Ukraine will face unique challenges if and when the Russian invasion has ended. The transition from wartime to peacetime can result in many social and political outcomes. The possibility of a persistent threat adds to the complexity. The transition from the more autocratic needs of wartime society to a nonmilitaristic democracy is by no means guaranteed. Lessons can be learned from past experiences, such as post-WWI and -WWII Germany, and the failed reconstruction of the Civil War in the United States. Social scientist Kurt Lewin (1890–1947) provides a theoretical basis for contrasting democracy and autocracy. Lewin applied his theories to understanding the failure of democracy in post-WWI Germany and the reconstruction of Germany after WWII. Using Lewin’s work as a foundation, this article considers lessons learned in hopes of being a guide for the eventual cultural reconstruction needed in postwar Ukraine.