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Preservice teachers (PSTs) often describe rather than apply knowledge in written reflection. Drawing on the concept of “wobble”—moments of disequilibrium that trigger reflection—this mixed-methods study examined conditions that advance PSTs toward application. We scored 43 reflections from a representative sample of junior-level PSTs in an educator preparation program using a four-level rubric. A repeated-measures t-test showed a significant jump from description to application between assignments two and three (p < .05). Qualitative coding identified two enabling conditions: (a) a fresh, concrete teaching experience and (b) alignment between course case studies and fieldwork. Findings refine theory on reflection and inform the design of clinically integrated programs that systematically connect coursework and practice for deeper novice learning and professional growth.