Land change science has demonstrated that rural livelihoods around the world both drive and reflect changing environmental regimes and political economic/structural transformations. This article explores the relationship between increasingly globalized rural livelihoods and in-place land change, assessing results from social surveys of smallholding households in the southern Yucatán region. We examine evidence for a transition in agricultural livelihood strategies as smallholders adjust to changing political economic and institutional conditions, and link these transitioning strategies to land use changes. Based on household surveys in 1997 and 2003, we comparatively assess both changes in the selection of livelihood strategies and in the land use and cover impacts of those strategies. Our results indicate that although impacts of given strategies have changed little over this period, there are increasing proportions of households pursuing two divergent adjustment paths—one of agricultural withdrawal and one of agricultural intensification and commercialization. We investigate what sociodemographic characteristics differentiate the groups of households following distinct livelihood strategies. Our findings point to the possibility of simultaneous and contradictory land change outcomes as smallholders adjust in different ways to their intensified incorporation into global economies.