In this essay, I offer some thoughts on the problem of self-reflexivity in critical theory, with special attention to the way in which this problem is thematized in The Authoritarian Personality (1950). The problem of self-reflexivity is a defining feature of any social theory that means to account for the conditions of its own possibility within the society it describes. I argue that The Authoritarian Personality is less a study of distinctive and socially isolable personality “types” and more concerned with the rise of “conventionalism” as a generalized problem that afflicts all of modern society. In this respect the book shares in common a major focus on the problem of conformity that was also studied by other classic mid-century works of sociology. The question of conventionalism, however, brings into sharp relief a dilemma of self-reflexivity, namely, how can the researchers account for their own critical posture if the world they describe encourages conventionalism and disables criticism? By examining Adorno’s comments on the themes of realism and utopia and the distribution of these attributes between high-scorers and low-scorers, respectively, I offer one possible answer to this dilemma.