My dissertation focuses on three understudied dimensions of challenges among youth in Malawi, and is structured as three separate papers. The first is, the relationship between aspired and actual timing of transitions out of school, and the extent of the gender gap in this relationship. The second dimension is gender disparity in acquired skills and learning outcomes in primary school, and how demands for labor at the household level help explain differences in dropout and student performance on Math and Chichewa tests. The third dimension focuses on girls’ relationship power, and the gender socialization experiences at school and individual characteristics that are correlated with it. Using the Malawi Schooling and Adolescent Study (MSAS), I find that 1) a higher desired age for marriage is associated with a lower likelihood of school dropout, and marriage related school dropout, with this association significant mainly among girls, 2) a high work burden is associated with a greater likelihood of school dropout in the subsequent year, but is not associated with performance on Math and Chichewa reading comprehension tests, and there is no significant gender difference in these relationships, 3) attitudes form an important dimension of the measurement of girls’ relationship power, and earlier experiences of physical violence in school, and individual characteristics including self-esteem and attitudes against spousal violent predict power in relationships in later adolescence and early adulthood. Together, the three papers in this dissertation provide critical insights into individual mechanisms that allow adolescents to stay in school longer, structural constraints like household labor allocation that limit their educational attainment, and the contribution of early socialization experiences to girls’ power in later relationships.