Addressing how employment impacts older adults, including their psychological well-being, we contribute to the study of this topic by examining the association between paid work in community-dwelling older adults and their depressive mood, while considering the extent of their financial pressure. Methods: The data are from the Kashiwa longitudinal cohort study, with a 2014 baseline and a 2016 follow-up. Of the 1308 participants in the 2014 survey, 781 people were included. We conducted binary logistic regression analyses stratified by economic status with regard to the extent of the financial pressure experienced. The independent variable of interest was paid work in 2014, and the dependent variable was the extent of depressive mood (a score of 5 or more on the Geriatric Depression Scale 15) in 2016. Results: Paid work was associated with lower odds of depressive mood among those under financial pressure (odds ratio [OR] 0.46, 95% confidence interval [95%CI] 0.26, 0.81), whereas for those financially stable, we did not find an association between paid work and odds of depressive mood (OR 0.99, [95%CI] 0.26, 2.63). Discussion: We evidence that for older adults under financial pressure, employment supports the maintenance of their psychological well-being. We contribute to the literature by understanding when employment is beneficial for older adults, which is important in developing appropriate older adult employment social policies.