Retirement can come with difficulties, particularly in the Philippines, where a considerable large number of seniors lived below the poverty line. Despite Social Security System (SSS) contributors expecting a maximum monthly pension of Php 20,000, most retirees lack adequate funds, highlighting the urgent need for effective retirement planning. This study investigates retirement planning among National Capital Region (NCR) private sector employees, focusing on factors like income, lifestyle, savings patterns, investment knowledge, health, and generational differences while considering demographic moderators such as age, sex, type of company (local/multinational), total years of work experience, years of work experience in the current company, and salary. The research, involving 204 participants, employed WarpPLS and PLS-SEM for statistical analysis. The results showed that investment knowledge, employee health, and generational differences significantly affect retirement planning. Additionally, demographic factors like age, sex, company type, work experience, and salary play key roles in shaping retirement outcomes. These findings provide valuable insights for policymakers, employers, and individuals, emphasizing the need for customized retirement strategies to meet the diverse needs of NCR private sector employees.