Highly skilled migrants and expatriates are the subject of the global
competition for talent. Their human capital is considered as positive,
and it is expected to be wanted and not brain-wasted. Economic benefits
and career building represent acknowledged reasons for migration of this
“elite”. Their decision-making on migration is a complicated and
multi-layered process, which is not limited to the interests of the
individual, the receiving country, or the corporations. Instead, highly
skilled migrants living in a global diaspora or in a transnational
space, negotiate their migratory options beyond their career sphere.
Therefore, the dynamics of the migratory life of self-initiated
expatriates require a better understanding, further theorizing and novel
propositions addressing their embeddedness and contextuality. Hence, we
examine life trajectories over time and analyse how specific episodes
and proximity to family shape the decision-making of male self-initiated
expatriates (SIE). SIEs moving to Finland provide evidence
contradicting previous views on the role of post-migratory gains in
decision-making and highlight complex employment-entrepreneurship
outcomes. The study contributes to self-initiated expatriation and
transnational diaspora studies.