In this essay, Meaghan Dougherty reflects upon how research she conducted on social service workers’ transition from post-secondary education to work has influenced her approach to teaching and learning. Drawing parallels to her own transition experiences, she examines how key findings from the research—including transition being a continual process, “not knowing” being an asset, and the importance of truly “being with” others—have important implications for relational practice and pedagogy. Reflecting on her developing approach to teaching and learning, the author encourage educators to rethink the importance of relational processes in educational encounters. Critically questioning our role as educators generates possibilities for social change; we can disrupt ideas about education which are taken for granted and transgress dominant ways of “being” in the classroom.