The shift from a linear economy to a circular bioeconomy comes with many challenges in culture, behavior, business, technology and institutions, requiring transformative change. Circular initiatives are considered starting points for such a transformation as they demonstrate tangible alternatives to a linear, fossil-based economy. However, detailed insights into the progress of circular impact made by these initiatives have been lacking. Furthermore, conceptualizations of their development have primarily focused on upscaling, neglecting the diverse and dynamic development trajectories these initiatives might take in practice. The research aim of this paper was to better understand how circular initiatives contribute to transformative change. This study empirically explored three different development trajectories of circular initiatives; deepening (become more radical and circular), broadening (connecting with other domains and agendas) and spreading (becoming larger and more numerous). Based on interviews and desk research, 31 circular initiatives in the Netherlands were studied– in the domains of agriculture, biobased materials, marine research, and nature. The results revealed eight configurations, which are combinations of mechanisms that together guided initiatives’ development: deepening of initiatives was triggered by 1) focus and 2) reorganization: broadening was driven by 3) unusual collaboration, 4) aligning interests and 5) establishing a focus; and spreading occurred through 6) increasing capacity, 7) credibility and 8) offering perspective. These eight configurations provided in-depth insights into the diverse and dynamic development of circular initiatives. The configurations highlighted the significance of the interplay of mechanisms in studying the development of initiatives and in designing strategies to guide current and future circular initiatives.