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This paper presents a comparative analysis between mindfulness meditation on the one hand and democratic education on the other, through the postmodern lens of meditative inquiry. From the perspective of a mindfulness practitioner, I narrate my own early spiritual and educational paths, before presenting the essence of mindfulness meditation based on the teaching of two prominent Vietnamese Zen Masters Thich Nhat Hanh and Thich Vien Minh. Then, I survey democratic education theories with an emphasis on self-directed learning, which was initiated by Maurice Gibbons (1978) and later developed further by some visionaries/scholars/practitioners such as Arnold Langberg (2010) and Rick Posner (2009). Then I move on to narrating my ethnographic field study at a democratic school named the Jefferson County Open School in Lakewood, Colorado and analyzing the self-directed learning principles behind it, based on my observation of the school activities, and my interviews with the school teachers, administrators, parents, students, and alumni. My conclusion is that despite their multiple superficial differences, mindfulness meditation and democratic education are surprisingly similar at the core with three primary common features: non-judgment, non-becoming, and non-control.