In a larger study about academic affairs and student affairs partnerships for diversity and inclusion aims, participants were characterized as social gadflies (LePeau, 2015). These participants effectively pushed the status quo in their respective campus environments by unearthing inequities and working collaboratively to infuse diversity and inclusion initiatives in the curriculum and cocurriculum. The purpose of the current study was to examine the experiences and characteristics of the social gadflies. Findings reveal how participants' experiences growing up in the Civil Rights Era, teaching in alternative K-12 education, and studying diversity and equity issues in graduate education influenced how they experimented with job roles and collaborated in their work to enact diversity and equity initiatives in their campus environments.