In this article, we review the appropriateness of ‘mindfulness’ as an educational goal and explore what it means to cultivate mindfulness as a disposition, that is, as an enduring trait, rather than a temporary state. We identify three high-leverage instructional practices for enculturating mindfulness: looking closely, exploring possibilities and perspectives, and introducing ambiguity. We conclude by exploring what it might look like to cultivate the trait of mindfulness within individual classrooms. This report includes a review of an experimental study of ‘conditional instruction,’ which explores mindfulness as a state, and then draws on a series of qualitative case studies of ‘thoughtful’ classrooms to provide an example of conditional instruction as it might serve to develop a disposition of mindfulness.