This essay investigates philosophic trends of Russian modernism through an analysis of recently discovered author Sigizmund Krzhizhanovsky’s short story “In the Pupil,” which can be said to be a philosophic allegory. In order to understand its place in the history of Russian modernism, I read the story through the prism of three key allegories from Plato’s The Republic: the allegories of the sun, the line, and the cave. I argue that Krzhizhanovsky deconstructs the main postulates of Platonic philosophy by showing that the acquisition of knowledge and the act of writing inevitably lead to the loss of the subject’s ontologic wholeness. Krzhizhanovsky offers this insight as literature’s corrective to idealistic philosophy’s treatment of language and a foundation for a new, intersubjective ethics that takes the splintered subject as a given. This essay argues that reading the story as a paradigmatic text of (Russian) modernism is useful for understanding its philosophic complexities.