To respond to structural challenges that school is confronted to today, two paradigms are opposed. One aiming for improvement (Bryk, 2015) and the other for transformation (Engeström, 2017) of education systems. This second goal, supported by cultural historical activity theory (Engeström, 1987), calls for an advanced form of learning, expansive learning (Engeström, 2001), that leads to transformation through the untangling and surpassing of contradictions, that have been deeply rooted within the education systems. This article, like a narrative review, explores the potential power of transformation through expansive learning to evaluate its feasibility in context. We achieve this by brushing a complete picture of expansive learning, including its foundational theories, we then contextualize the concept through real examples of its application. This process resolves in a nuanced conclusion, which goes beyond the spectrum between realism and utopia, all the while straying away from idealism, that affirms that the application of expansive learning will face immense challenges but is a necessary process for the future of schools and their survival in the face of the multiple landslides shaking their foundations.