This paper arises from conversations over several years about why we so value our experiences leading women’s writing groups in prisons and jails. We have a lot riding on this: we want to contribute to social and political change, and we want to continue this work because it gives us great personal satisfaction and pleasure. There is considerable literature questioning whether teaching inside does anything to oppose the prison industrial complex, or simply supports the status quo—making the institution “look good” or performing a “credentialing” for our students (Drabinski and Harkins, 2013; Foucault, 1979; Rafay, 2011; Rodriguez, 2010; Sudbury, 2009). We agree with Julia Sudbury (2009) that “there is no pure activist scholarship [or teaching] that is untainted by our social location within a global political economy that so deeply depends on policing, surveillance, and punishment” (p. 32). Yet, we believe our groups counter harmful aspects of carceral institutions. They reflect values based on care, empathy and non-domination, found also in feminist work and in indigenous and restorative justice healing practices that support relationships. They embody Susan Sherwin’s (1992) hope that “Through working and talking together, we can discover and pursue other models of relationships” built on connection rather than domination (p. 27). And because they focus on writing, they remind us of Ursula Le Guin’s (2014) insistence that “Any human power can be resisted and changed by human beings. Resistance and change often begin in art. Very often in our art, the art of words.”