What happens when teachers perceive a growing rift between their pedagogical practice and their students' lived experiences? How do teachers respond to the uncertainty that such a "relevance gap" can create? In a climate in which literacy research is often pressed to address the achievement gap and to contribute to a sense of certainty, this study explored the relevance gap experienced by teachers in their teaching of writing and the ways that teaching with uncertainty contributed to their practice. Situated in theories of curriculum as "currere," local knowledge of practice, and pedagogy as assemblage, the article focuses on the theory and practice of four educators who teach writing in very different and diverse contexts. The rhizo-textual analysis of the data inspired a process of making assemblages to explore context, positionality, and power in teachers' identities as writers and teachers of writing. Two such assemblages are described, one exploring struggle and the other possibility. In the struggles and uncertainties they experienced, each teacher found new possibilities in different places: in the land, in slam poetry, in story, and in film. Our mappings and analyses suggest that teachers can create new pedagogies of becoming for them and their students by burrowing into uncertainty, process, and social critique.