Adopting a circular economy approach requires new business models, multi-stakeholder engagement, and tailored financial models and mechanisms as core pillars. This paper examines the conditions needed to scale circular economy initiatives in Europe by analysing insights collected from the DECISO project and conducting a comparative analysis of 38 European projects. The study adopts a mixed methods approach that integrates an online stakeholder survey with inputs generated through participatory workshops and discussions of selected use cases. This combined approach is used to identify the main structural barriers limiting the maturity and investment readiness of circular economy projects, such as regulatory complexity, difficulties in accessing funding, and weak stakeholder dialogue mechanisms. The approach was also used for enabling factors that can support development of circular economy. Particular attention is given to the role of project development assistance, modular financing strategies, and de-risking tools, which are highlighted as crucial elements for supporting the technical and economic credibility of projects and attracting public and private investors. The article also identifies and addresses seven unresolved research gaps in the literature, including the lack of interoperable policy instruments, the absence of business models capable of integrating investor expectations, the paucity of integrated methodologies for assessing technical and economic regulatory feasibility, and the need for trust-building procedures. The findings suggest that the transition to a regenerative economy requires a systemic approach based on coherent policies, de-risking financial instruments, collaborative governance, and strategic technical support throughout the project development cycle.