This chapter addresses the challenges incumbent firms face in transitioning to a circular economy (CE) through the lens of paradox theory. Drawing on a longitudinal qualitative case study of Flokk, a European furniture manufacturer, we explore how incumbents navigate tensions in CE transitions. Flokk experimented with new business models, utilizing recycled materials and product-as-a-service approaches, which required new value chains. We find that Flokk adopts five key strategies: i) business model innovation, ii) engagement in public policy processes, iii) strategic acquisitions, iv) external collaborations, and v) cross-sector R&D partnerships. These strategies foster interactions across sectors through novel forms of collaboration. Our analysis challenges existing typologies by offering a pluralized view of incumbents, highlighting the contradictory yet interrelated aspects in transition processes. Against this backdrop, we argue that paradox theory provides a valuable perspective for understanding the dynamics of CE transitions.