The Circular Economy is gaining traction in the European Union and all over the world as a transition away from the extractive and exploitative linear economy. In Hawaiʻi, the cultural value of aloha ʻāina is a philosophy describing a set of values grounded in a relationship of kinship between people and the environment. Aloha ʻĀina structured centuries of sustainability and it has evolved over generations to frame community responses to crucial issues today, such as climate change, oligopolistic markets, and contemporary land management. This paper sits at the intersection of cross-disciplinary collaboration, sustainability, and sustainable development. Participative moderate observations and intentional cross-cultural exchanges of knowledge over five years between scholars and experts in the major fields of indigenous Hawaiian knowledge and industrial ecology inspired the concepts explored in this paper, which address the question of how aloha ʻāina and the Circular Economy can engage with each other in the collective effort to combat climate change, guide sustainable development efforts, and transition societies toward sustainability. Extensive literature reviews and insight gained through site visits to sustainability projects inform the discussion of best practices from opposite parts of the globe—Hawaiʻi and Germany—to put into conversation two worldviews and present resulting implications and lessons learned. Essential findings describe the benefits of knowledge exchange between members of global practitioner networks. By shifting expert and participant roles according to which projects are being observed, cross-cultural characteristics can be explored at a deeper level, which allow participants to employ best practices to their respective theories. The Circular Economy’s engagement with indigenous knowledge systems is an opportunity to ally and produce solutions to the challenges associated with changing the linear economy while addressing both environmental and social justice issues.