In the course towards the knowledge society, work practices (teaching, learning, educating) and the educating/teaching professions are being re-configured relative to education-work, state-economy, school-companies. My presentation will illustrate how these relational tensions are embedded in discourse on education, affect institutional arrangements and influence professional agency of teachers, trainers and other educational staff in vocational as well as in general education. It offers a conceptualisation of educational work in terms of ‘transition’. Transition research moves issues of space and time to our focus by relating institutional and biographical dimensions of transition. It opens a window for the analysis of theoretical explanations, policy strategies and agency of professional educators in negotiating the differing interests and logics of education and work. I develop this argument historically. I contextualise my case by examining the discourse of negotiating education and training in Germany since the times of Kerschensteiner. I then draw on career histories of education workers from differing institutional settings to consider how professional educators – teachers, trainers, social/youth workers, coaches, counsellors, etc. – make sense of the tensions between education and work and how their professional activities contribute to the reconfiguration of this dilemma driven relationship as lived experiences and enacted practice of educational work.