This article explores the nexus between life (dis)satisfaction, migration aspirations and return and development within the context of a previously relatively developed but in the meantime deprived post-Soviet country, Ukraine. It is based on a mixed method quantitative and qualitative study conducted from 2010 to 2013. Three key findings have been emerging. First, life dissatisfaction significantly contributes to the emergence of migration aspirations and thus is an important driver of migration. This points to a correlation between the state of development of a country, according life (dis)satisfaction of its populations' and their propensity to migrate. Second, the study suggests that the better educated have stronger intentions to migrate abroad; this trend rather undermines the country's capability to develop further. And third, our findings suggest that (a) expected dissatisfaction with life in Ukraine upon return undermines migrants' aspirations to return or to stay and instead inspires remigration and (b) that those who return have little incentive to invest skills and capital and thereby contribute to the country's development. This raises various policy concerns for so far absent diaspora politics or reintegration measures which we will discuss.