Most recent data on international migration trends indicates that the net emigration rate from Estonia is the highest in the European Union. At the same time, an increase in return migration of compatriots has become a goal that various national institutions work towards. However, research on post-socialist migration reveals little on the longer term trends in mobility. I aim to start filling this gap in our understanding of the temporal dimension of migration and its triggers by the following twofold research. Firstly, I aim to map the variations over the course of migratory careers of transnational Estonians. Secondly, I will apply theories of governmentality to the study of the interplay between the agency of migrants and the institutional and associational context structuring migrants’ careers. Focussing on migration between Estonia and the United Kingdom, I will employ quantitative and qualitative methods to pursue the following research questions: how do national institutions (including funding programmes and initiatives) reach across borders to “recapture” migrants to govern them in the direction beneficial for the sending country? What interactions does this generate with diaspora organisations and migrants’ networks? What role does this structural environment play in migrants’ careers in terms of the direction and type of mobility (settling into the new country, returning home, oscillating, or becoming a serial migrant)? This study will generate a novel synthesis of research which advances both the anthropological theories of transmigration and power as well as the methods in migration research. As such, the project has implications for policy-making as the meanings of and motivations for mobility play a vital part in understanding the potential of institutional interventions. Intended as the baseline study for the future longitudinal research into migratory careers, it is also expected to advance the interpretation of available data on migration trends.