In this essay, Ross Collin offers ethics-focused readings of Anton Chekhov's popular short stories "The Schoolmistress" and "The Teacher of Literature." Chekhov shows in the two stories how teaching can inhibit teachers' flourishing. That is to say, teaching under bad conditions can draw teachers into moral "catastrophe," to use Cornel West's term for an idea central to Chekhov's work. In "The Schoolmistress" and "The Teacher of Literature," Chekhov compares the catastrophes of teachers' lives to the catastrophes of the lives of nonhuman animals trapped in an eternal present of toil or display. Confined in lives they do not control, the teachers in Chekhov's two stories cannot link their pasts, presents, and futures into narratives they might live out and steer in different directions. Here, Collin shows how works of art can attend to particularities of moral experience, including teachers' moral experience, that are difficult to recognize and address productively using general concepts in philosophy.