The conjunction of the pandemic and the intensification of social justice movements following the murders of George Floyd, Breonna Taylor, Ahmaud Arbery, and others helped create conversations around collective trauma and compassion. Within the academy, this has led to robust discussion of creating inclusive and compassionate classrooms. The growing body of literature on practices of critical, feminist, and anti-racist pedagogies provides useful insights into ways of creating an empowering and compassionate classroom. In this paper, I seek to consider how the past two years have shifted my pedagogy from one focused on critical thinking and the empowerment of individual students to a more classroom-community focused approach, designed to foster greater engagement, encourage collaborative knowledge-building and cooperative learning, and empowerment of students as both individuals and collectives to recognize and push against structures of power. This work will incorporate a review of critical, inclusive, and anti-racist pedagogies, followed by a discussion of practices and activities that I have implemented in several courses, including lower-division survey courses and upper-division cultural awareness courses—all of which are centered on Middle East history and interdisciplinary Middle East studies. This includes first-day activities that help students identify their roles in participating in and resisting structures within the classroom and in global contexts, small-to-large group activities around debates and source analyses, and "awkward discussions" designed to place students at the center of slow, deliberative, but ultimately deeply rewarding discussions on conflict, memorialization, race, and identity. Finally, I will incorporate student feedback and reflective autoethnography to assess the successes (and failures!) of these efforts to date.