Critical thinking is a catchword in educational studies and policy documents. It is usually considered a set of cognitive skills and argumentation competences, such as the ability to assess premises and make inferential connections between statements, but that is not the whole story. As an educational ideal, critical thinking goes beyond formal/informal logic and the individual’s capacity for reasoning; in the growing field of scholarship on the role and meaning of the concept in (higher) education, critical thinking has assumed psycho-social, ethical, political, and ontological dimensions. One of the “schools” of critical thinking is the criticality movement, according to which the paramount function of education is to produce critically thinking citizens. Cultivating openness, self-reflection, and critical action, it lays emphasis on our acting in the world and our responsibility for the world around us. This presupposes a kind of transformative learning that leads to the development from critical thinking to critical being. In pursuit of the criticality ideal of critical thinking in teaching the survey of American literature, this paper homes in on an important aspect of the pedagogy for critical being, namely, the cultivation of critical self-reflection, using a central text in the canon of American naturalism. With its multilayered structure of meaning, rich symbolism, ethical conundrums, character and situational dynamics, and complex relationship with determinism, Stephen Crane’s “The Blue Hotel” is a stimulating ground for critical self-reflection in literary studies.