Since the development of the Sustainable Development Goals, extending the number of years of schooling has been widely acknowledged as a way to improve the quality of education regardless of the context. Regarding Madagascar, where the school enrolment ratio is still low, it is important to know how children with little education adapt to such an environment. This study investigates the trajectory of such children in rural areas from school to work and examines the extent to which education succeeds or fails in ensuring they have decent work. Semi-structured interviews were used to collect data over a period of two weeks in February and March 2017. The participants were 6 head teachers, 10 groups of teachers, 9 groups of students, and 3 groups of parents from 6 primary schools, 2 lower secondary schools, and 4 upper secondary schools in the district of Miarinarivo in the Itasy region. The results revealed four major findings: (1) The combination of the high cost of education and growing negative perceptions of its outcomes, coupled with the comparatively strong economic opportunities outside of the school track, deviated the trajectory of children from its initial setting. (2) Children's aspirations change according to their environment. Very little help is given by the school or parents in shaping them. As aspirations grow into concrete plans, difficulties arise, ranging from precarious financial circumstances and parents' lack of motivation to a distrust in the system and society. (3) The austerity of the environment, the absence of career counseling, and the mismatch between education and the social context also prevent children from advancing in education that should lead them to a decent job. Conversely, those who succeed are pulled little by little away from their community at every stage of their education. (4) Those who stay become teachers. Teaching at a primary school remains a decent job that is easy to secure. Up to now, this has fit education budgets; however, the emerging policy of recruiting better-qualified teachers is likely to deprive rural people of this opportunity.