University instructors are increasingly drawing on active learning exercises to engender critical thinking skills among students. In this article, we introduce the design and implementation of an active learning exercise about mobility and transportation that we assigned in an introductory human geography class at the University of Georgia. The students' responses and the survey instrument we used to assess the effectiveness of the exercise revealed disappointing results and caused us to think carefully about the role of positionality in designing active learning exercises. In this article, we argue that we need to understand privilege—particularly class privilege—in order to design effective assignments.