In this paper, six adult allies (comprised of four academic scholars, one in-service teacher, and one community-based teaching artist) reflect on what it meant for them to learn from the wisdom of eight years of intergenerational inquiry led by youth. The authors examine how youth researcher-activists make meaning of their realities within this sociopolitical moment, the exigency of their needs, and the self-examination of their roles within an intergenerational space of resistance work led by youth. To do this, the authors draw on the "cypher," a cultural practice within hip-hop communities, as an analytic, pedagogical, theoretical, and methodological tool to support decolonial approaches to deeply examining the experiences and literacies of both self and community. As the authors draw on the ethos of the cypher as a decolonial approach to examine these questions, the narratives that are evoked demonstrate the power of intergenerational inquiry to equip youth and adult allies to disrupt the status quo and be positioned to design educational futures that rest on freedom.