From the 1930s through the present day, many of the elected and appointed members of Transjordan and Jordan’s Legislative Council and National Assembly were formerly teachers in the schools of the British Mandates of Palestine and Transjordan. A combination of factors promoted the links between teaching and political office. A scarcity of educated persons meant that almost anyone possessing a secondary school certificate, and certainly a university degree, could quickly find employment in the Government Departments of Education. Moreover, those employed in these Departments of Education could not easily be replaced. Therefore poets, journalists, pedagogues and activists frequently used teaching as a way of subsidizing their political activities. Teachers also enjoyed a captive audience of the Mandates’ most impressionable inhabitants; children. Educators used their experiences as leaders in the classroom and as negotiators with government bureaucracies, to bolster careers not only in education but in politics, journalism, literature, as well as academia. This paper examines how the interactions between teachers and the British Mandate Governments of Palestine and Transjordan shaped these individuals’ dealings with the state more generally, by using reports and memoranda from the Departments of Education, teachers’ personnel files, memoirs, colonial and foreign office documents as well as interviews with former students and administrators. Analyzing Palestinians and Jordanians whose careers began in the schools of the Mandates and ended in the Government of Jordan provides a window not only into practical connections between schooling and governance in a colonial context but also into how concepts of authority based on negotiation and a flexible, if frequently impotent notion of governance are understood and adapted.