The purpose of this study was to test the hypotheses that psychological well-being is associated with healthcare and financial decision making in older adults and that this association varies by the level of cognitive function. Participants were 1082 older adults (97% non-Latino White; 76% women; mean age = 81.04 years; SD = 7.53) without dementia (median MMSE score = 29.00, IQR = 27.86–30.00). In a regression model adjusted for age, gender, and years of education, higher levels of psychological well-being were associated with better decision making (estimate = 0.39, standard error [SE] = 0.11, p < .001), as was better cognitive function (estimate = 2.37, SE = 0.14, p < .0001). In an additional model, an interaction of psychological well-being and cognitive function was significant (estimate = −0.68, SE = 0.20, p < .001), such that higher levels of psychological well-being were most beneficial for decision making among participants with lower levels of cognitive function. Higher levels of psychological well-being may help sustain decision making among older persons, particularly those with lower levels of cognitive function.