Chapter 4 mobilizes second-order cybernetics theories that were first adopted in 1960s social sciences as a comparative framework for reading Gertrude Stein’s quasi-ethnographic writing about American culture. Love pairs Stein’s work with writing by second-order cybernetic anthropologists Margaret Mead, Gregory Bateson, and – most extensively – Mary Catherine Bateson. Love illustrates how Stein and M. C. Bateson both employ (a) the term “composition” as a framework for understanding the everyday habits of behavior that constitute American cultural identity, and (b) a combination of seemingly repetitive representational strategies and juxtapositional contexts as platforms for cultivating self-reflexive cultural awareness. They see this perspective as increasingly necessary within the twentieth century’s technologically complex networks that require us to respond in creative and flexible ways to our ever-changing circumstances. The chapter positions Stein’s work in dialogue with emergent social scientific strategies for cultural observation and analysis, and therefore as an important precursor to the anthropology-based theories at the forefront of cybernetics’ second-order turn.