This study examined the residency aspirations of rural youth in the context of the globalized economy. Past research on the outmigration of rural youth pointed to academic achievers being pushed towards pursing higher education and leaving the community for white-collar careers. Gains in technology, connectivity, and other features of the modern economy open rural locales to new possibilities from remote work in knowledge-worker career fields to the ability to tap into the global marketplace. Given these temporal changes to the rural circumstance, this study sought to investigate how the career aspirations of rural students were being influenced, and correspondingly, how that influenced their plans for settling down in the future. Set in the Northern Forest Region, this natural amenity rich rural community once thrived with relatively high-wage blue-collar jobs at its economic core. This collective case study involved interviews with five high school seniors, a parent of each student, and an educator or other influential adult identified by the student. Perceptions regarding careers and employment opportunities were found to be the leading driver in shaping residency aspirations. Despite positive feelings towards rurality and desires to reside in non-metropolitan areas, participants appeared to believe that quality employment opportunities were not possible in their hometown. The recommendations consider how schools and communities might work in partnership to cultivate place-consciousness while fostering careers that leverage today's more placeless economy.