Azorean migrant workers returned to their archipelago and became self-employed in their country of origin. Based on exploratory fieldwork, this chapter explains how former employees decided to become self-employed upon their return to Portugal. To answer a how question, a qualitative approach was used. Interviews, conducted in the Azorean archipelago, and in the main destinations of Azorean migration—Canada and United States—reveal that emigrants seldom left the Azores with the intention to return. However, while abroad, Azoreans socialised with sojourners from mainland Portugal who spoke of their intention to return. Having accumulated savings from their sojourn, many Azoreans returned home. Self-employment after their return migration is neither growth-oriented nor technology-based; rather, their self-employment is a means to have an occupation that brings pleasure, while maintaining financial assets.