Starting by complexity, liquidity, fragmentation that, as highlighted in the literature (Sennett, 2008; 2012; Bauman, 2011; 2013), characterize the post-modern condition, underlines the need for the education system to define and propose formative strategies that, by capturing the transition from technical rationality to personal and professional reflexivity, are able to orient individuals in ability to plan the future, being guided by a wider awareness about the prospects, the systems and processes of meaning that compose their life trajectories. Through the pedagogical review of career construction theory (Savickas, 2005) and self-construction theory (Guichard, 2010a; 2010b), actually among the most influential in guidance and both ascribable to the paradigm of Life Designing, the article proposes a reading of guidance processes like processes of reflexive education focused on life trajectories, which try to define possible prospects and borders of this specific aim for research and intervention from an educational point of view