Smallholder farmers remain central to rural economies across developing countries, yet small landholdings and limited non-farm opportunities constrain their ability to achieve a living income. Using harmonized household survey data from 37 countries and panel data from Ethiopia, Nigeria, the United Republic of Tanzania, and Uganda, this paper examines the link between farm size, livelihood strategies, and income. Results show strong regional contrasts: in sub-Saharan Africa, larger farms are associated with agricultural income specialization, while in South Asia and other regions, even larger farmers diversify more into off-farm activities. Fractional response and correlated random effects models confirm that land size drives agricultural specialization where rural labour markets are underdeveloped but has limited influence on non-agricultural income shares. As access to education and urban employment improves, the importance of land size declines, underscoring the need for policies that complement agricultural investments with support for rural education, infrastructure, and non-farm job creation.