The purpose of this paper is to theorize the understanding of teaching quality from a critical pragmatist perspective by focusing on teaching as a habit. The research question is: In what ways is it possible to develop an understanding of teaching quality by turning speculative pragmatist attention to teaching as a habit?  The experiences shaping our habits are characterized by continuity. Dewey explains the continuity of habit in terms of that “every experience enacted and undergone modifies the one who acts and undergoes”, and this modification affects the quality of subsequent experiences (Dewey, 1991a, p. 18). Pedwell (2021) highlights these dynamics of habit and notes that minor processes within habits may carry an embryo of social change. The situations in which the habits take place are moving occurrences that enable new capacities and collectives to emerge. Pedwell argues that it is only through habits that we can develop social change that is robust enough to be part of everyday social life. Creativity is an integral part of the speculative aspect of habit, because this “speculative” aspect of pragmatism is made possible through continuities of experiences “which incorporate both the constraints of the independently real and the creative activity of the human organism” (Rosenthal, 1988, p. 313). Dewey (1984) claims that experimental inquiry within experience is characterized by action, ideas, and consequences, implying that the outcome of the experimental inquiry is a new situation. The speculative aspect thus points to an opening for changes in current conditions or habits.