Faculty and administrators often present risk-taking as something honors students must do, but rarely do they take risks themselves. In an ideal situation, communal risk-taking would subvert institutional power dynamics, free students from grade-associated anxiety, and enable them to build dynamic partnerships with faculty. This paper discusses how one honors college piloted self-grading in the second semester of its first-year seminar as a mechanism of liberatory learning for both faculty and students. While self-grading was originally intended to provide increased freedom for risk-taking, in truth it led to increased anxiety in students and high levels of frustration for faculty. This pilot program demonstrated the underlying flaws in the concept of risk-taking and ultimately failed. Although faculty may have good intentions, simply removing grades does not remove internalized, perceived judgment. Real risk-taking requires all parties to participate with enthusiasm and to adapt when necessary in order to be successful. While self-grading did not accomplish its original aims, the process demonstrated previously underappreciated underlying cultural tensions that fundamentally affect student and faculty freedom and risk-taking, displaying how deeply entrenched the social mores are for honors faculty and students, as well as how much work is left to encourage risk-taking by both groups.