This transnational review begins with the importance of transcultural cross-fertilizations between three hitherto seemingly disparate cultures and the education experiments which arose in each of them: India, Denmark, and the United States. The great Odisha philosopher and educator Chitta Ranjan Das’s education began in Rabindranath Tagore’s Shantiniketan, a similar context to the Danish Folk School, and he continued his work in Gandhian Ashrams. The origins and social impacts of the Danish Folk High School provided a model of creative transformative education, which had come to the United States with Myles Horton and the historical and societal contribution of the Highlander Folk School to the American Civil Rights Movement (1930s–1960s). Likewise, Chitta Ranjan Das had studied in Denmark, Vienna, and elsewhere in Europe. Parallel to this development were Highlander Folk School and other folk schools in the United States, as well as the work of Paulo Freire, Myles Horton, and others. At the end of the twentieth century and the beginning of the twenty-first century, we have witnessed a continuation and expansion of the multiple strands and legacies of these great educators through the surprising, explosive growth of Folk Schools. Self-realization and societal reform are concerns of current Folk Schools as they were for Chitta Ranjan Das. His work and contributions help us understand the similarity of these deep spiritual and creative contributions made in parallel during the twentieth century across the globe and how their impacts on the twenty-first century are emerging. We include here an account of the recent evolution of Folk Schools in North America (1990–2024) and their contributions to transformative leadership in local communities of practice (COP). We then discuss how the thinking and works of Chitta Ranjan Das, the great Odia Philosopher and integral educator, reflect and intersect with those of Highlander and contemporary Folk Schools. Anticipating Arturo Escobar and the ‘pluriverse,’ the ‘waves and currents’ of these movements across the world lead to realizations of an emerging planetary education for liberation in what can be seen as ‘schools for life.’