Educational theory and practice have been focusing on educating students as to “how to think.” Yet, contemporary neuroscience and psychological research reveal that many of our waking hours are spent in a state of “mind-wandering” characterized by uncontrolled thoughts that have little to do with our concrete present engagements. Research shows that mind-wandering has mostly negative effects on our well-being and performance. This paper explores the educational implications of this curricular blind spot for mind-wandering and implies that a student's mind internally produces content that presumably overrides the curriculum offered in the classroom. Based on Dewey's philosophy of education and cognitive theory, mind-wandering is depicted here as a two-layered habit that may entrench us in our past and possibly create internal resistance to educational change. Nested within a contemporary discourse of mindfulness practice, the article explores the pedagogical mechanisms of mindfulness as ways of rectifying both layers of this human predicament.