategies for coping with anxiety. Her works offer ways to connect students emotionally and practically to the world-in-crisis. We then turn to Stiegler’s meta-analysis of how technology and capitalism are destroying teaching and learning, and his proposal for negentropic education as a way out of the metacrisis. Adopting Sartre’s and Dufourmantelle’s insights, we offer a brief sketch of some elements of a negentropic pedagogy, one that may facilitate the radical social transformation – what Stiegler calls bifurcation – that is necessary for post-anthropocenic education.