Objective: Most youth in Sub-Saharan Africa are not enrolled in school. Although more youth are enrolling in school, they are increasingly less likely to complete their primary and secondary schooling. Similarly to many other African nations, Tanzania has an estimated out-of-school population of 49% of youth despite massive post-millennium investments which have significantly raised enrollment rates. Due to a high unemployment rate, rural youth commonly opt to pursue employment in cities or carry out agricultural work at home. However, their ability to procure formal employment is hindered by competition due to a high youth population density. This study sought to understand how youth with different levels of formal educational attainment (no schooling, primary schooling, secondary schooling) learn information in their community and formal schooling to improve their livelihoods and develop sustainable practices for generating income. Methods: Through semi-structured qualitative interviews and focus group discussions, the study examines differences between the groups in what they seek to understand and the different pathways they use to learn. Results: Although there were positive effects of schooling among the participants in this study in terms of boosting their self-confidence and self-esteem, youth dropouts with schooling experience overwhelmingly reported that they did not learn approaches and information in their schools that were beneficial for improving their livelihoods. Conclusions: Since the majority of Tanzanian students, and particularly those from rural areas, will be unable to study in higher education institutions, educational programs for youth in school and for school dropouts are more effective which center on methods for learning new information that are applicable to their intended occupation within their community and which also prepare them for participating in the workforce.