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.G8WAY is based on the idea, that the growing availability of web 2.0 allows for bridging this gap through learner centred and connective approaches, with a chance to more effectively manage educational transition. Thus, G8WAY will develop web 2.0 enhanced learning environments, which will enable learners to reflect and develop creativity potentials and transitional skills in the light of self and others' learning experience, made visible through a variety of media sets and PLE tools, each of them designed to meet the requirements of transition envisaged, and all of which are mapped into one single pedagogy framework.G8WAY will produce 2 transition scenarios, which is a) school to work and b) general to higher education. A third scenario will test the latter ones in an intergenerational learning setting. For each of the scenarios a problem oriented concept and case based reasoning method will be developed and embedded into a web 2.0 learning environment. The project capitalizes on the outcomes of excellent EU projects, which developed e-tools to make visible informal competencies through media such as digital video and fotography, digital cartoons, assessment tools and e-portfolio.