Learning from the experience of leading designers is invaluable in accelerating the transition to a circular built environment. This research, therefore, aims to conduct an interpretative phenomenological analysis (IPA) of circular design experiences. IPA is a relatively recent, yet increasingly popular, phenomenological approach to examine how people experience a particular phenomenon. Unstructured interviews with ten frontrunning designers comprise our primary source of data. We asked each participant a single, open-ended question – “could you please tell us about your experiences with circular design?” – and then probed to let them run with it. The interviews were all recorded and transcribed verbatim. For the analysis, we employed IPA’s flexible guidelines to iterate between the three steps of: multiple reading and making notes; transforming notes into emergent themes; and seeking relationships and clustering themes. Our interpretative phenomenological analysis has, accordingly, resulted in four themes that illustrate how designers make sense of their own circular design experiences: proclaiming responsibility towards the environment; materializing future-oriented solutions; dealing with a multi-headed monster; and orchestrating an ecosystem. These four themes reflect what it is like to engage in circular design. Other researchers and practitioners can learn from the experiences of pioneers to make better decisions and prepare for challenges in navigating the circularity transition.