The perceived, lived and planned future represents one of the main pedagogical categories that needs to be analyzed in the context of social representations and guidance itineraries that lead individuals to project themselves into an imagined time. Compared to the past, the lack of linearity in existential paths prevents us from establishing a precise taxonomy of choice processes that, taking place outside of consolidated schemes, require more complex and critical challenges, such as that of the continuous and incessant redefinition of identity. In this regard, it may be useful to recall the construct of problematicity to remember that it is configured as that given condition of being in the world, characterized by characteristics that are partly the result of the individual’s choices, partly connected to the pre-established context. Orienting oneself to the future means proceeding according to an existential protagonism, that is, engaging responsibly in a laborious project of transformation of the initial condition. In this framework, the future is to be understood as a social question and a precise educational responsibility, which at the same time presents itself as a question that awaits individual, subjective and unique answers. The article proposes a reflection on guidance processes for the future and intertwines the categories of freedom and creativity, as aspects that qualify its nature.