The medieval approach to work was ambivalent, influenced by conflicting cultural legacies, as seen in the tripartite society and tensions between labour and ascetic ideals. The text explores medieval labour contracts, emphasising nuanced relations between servitude, subordination, and freedom, both in rural and urban context, highlighting evolving worker statuses in guilds. Medieval views on mechanical arts challenged Greco-Roman disdain, with intellectuals reconciling manual arts with divine wisdom, reshaping perceptions of practical skills. Societal changes, including city growth and merchant inclusion, challenged traditional orders: a new human perspective shaped by cities, merchants, rationality, and time, paved the way for ‘new man’ of the Renaissance.