This dissertation explores the role that shame plays in schools in the United States, both historically and today. Through utilizing the Scholarly Personal Narrative (SPN) arts-based inquiry method, I consider my own encounters with shame both as a student and teacher, and position these stories as a jumping-off point to further investigate the relationship between shame and school. I argue that, contrary to traditional Western perceptions, shame is a risky and unpredictable experience, which does not reliably lead toward moral improvement. Shame is deeply embedded into American educational institutions, and thrives in schools through three primary pathways: through overt shaming practices and methodologies; though a model of deficit-based thinking systematically applied to students; and through a perpetuation and magnification of the pre-existing shame that students bring to school with them from their lives outside of the classroom. In order to teach students to push back against unhealthy experiences of shame, I argue that teachers should seek to induct students into a "mindset of enoughness" as well as seek opportunities to practice what Simone Weil calls "attention," a practice of openminded suspension of active thought that allows for the world to enter an individual. Practicing enoughness and attention in the classroom can support students in developing their skills of listening, connection, and imagination, which can help students move away from the isolated conditions that foster shame. Ultimately, all educational stakeholders should be educated in the complexities of shame, its potential consequences, and possible methods of subverting shame in educational spaces. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]