Abstract: This study investigated how prior career experiences imprint on individuals' behaviors, particularly in military contexts, shaping their transition into civilian life upon retirement. Resistance to change, one's tendency to resist or avoid making changes, and personal sense of power, one's perception of their ability to influence people and resources, often become by-products of military institutionalization, influencing military-to-civilian retirement transition and well-being. A moderated mediation model was proposed wherein personal sense of power would moderate the indirect relationship between resistance to change and well-being, mediated by transition difficulty. The sample was comprised of retired Indian Army personnel (N = 256). Confirmatory factor analysis validated the scales culturally, and Hayes' PROCESS Macro was used to test moderated mediation. Findings reveal that resistance to change and transition difficulty negatively affect well-being. Moreover, transition difficulty partially mediates the relationship between resistance to change and well-being. Notably, personal sense of power moderates this mediation, acting as a buffer. The study underscores the significance of organization-relevant dispositional factors in comprehending the challenges of military retirement and their implications for overall well-being. The study provides recommendations for addressing dispositions such as resistance to change and personal sense of power through interventions like preretirement counseling, scenario-based exercises, growth mindset training, and confidence-building workshops to help veterans navigate transitions more effectively.