This paper uses linked apprenticeship-family reconstitution records to explore the influence of family structure on human capital formation in preindustrial England. We observe a small but significant relationship between birth order, resources and human capital investments. Among the gentry, eldest sons were almost never apprenticed. Outside the gentry, a large number of apprentices were eldest sons, even from farming families. This implies a relatively large place for a child’s aptitude and interest in shaping their career compared to custom or inheritance practices, making the “middling sorts” behave much more as families do in present-day labour studies than the contemporary elites. We also find a surprisingly high rate of return migration, questioning the emphasis on neo-locality and suggesting that parents could anticipate benefiting directly from positive externalities arising from the training provided to children. This interpretation also fits well with our finding that if parents had died before indenture, apprentices were significantly less likely to return home.