Teaching a course entitled "Introduction to Theories of Education" requires that one practice what one is preaching. We describe an attempt to organize and provide undergraduates enrolled in an introductory course of 300+ students, with a viable, yet more collaborative and "product-based" alternative to the familiar lecture and test format. This qualitative study considers various forms of feedback that were elicited from both students and the course teaching assistants regarding the learning outcomes facilitated or hindered by this alternative format. Our analysis offers insight into some important ways the particular learning activities promoted in this course design intersect with larger institutional norms that infuse organizations (like universities) with social value, and how students negotiate the university experience. Findings suggest that "good students" spend considerable energy learning to conform to what they believe to be their instructors' expectations, often at the expense of learning-with-understanding. However, learning-with-understanding may also be encumbered by the ambiguity or uncertainty that accompanies the removal of clear and explicit expectations. Tentative suggestions are offered explaining why and how some students gained proficiency in goal-formation and metacognition while simultaneously overcoming a sense of ambiguity or uncertainty.