This study compared levels of concern, spending, and use of external support by working status among older adults in the U.S. during the COVID-19 pandemic. It assessed whether work influences these variables related to wellness. Data from 2489 older adults from the 2020 U.S. Health and Retirement Study were analyzed using multiple linear and logistic regression. Older adults who worked had lower concerns about the pandemic (β = −0.28, p = 0.048), were less likely to increase their spending (OR = 0.74, p = 0.041), and were less likely to use external support (OR = 0.50, p < 0.001). Use of external support increased with age (OR = 1.04, p < 0.001) and increased spending (OR = 1.32, p = 0.019). Married older adults were less likely to increase spending (OR = 0.75, p = 0.007) and had lower concerns toward COVID-19 (β = −0.28, p = 0.011). Higher levels of concern were reported among women (β = 0.31, p = 0.005) and participants who had friends or family members diagnosed with COVID-19 (β = 0.51, p < 0.001). Women were more likely to use support (OR = 1.80, p < 0.001). Work appears to bolster older adult wellness outcomes.