A major characteristic of European societies might be seen in the rapidly growing differentiation of educational pathways, opportunities and biographies. This increase in complexity from learners requires great effort into initiative taking, creativity, problem solving, risk assessment and decision taking. Through the past years various structures have been developed in order to support students in mastering educational transition. However they have been often formulated in an institutional perspective, counting out learners' experience and creativity skills as well as new opportunities of technology enhanced learning.