Transitions in the life course are framed by institutional arrangements connected to changing contexts of work and learning. As neo-liberal politics impact on these institutional arrangements, the demand for flexible characters translates into the challenge to manage yoyo-careers, a series of transitions from labour to unemployment to further education and back again. In these spaces of transition, education is expected to serve individuals’ demands for orientation and certainty; tune up skills and meet human resource demands; and care for social continuity and justice . Educational work in these boundary zones of transition is exposed to organisational and ethical re-configurations. The light (of visible institutionalised learning) and shadow (of informal self organised learning) meet and neo-liberal imperatives turn the light away from educational work towards the demands of employability. This paper examines educational work in zones of transition. Using secondary analysis of further education surveys and policy papers I elaborate the discourse redesigning educational work as managing life course transitions and biographies. Qualitative data from a collection of worklife histories of educational staff working to support transitions between work and learning provides evidence showing how professionals deal with ethical conflicts and dilemmas in these processes and how they see educational work.