This paper studies the economic consequences of conflicts between timing institutions, the rules that govern when schooling, work, and other activities take place, and local economic conditions. We focus on the overlap between school calendars and local agricultural cycles, and document systematic misalignment between the two across countries in southern latitudes. These patterns reflect institutional legacies, as inherited institutions continue to shape the design of school calendars in previously colonized countries. Exploiting this colonial variation as an instrument, our cross-country estimates indicate that greater overlap between school terms and agricultural labor demand increases school dropout rates. To identify the underlying mechanism, we use school-level data to study a calendar reform in Colombia that exogenously increased overlap in two departments. Using a synthetic difference-in-differences approach, we find that calendar misalignment induces a trade-off between schooling and labor, resulting in higher dropout and lower enrollment in rural areas. Our findings highlight the importance of timing institutions as a determinant of human capital accumulation and suggest that aligning social institutions with local economic conditions can generate substantial gains for economic development.