People who are drawn to teaching college in prisons often see their work as a moral calling. They may be dedicated to promoting the right to education, to challenging systemic inequality, or to disrupting white supremacy. These commitments are valuable, and they come with certain risks. Idealistic celebrations of this work as liberative or transformative can contribute to a savior complex; they can exacerbate troubling power dynamics between free teachers and incarcerated students. They can lead teachers to overlook the ways that higher education in prisons depends on and reproduces aspects of carceral institutions that they oppose in principle. Other contributors to this volume have highlighted these risks. I believe we should be equally wary of the related tendency, common among academics committed to social justice, towards ascetic self-criticism. Teachers in prisons are likely to witness and, perhaps, participate in, events that challenge them morally. In this context, relentlessly self-critical attitudes can increase the risk of burnout and compassion fatigue. Even more, they can distract us from the day-to-day experience of our work and lead to harm to students and other people in prison with whom teachers interact.