Rural adolescents approach the transition out of high school with individual concerns about making an emotionally or financially expensive "mistake," family concerns about young people leaving home, and national and local concerns about declining rural economies and out-migration. The literature concerning this topic considers factors that influence youth aspirations in rural areas, such as economic barriers, the way higher education is valued, and perceptions of rural places as lacking in opportunity. However, there has been little study of the myriad interpersonal, emotional, and self-identity inputs that are part of the decision-making processes of rural emerging adults, and little is known about how the aspirations of rural youth play out over time. This article, based on the findings of a qualitative longitudinal study, considers the way rural emerging adults weighed options, understood constraints and opportunities, and took action on behalf of their aspirations to make something meaningful of their lives. Research participants were engaged in a process of decision making that was multifaceted, nuanced, and purposeful, and the results of the research made it clear that we need to think beyond the dualisms of staying or leaving, college or not. Counselors must be prepared to "stay complex" and help rural emerging adults anticipate ecological transitions, find coping mechanisms, and cut through binaries to explore alternative pathways, creative identities, and multiple meanings of success.