This article shares and examines the challenges, findings, and lessons learned associated with embracing peaceful leadership styles during the first two years of a partnership between a failing K-12 urban school district and a university in the United States. The ongoing daily leadership issues that influenced, but were beyond the scope of, the partnership are also explored. Through the individual and collective lens of six educational leaders (K-12 and higher education) who embraced leadership feminist practices embedded in structures of difference, Buddhist philosophies, equity, and social justice, this study examines and illustrates the administrative efforts associated with "going against one's grain" when faced with the proverbial brick wall.