This essay focuses on the important, but often taken-for-granted, roles that mentoring and collaborative inquiry play in rethinking childhood studies and situates our work in a time of resurgent racism and xenophobia in the United States—as well as invigorated movements to affirm human rights and social justice. It represents a co-mentoring dialogue, spanning over a decade, about the complexities of embodying critical, activist scholarship within dominant (White, Western, heteronormative, and Global North) assumptions about childhood, families, and communities. Our co-interrogation of these deeply encoded assumptions has been driven by a shared question of how to span the seemingly disparate discourse communities of critically engaged scholars and mainstream early childhood professionals in a variety of community contexts. These efforts have been guided by learning from Indigenous and Global South epistemologies and Black and Chicana/Latina/Mestiza feminisms. To illustrate what continues to be a reciprocal mentoring relationship, we use critical personal narrative to discuss key influences, literature, pedagogies of place, and exigencies of sustaining critical childhood studies movements in the current moment.