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When reflecting on my first year teaching, I realized that while I wanted to be an educator dedicated to antiracist, culturally competent teaching, I often fell short. As I entered the 2023-2024 school year, I sought to center criticality in my classroom. Thus, my research question was: How can my students and I co-construct a community in which we consider evolving positionality in our ongoing dialogue about power? Inspired by the work of bell hooks, Tema Okun, Gholdy Muhammad, and Matthew Kay, I emphasized building community, engaging in identity work, and developing dialogue skills in my sophomore English course. During the practitioner inquiry process, I encountered resistance from students, and I experienced firsthand that when attempting to build a liberatory classroom, power structures and relationships in the wider world inform student engagement. This was especially visible during the community-building process; students viewed sameness as a prerequisite for community rather than a site of shared struggle. Nonetheless, students’ work throughout the course illustrated that their consideration of systemic oppression expanded. As their questioning skills developed, students increasingly used dialogue to co-construct knowledge and interrogate power systems. As I continue to grow as an educator and reflective practitioner, I hope to push students beyond critical thinking and into criticality while holding space for joy to blossom.