This article relies on court, church, and manor archives along with memoirs and the press to explore the aspirations of social climbers of peasant origin to become manor administrators and tenant proprietors in Southern Estonia in the 1860s to 1880s. The article draws on information concerning a total of more than fifty manor administrators and tenant proprietors who were born between 1804 and 1869. The article’s first part examines the kinds of environments that manor administrators and tenant proprietors grew up in and how they got their chance at the manor. Thereafter the article explores how they coped with their responsibilities and tasks, and the kinds of difficulties that they encountered. Finally, life is described from their vantage point while at the same time striving to understand what the status in the eyes of locals was of compatriots who had rented and administered manors.

The contingent of manor administrators, as well as that of tenant proprietors, was exceedingly varied in terms of their skills, education, preparation, and wealth. It became possible to rise to the top of such a diverse contingent because the manor economy had been modernised very unevenly throughout Estonia. Manor holdings differed in terms of their size, location, and economic potential, as well as the expectations and needs of their owners. Since a shortage prevailed of qualified agricultural administrators, it was not exceptional for an uneducated country boy to get his chance. If he was fired from the position of manor administrator due to his insufficient skills, differences in opinion, loss of trust, or some other reason, it was quite easy to find a new job. Very few administrators of peasant origin stood out as improvers of agriculture. Bookkeeping and work supervision were the jobs usually left to social climbers of peasant stock.

Tenant proprietors of Estonian origin displayed more boldness and courage for taking risks than knowledge of how to manage manors sustainably. Sooner or later, those who were unable to implement capital-intensive innovations and instead pinned their hopes for staying afloat on renting out the existing infrastructure, or on taking out ever more new loans, had to terminate their manor rental agreements. Generally speaking, doing business in trade and speculation was considerably more agreeable for social climbers of peasant stock and more within their powers than redesigning and developing the administration of manors. Alongside success stories, at least as many utter failures were found among tenant proprietors.

An affectedly refined lifestyle characterised manor administrators and tenant proprietors: they generally belonged to German congregations, married women from ‘better strata’, Germanised their names if possible, schooled their sons in the towns to become white collar employees, and they themselves eluded participation in building nationalist Estonian society. Many swindlers and bankruptcy artists even helped their sons to respectable occupations in towns by providing them with quality education. Yet this contingent of social climbers was still very closely connected to country folk, both occupationally and through credit relations. Regardless of how hard they tried to sever ties with their peasant background, many of them did not manage to rid themselves from traits attributed to country bumpkins, like violent behaviour, carousing in pubs, or vulgar usage in speech, for instance.