UNLABELLED: Phenomenon: Medical students in the United States face increasing educational debt because medical education costs have risen while public investment in higher education has declined. Contemporary students borrow more money and accumulate debt far surpassing that of previous generations of physicians, and both interest rates and terms of loan repayment have changed significantly in the last decade. As a result, the experiences of medical students differ from the experiences of physician educators. Little is known about how contemporary medical students view their debt in the context of career planning. Understanding contemporary U.S. medical students' lived experiences of educational debt is important, because high debt levels may affect medical students' well-being and professional development. APPROACH: The study's purpose was to explore contemporary students' views of their debt in the context of career planning. In 2012, 2nd-year medical students enrolled in a health policy course at one medical school were invited to write an essay about how debt influences their career choices. The authors analyzed 132 essays using immersion and crystallization and iterative, team-based coding. Code-recode strategies, member checking, and reflexivity ensured validity and rigor. FINDINGS: Three themes emerged about the meaning of debt: debt symbolizes lack of social investment, debt reinforces a sense of entitlement, and debt is a collective experience. Four approaches to debt management emerged: anticipation, avoidance, acceptance, and disempowerment. Insights: Medical students' views of debt are more complex than previously reported. Medical educators should recognize that many students experience debt as a stressor, acknowledge students' emotions about debt, and invite discussion about the culture of entitlement in medical education and how this culture affects students' professionalism. At the same time, educators should emphasize that students have many repayment options and that regardless of specialty choice, most physicians repay their debts without significant difficulty. Further exploration is needed of the relationships between the amount of debt owed, students' attitudes toward their debt, and other student characteristics. Because students experience debt in a range of ways, more nuanced approaches to understanding and reframing student perceptions of debt are necessary.