Retirement marks a pivotal life transition that profoundly influences physical, financial, mental, and social well-being. While pre-retirement programs are designed to support individuals during this phase, many—including the program at PT X for managerial and executive employees—lack comprehensive, outcome-based evaluations. Current assessments predominantly focus on participant satisfaction, offering limited insight into the long-term effectiveness of these programs. This study addresses the critical gap by evaluating whether PT X’s pre-retirement program effectively prepares participants for retirement while identifying areas for improvement. Data collected through online questionnaires with 73% of the respondent were a pre-retirement program participants and 27% were non participants. Utilizing multifactor ANOVA, the research analyzed how program participation, private health insurance, financial literacy, health awareness, and financial readiness impact preparedness across four key dimensions of well-being. The findings reveal that participation in the program itself did not significantly influence the overall preparedness of pre-retirees in PTX. This result highlights the need for a more targeted and personalized approach to program content and delivery. By presenting a data-driven evaluation, the study provides actionable recommendations to enhance the program, ensuring it equips participants with the confidence and practical tools necessary for a seamless transition into retirement.