Critics of contemporary higher education frequently overlook an important dimension of assessment of student learning: namely, the social and economic consequences used to justify the assessment measures in the first place. This essay argues that meaningful student assessment must take into account the unintended, transferable utility of liberal higher education. The authors, from a large master’s-comprehensive state university, use a recent survey of alumni of their English degree program from as far back as the 1960s to assess the importance that the degree has had in the lives of former students. Believing that disciplinary differences may help us to understand the navigational courses that emerge as seemingly nonlinear and unpredictable paths from the college degree to the life after college, the authors use students’ responses to identify how, where, and what students have used from their English courses in their most recent professions and, in turn, the limitations of current value-added assessments such as the Collegiate Learning Assessment (CLA).