This article describes a data-driven approach to contextualize geography subject matter using student aspirations and workforce data. To test this teaching strategy, undergraduate students in two world geography courses taught at Texas State University were surveyed and interviewed about their career and life aspirations. Using this information, the course instructor selected relevant geography resources and applications using workforce data obtained from a sample of geographers employed in private and public sectors. Over the semester, students encountered those applications through class presentations, videos, and individual advising sessions. At the end, students completed a post-test survey. Resulting datasets offered the instructor a means to reflect upon and select geographic content that is accessible and applicable to what students aspire to be and do in the future. Analysis of the pre- and post-test survey data indicate positive gains in student attitudes but suggest additional culturally relevant pedagogical enhancements are needed to account for student diversity and context. The article concludes with a critical assessment of how future instructors might leverage aspirations and workforce data to address the underrepresentation of women and minorities in the discipline and workforce.