This article compares the geographic and social mobility of two “lesser known” groups of workers: merchants’ assistants and maidservants. By combining labor mobility, class, and gender as categories of analysis, it suggests that such examples of temporary and return migration opened up new economic possibilities while at the same time reinforcing patriarchal order and increasing social inequality. Such transformative social practice is placed within the broader socio-economic and political fabric of the late Ottoman and post-Ottoman Balkans during the “long 19th century.”