This study explores the lived experiences of individualized and interdisciplinary students enrolled in a 4-year public university in the Upper Midwest region of the United States. Those enrolled in this individualized degree program are working adults with significant family, work, and life obligations. As Brookfield (2006), Knowles (1980), and Dewey (1903) indicated, adult learners want to be in charge of their education and find meaning in coursework that relates to their professional or out of school experiences. While this seems to be a common discourse for most of our learners, some also struggle with the complexity and uncertainty of directing one's own degree. This study, based on focus groups conducted as part of classroom activities, reveal how working adults find their individualized degrees to be student-centered yet constrained by university policies, experience the process as liberating and empowering while also anxiety provoking, and worry about the perception of an "easy" degree while striving for a rigorous and passion-driven one.