Over twelve years after a devastating decade-long civil war, Sierra Leone relies on its youth to serve as major drivers in transitioning the country from reconstruction phase towards sustainable development. However, inadequacy of the education system, which is relied upon for building youth capacity to engage with complex post-conflict issues, threatens this evolution. How young people are experiencing and conceptualizing these challenges in a rapidly changing landscape and the interaction of those perceptions with educational processes lacks sufficient investigation. Given that environmental conditions are known to influence human perceptions and that the current conditions have had a significant impact on citizens’ worldviews, such explorations are warranted. Employing qualitative approaches, this study investigated young people’s environmental perceptions, its relation to their future orientation, and perceived instrumentality of education for personal and community development in Koinadugu District (considered the least developed region of Sierra Leone). In addition adult stakeholders were interviewed to provide contextualized information relating to the research topic where documented data was limited. Results demonstrated that while young people had strong positive aesthetic and affective responses to their natural environment, the built environment was viewed and experienced as incongruent with their “life paths.” Findings show that person-environment misfit had a negative influence on perceived community futures. On the other hand, self-efficacy mitigated such effect for personal futures. In general, this study found that school goers viewed the education system as inadequate for preparing young people to engage in community problem solving or attaining future career goals. Those in vocational training were more satisfied with their education than their school-going counterparts. Sense of place, in particular “place attachment” appeared as a strong variable in young people’s narratives, indicating opportunities for a reversal of youth rural-urban migration and retention of a rural workforce.