Very little can prepare a new professor for the angst associated with planning a course full of polarizing content in an online learning environment. Each assignment, discussion board, and course reading is a learning opportunity that can either lead to enlightenment or evoke strong negative reactions that hinder student growth for the entire semester. The primary mode for dialogue in an online course is the discussion board but the discussion board presents unique challenges when the course content is potentially controversial. The professor is not always available to model effective communication and referee discussions that evoke strong, emotional reactions. Further complicating matters is the fear associated with creating a course that generates negative course evaluations—a major concern for a tenure-track professor. The motivation behind this article is to reflect on my first attempt at teaching a course designed to critique social justice issues in education. The article chronicles my planning process, my successes, my fears, and ultimately my own guilt at not pushing the envelope far enough to truly challenge my students to think critically about their own experiences with power and privilege.