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This qualitative study explores how career transitions in higher education and the military function as parallel systems of socialization, identity reconstruction, and worldmaking. Drawing on my professional shift from Assistant Dean of Student Affairs to Site Lead and Employment Navigator for the U.S. Department of Labor’s Transition Assistance Program (TAP), I employ autoethnography, document analysis and researcher-generated visual field notes to examine how assessment practices shape belonging and adaptation. Grounded in Durkheim’s concepts of solidarity and anomie, the findings reveal that universities and military bases deploy assessment as a mechanism of repair, transforming uncertainty into measurable readiness. This research bridges military and educational sociology, offering a reflexive model of adaptive assessment that illuminates institutional legitimacy and resilience amid change.