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Drawing from a larger study, this project explores the strategies transfer students use as they navigate graduation timelines at a public, four-year R1 university. With 62% of students (n=556) reporting stress related to their timeline, and 47% noting financial barriers, this proposal highlights how institutional timelines can unintentionally create additional challenges for our transfer populations, particularly first-generation students. Despite institutional challenges (e.g., limited course offerings), students emphasized the value of staying beyond two years, with 68% of those reporting meaningful academic and personal growth. We urge educators, administrators, and policymakers to reimagine policies that define "on-time" graduation, and consider adopting student-informed models of success that recognize the value of flexibility, engagement, and belonging in transfer students’ educational journeys.