Humans are at the center of global climate change: The United Nations Sustainable Development Goals (SDGs) are igniting sustainability with proactive, global, social goals, moving us away from the Brundtland paradigm ‘do nothing today to compromise tomorrows generation’. This promotes a regenerative shift in the sustainability concept, no longer only considering resources and energy, but also significant human-centric attributes. Despite this, precise ecological and sustainable attitudes have little prognostic value regarding final related individual human behavior. The global cultural challenge, dominated by technological innovations and business imperatives, alongside the mirroring technological fallacy and lack of ethical reasoning, makes the role of small actions, at individual and at academic scale even harder. This paper outlines the context in which universities can collaborate and contribute to triggering sustainability values, attitudes, and behavior within future regenerative societies. This contribution consists in three main areas: the first analyzes the issue of sustainability transitions at the individual scale, where influencing factors and value–behavior links are presented as reviewed from a number of multi and transdisciplinary scholars’ works. The second part enlarges the picture to the global dimension, tracing the ideological steps of our current environmental crisis, from the differences in prevailing western and eastern values, tradition, and perspectives, to the technological fallacy and the power of the narratives of changes. Finally, the task of our role as academics in the emerging ‘integrative humanities’ science is outlined with education promoted as an essential driver in moving from sustainability to regenerative paradigms.