Through design, creative practitioners are able to engage and re-vision full systems which produced them— they are able to think about resource extraction, exploitative labour practices, methods of manufacture, global transport chains, marketing narratives, conditions of use, methods of disposal, and materials’ afterlife (Pfeiffer, 2024). Through specific case studies ranging from ecomaterials to regenerative agriculture and services, this paper will highlight how they are both context and content for each other: how systems create the design’s material and relational qualities, and how the object’s qualities define the systems’ relations and outcomes. We will showcase pioneering examples of those aspirations, design interventions and the impact they have through regenerative design principles in connection to the way they engage in thoughtful ways of thinking, caring, relating, and making. This paper also examines the critical role of design institutions in fostering regenerative practices. These institutions provide an environment of unbounded imagination, interdisciplinary, and openness —spaces that are both provocative and exploratory by design. They enable diverse connections, drawing on a wide range of references, including low-tech solutions and Indigenous knowledge systems. We argue that their unique potential lies, in part, in the (relative) absence of conceptual and practical constraints that often inhibit alternative ways of thinking and making. Importantly, this needs to be connected with a curriculum based on a regenerative worldview which treats humans and the environment as fundamentally interrelated. This argument will be further supported by conversations with creative regenerative practitioners and academics actively working at the intersection of design and ecological practices. Finally, we trace how regenerative ideas evolve as they move from educational institutions to market contexts. Regenerative innovators oscillate between different ways of working as they act as designers, technical developers, and entrepreneurs. These roles carry their own priorities and reward mechanisms. For instance, design as a modality prizes originality, functionality and aesthetics. It encourages risk-taking and individual authorship. In contrast, the technical or scientific mode is rooted in precision, replicability, and feasibility. Meanwhile, an entrepreneurial modality is driven by market fit, scalability, and navigating economic constraints—what works as a design project in an art school is very different when it becomes a venture and an economic system far from being regenerative. The paper will explore how in the regenerative entrepreneurial journey designers navigate competing logics and value systems, which often create tensions and lead to difficult decisions and compromises—as economic choices are sometimes at odds with ecological integrity, idealistic design visions or technically superior solutions. As one of the case studies CEO noted “the activation energy needed to get over that initial development hump is the issue”. Our research identifies value-led design clashes that emanate from current economic system(s) and entrepreneurial templates to critically consider present issues and constraints to cast forward into better possible supportive landscapes. In doing so, we aim to contribute to theoretical understandings of regeneration while offering actionable insights for practitioners navigating the complexities of regenerative transitions. The overarching goal is to generate critical knowledge that supports both scholars and practitioners committed to transformative systems change. REFERENCES Fantini van Ditmar, D., and Toivonen, T. 2025. “Cultivating a Regenerative Imagination at Art and Design Universities.” In RSD13: Proceedings of the 13th Relating Systems Thinking and Design Symposium. Pfeiffer, K. 2024. “Seeing ‘the Object as World-Maker’: Prefigurative Materiality, Biodesign, and the Limits of Material Hope.” Etnofoor 36 (2): 91–108.