The relationship between users and learning environments can be seen as an ecology. Attending school is not only about teaching and learning but is also about growing human beings. While social learning helps shape personality, relating to others and being better citizens, these social dimensions are often underestimated and forgotten under pressures of final grades and curriculum delivery. More than schools, we need learning organisations to equip students with knowledge and skills necessary to succeed in an uncertain and constantly changing environment, bringing the learning community together for a better and enhanced learning experience. This chapter investigates the key role design research can play in this flourishing process and re-imagining schools as part of a wide ecosystem that enables innovative pedagogies and practices. By bringing school communities, industry, policymakers, designers, and researchers together, design research can manage expectations and promote an aspirational dialogue towards better future learning environments.