In 2020, a global pandemic and egregious evidence of systemic injustice have catapulted the U.S. into turmoil. Carolyn Dinshaw identifies these disruptions as signs that change is needed for all institutions, including higher education. In her meditation about these needed transformations she notes that substantial experimentation is integral to successful and beneficial change. Inspired by the educational approach advocated by the Muscatine Report—whose eponymous author is familiar to Chaucerians—Dinshaw urges that we once again embrace experimentation. Our changes need to be bold and we need to be ready to fail. Like Charles Muscatine and others who designed the experimental Strawberry Creek College at the University of California at Berkeley, educators must seek structural change in order to make the university truly a place for higher learning.