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This study examined family and individual processes influencing the future expectancies of adolescents (N = 345) from an economically stressed rural community. The anticipated timing and sequencing of key role transitions (school completion, job entry, marriage, and parenthood) were examined for each gender. In addition, factors contributing to individual differences in expected timing were examined, and gender differences in predictors were tested. Results indicated that rural adolescents' expectancies about adult role transitions diverged somewhat from societal norms with respect to timing. Family background and relationships, adolescents' attitudes and behaviors, and educational aspirations all contributed to individual differences in expected timing, with somewhat different factors being salient for boys and girls. These findings provide clues to the psychological processes linking adolescent experiences to the construction of the adult life course.