Ki Hadjar Dewantara was an early advocate of independence from the Dutch colonial rule in Indonesia. The goal of independence from colonial rule was widespread in his day in the Dutch Indies and elsewhere. Dewantara took the issue, not just as a goal, but also as a question. What should independence be for Indonesia? Working with many other people, a series of answers emerged to this question over time and played a critical role in imagining the new nation of Indonesia. An important articulation of the emerging answers was the Taman Siswa schools, which drew from the ideas of Montessori, Froebel, and Tagore, adapted to the Indonesian colonial context. This case builds on understanding of social and material interactions in creative work, considered in previous cases, and highlights the role central questions can play in the organization of creative work. The discussion also juxtaposes Mao’s conception of his revolutionary work as destroying the old to make way for the new (Chapter 5) to Dewantara’s use of the past to bridge to the future – the walking backward metaphor from improvisational theory. Full case analysis presented in Creativity and Improvised Educations: Case Studies for Understanding Impact and Implications.