In a time of intellectual and emotional overload in education, this paper offers room for breathing through a pedagogy of emptiness from a Daoist perspective. It begins by introducing the concept of Daoist emptiness through three intertwining features--generative, transcendent, and inclusive--important for rethinking pedagogy. It then moves to four significant pedagogical implications: emptiness as opening pedagogical possibilities, pedagogical relationships in an empty space, self-transformation and self-transcendence in teaching and learning, and a playful pedagogy beyond dualism. First, emptiness opens pedagogical possibilities by clearing the ground and leaving space in the esthetic imagination. Second, pedagogical relationships in an empty space can be enacted through teaching without (or beyond) words, dwelling in time, suspending judgment, and creating space by cultivating the educator's inner emptiness. Third, an empty space of relationality provides a generative condition for the possibility of personhood re/formation and self-transformation. Fourth, a playful pedagogy in a creative flow from emptiness breathes improvisational lightness to unsettle dualism, dissolve rigidity, and give birth to students' new understandings, awareness, and relationships.