The Maoist regime has conventionally been understood as a totalitarian apparatus hostile to the individual. Yet the mass dictatorship also saw the proliferation of guidebooks on how to write a diary. This article is a pioneering exploration of these didactic texts, situating them within a longer Chinese tradition of popular subjectivation. A close reading of the guidebooks in light of their Republican predecessors suggests that the regime simultaneously anticipated the individual’s role as revolutionary agent of change and viewed it with trepidation. Prescribing paradigmatic frameworks for constructing socialist subjectivities, the manuals propagated journal-keeping as a political routine by which to shape the writer’s life and selfhood. Central in these teachings was the desire to mobilize yet monopolize the individual’s conscious agency. At once empowering and constraining, the “how-to” books rendered creative self-reflexivity indispensable—albeit dangerous—to the Maoist agenda, revealing a deep-seated anxiety of the state about socialism’s modern legacies.