This study explores the role of John Dewey’s educational philosophy before and after World War I. Before World War I, Dewey’s educational philosophy emphasized individualized and socialized development for learners, importance of children’s education, and encouragement of diverse and creative educational measures. Although these views did not change significantly after World War I, Dewey reflected on the connection between education and social life to allow teachers to fulfill their social responsibilities and to integrate various social issues into teaching regimes to inspire children and create a habit of exploring experience. This study concludes that a democratic education allows children to participate in the problem–solving process, that continuous use of real social issues enhances democratic literacy for children, and that the quality of children’s education depends on teachers’ commitment to social responsibility.