This design-based study explored what happens when literacy educators from across the country intentionally create learning events that engage preservice teachers in exploring culturally proactive pedagogies (CPP). After each event, researchers met via video conference to discuss preservice teachers' responses, which guided future pedagogical decisions. The findings, framed by Pose, Wobble, Flow, examine how preservice teachers posed, in stating their beliefs specific to CPP, wobbled in those beliefs throughout the semester, and in some instances found "flow" by persisting through the wobble to develop a more nuanced understanding of CPP. Implications for teacher education are discussed.