This study investigates the paradoxical influence of family income on school dropout risks among Brazilian public-school students. Discussing previous results that challenges traditional perspectives on school dropout by examining how students from higher family income show higher dropout risk. We hypothesize that this is due to flexible capitalism changes in our societies labor market and to the devaluation of schools as a meaningful place for student’s life projects. Analyzing data from 15,924 Brazilian high school and middle school students using Multivariate Analysis of Variance (MANOVA) and univariate models, the study reveals that students from higher-income families are more likely to drop out when they perceive school as less relevant for their future careers. This unexpected finding suggests that, unlike most literature on this field, higher income students might be at greater risk of dropout due to the pressure to enter the workforce and the perceived lack of school's alignment with their career aspirations. This study contributes to the understanding of school dropout in the global south, proposing the need for educational reforms that align with contemporary labor market realities.