Whereas migration research has been heavily influenced by the individualization paradigm, studies on return migration have been more inspired by theories on attachment and belonging. It is common for this kind of research to assert that the main motivations for returning are social contacts and a homing desire. Although this article does not question the importance of such motivations for some, it does argue that return migration needs to be more problematized, not least by studying people who have decided not to return. Based on interviews with highly skilled Estonians, this article suggests that return decisions are influenced by three types of comparisons: social, temporal, and intra-subjective. The first two comparisons have been discussed to some degree in migration literature; however, a focus on intra-subjective comparisons – in which people compare different parts of their identity in order to decide on a potential return – has been scarce. This article suggests that, in line with the individualization of social relationships, but also with the introduction of a new EU mobility space, it is the latter type of comparison that is becoming increasingly widespread.