Progressive schools, by their very nature, need to respond to changing societal conditions. Within that context, learning guided by the teachings of John Dewey will not only make the progressive tradition sustainable but also make it increasingly relevant in a future that will increasingly make demands on students to possess the knowledge to respond to change effectively and productively. This article provides an introduction of the progressive Hanahau'oli School, which was launched in 1918 when Sophie Judd Cooke and her husband George brought together their six children with friends on a vacant lot at the corner of Makiki and Nohea (Nowewhi, then) Streets. The article also discusses the characteristics of progressive schools and the progressive school in the 21st century.