This article provides ethnographic insights into the Southeast Asian peasantry’s engagements with agrarian change. It speaks both to Southeast Asian studies’ longstanding interest in the dynamics of socio‐economic transformation, and to anthropology’s burgeoning focus on how future‐oriented aspirations are produced, negotiated and enacted under specific socio‐political, material and historical conditions. Drawing on 12 months of ethnographic fieldwork in an ethnic Khmu hamlet in northern Laos, I show upland peasants on the cusp of agrarian transition engaging aspirational migration through ‘controlled experiments’: pioneering pursuits of betterment, crucially buttressed by multiple, locally specific factors. These factors include a still largely intact peasant natural economy, historically endowed intimacy with the modernising state and, not least, a precariously persistent ‘intergenerational contract’ in which youthful mobility and parental stability remain ambiguously yet irreducibly intertwined. Notably, whereas much research on Laos has focused on communities (adversely) impacted by transition, this article discusses a community that is both politically connected and, concomitantly, still relatively unscathed by the (transitory) detriments of commodification, enclosure and dispossession. In sum, this article confirms that while striving for a better future is probably a basic aspect of the human condition, definitions and pursuits of such futures are contextually contingent, not least along generational lines.