This article juxtaposes the notion of "wuwei" in Daoism and philosophical principles of self-organization in systems theory to re-imagine classroom dynamics in which pedagogical relationships, students' interactions with texts, and peer interplay come together to enable an open system of education, learning, and growth. "Wuwei" is a way of governing and leadership, while self-organization is the emergence of new structures at the global level as a result of local interactions. The combination of top-down and bottom-up processes contributes to create a dynamic classroom. The contemporary Neo-Daoists' concerns with creating conditions for "wuwei" to happen can be addressed by principles of self-organization, while "wuwei" provides a philosophical underpinning that is informative to systems theories. This article first introduces the Daoist notion of "wuwei," then articulate important principles of self-organization theory, and further juxtapose the two in both resonance and dissonance in four aspects: the role of change, the role of diversity, the role of the individual person, and the role of the teacher's "wuwei" leadership in the self-organizing classroom. In the last section, the article discusses how to shift classroom dynamics toward emergent, relational, and creative pathways, including creating conditions for self-organization and "wuwei" to happen in the classroom.