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Using data from sixty-eight interviews conducted with men and women raised in rural counties in Pennsylvania, we ask how growing up in rural settings shapes people’s aspirations regarding work over three periods. We find that participants’ early aspirations during their late teens were shaped by rurality, gender, and class. During the transition to adulthood and again during an unemployment period, searching for work in rural areas with a shrinking economic base, participants adjusted their early aspirations. These adjustments were shaped by their attachment to rural locations, their gender, and class and exacerbated existing structural inequalities in their local labor markets.