This chapter is a critical reflection essay that uses an ethnographic approach to document the challenges and rewards of interdisciplinary team-teaching at a higher education institution from the perspective of a faculty member who conceptualized and served as lead instructor of the course, The Sustainable City. This course was initially taught by a team of seven faculty from different disciplines, following a radical team-teaching model in which each instructor contributed equally, shared class periods, and interacted with each other and students with the goal of exposing students to the ways in which different disciplines solve problems around sustainability. This analysis, spanning over a decade, includes the rise and decline of interdisciplinary team-taught sustainability courses at George Washington University between 2012, when this teaching model was instituted as a cornerstone of a new minor in sustainability, through 2023 as the future of team-taught courses at this institution has been thrown into question. Lessons learned include useful pedagogies that encourage students to think critically and become comfortable in conceptual complexity, including modeling socratic discussion and placed-based learning activities as well as recognition of the outsized time commitment required to integrate lectures, activities, and assessments between faculty and disciplines in a team-taught interdisciplinary course. The analysis ends with a cautionary note on the need for adequate institutional support vital for the success of such a unique, rewarding, and challenging endeavor.