This study presents the story of a collaborative, interdisciplinary curriculum project, called the Quest Program, now being implemented at a suburban New England high school. The program, based loosely on the tenets of the Coalition of Essential Schools, resembles in many ways the growing number of grass-roots change efforts in schools around the country: It was a project embraced by teachers, supported by administrators, and collaboratively designed with college faculty. This study tells of the school's painful, ambiguous, and circuitous route toward partial and subjective success. In so doing, it contributes to the presently scant literature that candidly documents the practical reality of institutional change. The study concludes with a series of understandings that highlight the problematic nature of both instituting and researching such reform efforts.