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Debates surrounding class inequality and social mobility often highlight the role of higher education in reducing income inequality and promoting equity through upward social mobility. We explore the lived experience of social mobility through an analysis of 11 semistructured interviews with Canadian academics who self‐identified as having working‐class or impoverished family origins. While economic capital increased substantially, cultural capital and habitus left many feeling like cultural outsiders. Isolation—both chosen and imposed—reduced professional networks, diminishing social capital. Caught between social worlds, participants mobilized symbolic capital in moral boundary marking, aligning themselves strategically with either their current class status or their working‐class roots. While upward social mobility is a path toward reducing economic inequality, the lived experience of social mobility suggests it may exact a high emotional cost.