In this conceptual essay, I ask, what might happen when educators default to unexamined habits in their classrooms? How might we be ignoring the more creative pedagogical options, not for lack of good intentions but simply out of routine and tradition? I utilize John Dewey's ('Habit.' In "John Dewey: The Later works," edited by J. A. Boydston, Vol. 17, 298-309. Southern Illinois University Press, 1902/1990) exploration of habit as it provides a constructive lens through which we can think about our own pedagogy as I explore the negative role that habit can play for a thoughtful and creative practitioner. I then turn to assumption analysis (Brookfield, "Becoming a Critically Reflective Teacher," 2nd ed.; eBook edition, Jossey-Bass, 2017, https://bibliotheek.ehb.be:2191/enus/Becoming+a+Critically+Reflective+Teacher%2C+2nd+Edition-p-9781119050711) as a method to uncover hidden habits and argue that in an era of standardization, when so much might be recommended or even dictated to us, we need to continue to be vigilant about critically questioning our own approaches. To illustrate my assertions, I include examples from my own practice as a teacher educator.