Critical pedagogy, by brealdng down the boundaries between the academy and society, creates opportunities for deep and transformative learning. Inspired by bell hooks' call to engage the hearts as well as the minds of learners, this essay demonstrates two teaching methods that engage college students in intellectual inquiry that potentially challenges and undermines societal power relations. The first literally broadens the walls of the classroom through community-based projects. The second constructs an in-class learning experience that cultivates inter-personal perspective taking by simulating arbitrary and systemic inequality. Both approaches inherently question received relationships of power, within and outside of the classroom, by creating opportunities for learners to transgress the boundaries imposed by individual experience, enabling them to envision connections across social and economic difference. Through active learning experiences that connect affective responses to new learning, students gain insight into the ways systems of domination construct social privilege and structural oppression. Urging all of us to open our minds and hearts so that we can know beyond the boundaries of what is acceptable, so that we can think and rethink, so that we can create new visions, I celebrate teaching that enables transgressions—a movement against and beyond boundaries. It is that movement which makes education the practice of freedom. bell hooks, Teaching to Transgress (1994: 12)