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This paper considers the distinction between ‘education’ and ‘schooling’ through the analysis of two main texts: Leo Tolstoy’s The Death of Ivan Ilych and Ivan Illich’s Deschooling Society. We aim to make some philosophical connections between the two texts as a way of critiquing capitalist institutional life while offering insights about how modern humans should learn, live, and die. In the first half of the paper, we suggest that dying and death provide opportunities to imagine ways we can teach, learn, and dwell more freely with others. In the second half, we focus on the creative capacities of human beings and how these capacities are threatened by the capitalist market, for which school serves as the primary advertising agency.