This study explores the differences in the financial and psychological satisfaction of three age cohorts and the factors contributing to those satisfaction levels among Korean baby boomers and older workers. The data of 1555 participants came from the Korean Welfare Panel Study from wave 1 (2006) to wave 8 (2013). The Chow test and multiple regressions were utilized to explore whether impacts differed by birth cohort and to identify unique factors associated with financial and psychological satisfaction. The results showed the ‘satisfaction paradox’ – a positive relationship between age and the financial satisfaction. Moreover, working longer played an important role in reducing depression, but not in increasing financial satisfaction.