Systemic oppression is a pervasive and insidious problem in U.S. society. In higher education, challenging oppression sometimes requires exposing how institutions perpetuate violence toward minoritized populations, passionate confrontations with people who have committed undeniably egregious acts or are key powerbrokers actively perpetuating systemic oppression, and disruption of the status quo. Reflecting on personal observations in higher education led the authors to ask several questions. What are higher education professionals teaching students about collective organizing and social activism? How are higher education professionals modeling toxic or constructive forms of activism through their own social justice advocacy? And, how can such conversations inform the ways in which higher education professionals engage students so that they are learning how to be the best citizens possible and maximize their positive impact on their communities and the world? In the current article, the authors aim to address these questions. The authors hope to spark more constructive conversations about how higher education professionals can be more thoughtful and healthier in how they approach activism and advocacy while supporting students in learning.