We explore women's psychological well-being in late midlife in relation to childlessness and timing of entry into motherhood. Using two U.S. surveys, Health and Retirement Study (HRS) (1992) and National Survey of Families and Households (NSFH) (Sweet, Bumpass, & Call, 1988), we assess the well-being of childless women in their 50s compared to mothers with early, delayed, or normatively timed first births. We focus on the cohorts born between 1928 and 1941, who experienced strong normative pressures during the baby boom with regard to marriage and child-bearing. We find few differences among childless women but lower well-being among early mothers, related to singlehood and poorer socioeconomic status. Unmarried mothers are significantly disadvantaged regardless of maternal timing, controlling for socioeconomic status. Current maternal demands are independently related to well-being and help to explain observed differences in family satisfaction. Overall, childlessness and off-time child-bearing are related to midlife well-being through their link with more proximate factors, particularly current marital status, health, and socioeconomic status.