This article examines canonical author Kim Yujŏng’s only sustained piece of literary-critical writing with an eye toward rethinking the genre conventions which structure our perceptions of colonial-period Korean literature. In his “Thoughts from a Sickbed,” a wide-ranging essay written in epistolary form and published in the month of his death in 1937, Kim grapples with what I call empiricist discourse in the areas of science, love, and aesthetics and presents a critique of subjectivism and objectivism in all three registers. Kim takes issue with a naïve belief in the capacity of language to fully capture its referent, a tendency he finds basic to both naturalist and “new psychological” fiction. He argues instead for a mode of writing that confronts such assumptions with the impossibility of complete representation, a continual grasping toward always unattainable ideals of human knowledge and understanding. This study frames Kim’s engagement with empiricist discourse in the context of the more general crisis of representation which crossed ideological boundaries in the Seoul literary circles of the 1930s and suggests that Kim’s critique—and subsequent advocacy of ethical literary practice—points toward irony and idealism as categories through which the relationship between discourse and reality in colonial-period literary history might be productively thought.