PhD graduates are dealing with a lack of opportunities regarding long-term careers: the chances of eventually obtaining a stable position in university are hardly higher than a few per cent and slimmer when geographical constraints are set. The current scenario prospects a panoply of professional destinations for PhD graduates beyond university walls, but the doctoral education system is still primarily designed as a preparatory phase for an academic career and academic employment remains the preferred option for the majority. The concrete risks of this situation are connected to over-skilling, lack of recognition and problems in transferring skills during transitions from university to other workplaces. The article focuses on one underestimated dimension of these processes: the tacit knowledge implicitly acquired in HE institutions and structuring a peculiar 'academic habitus' which plays a crucial role in terms of unexpected difficulties as well as unexplored learning potential. Doctoral training may represent a strategic place where students can begin to interpret the complex issues involved in transition processes not as signs of inadequacy or lack of preparation, but as challenges engaging one's agency in dealing with a different organisational habitus. Individual strategies are, in fact, essential in making a difference when a disorienting dilemma emerges and they configure a proper meta-competence to be developed and fostered. More broadly the article argues that, in order to sustain the potential of PhD graduates' knowledge it is necessary to overcome a reductionist and instructional perspective in approaching learning outcomes.