The process of defining and redefining both one’s self and one’s community is a core feature of the Jewish experience. Take the strict halakhic interpretation of the “essential” pieces of Jewish identity: that the child of a Jewish mother is a Jew, and that the defining features of Judaism are found as mitzvot in the Torah. As communities have diversified, some have chosen to revisit, question, and modify even these seemingly “core” or “absolute” tenets. As our Jewish world diversifies, so too does the conflict and tension around negotiating our collective Jewish identity. Drawing a boundary can be tricky, exclusive, confusing, or alienating for educators and learners alike, especially in settings that integrate more and more Jewish diversity. It is therefore necessary for educators to navigate that conflict and tension constructively: to consciously and responsibly engage in the very Jewish process of negotiating our individual and collective identities. This pedagogy is meant to clarify and improve the way we engage in that process and, ultimately, to help make Jewish educators more nimble, resilient, effective, and responsive.