Role sequencing refers to the ordering of social roles. According to the normative order hypothesis, adults who follow a certain sequencing of their social roles will be better adjusted than their peers who follow other life course patterns. The normative order is defined as first entering the paid labor force, getting married, and later having children. This study tests this hypothesis by analyzing retrospective life history data from three subsamples of adults who completed the 1987–1988 National Survey of Families and Households: (1) married, working parents; (2) divorced, working parents; and (3) married, unemployed parents. The findings indicate significant race/ethnic (black/white), gender, and cohort differences in the type of role sequencing patterns that are conducive to positive mental health. For example, African Americans who work first, then have children, and later get married report better mental health than their peers who followed the normative order. White men and women seem to benefit from following the normative course of role transitions. Among women, however, the psychological benefits of following typical life course patterns are especially evident among those born during the baby boom.