Japanese life and career situation have become opaque due to nationwide problems such as the collapse of lifetime employment, the aging society with declining birth rates, and the drop in GDP manifested in a reduction in international competitiveness. Statistics show that the younger generation of Japan has significantly lower ratings of self-confidence, willingness to contribute to society, and hopes for the future, compared to other nations. Under these circumstances, we aimed to speculate on a humane vision where everyone can live with a meaningful purpose (* ikigai* in Japanese) from the historical city of Kyoto, Japan. Using the theories underpinning Transition Design, this paper reports a case study on the core four activities of Transition Design. We introduce the tools and processes rooted in local culture and history. Then we show a design fiction that conveys place-based and decentralized future visions inspired by Japanese traditional Arts. Finally, after practicing the first Transition Design project in Japan, we reflect on the designer’s mindset to address Wicked Problems of the 21st century from the perspective of Pluriversal Design, which discusses epistemologies and methods of design researchers from outside of Europe and North America.