Investigating entrepreneurship complexity in multiple contexts, perspectives and approaches give rise to multiple perspectives of collective entrepreneurship. However, current understanding of how multiple self-employed individuals undertake collective entrepreneurship is poor. Our study investigates four collective entrepreneurial journeys taken by self-employed healthcare practitioners; these journeys lead to the creation of four rural PCCs in southwest France and southwest Germany. Our study extends understanding of the unfolding of engaging for collectiveness among self-employed individuals. Our interpretative and practice-inspired approach identifies regional embeddedness and peer co-working as being interconnected enablers of collective entrepreneurship in rural areas, and we reveal conflict between professional practitioner ethos and changing work culture. We improve how we understand the creative organizing of self-employed individuals by (i) theorizing well-being as a driver of collective entrepreneurship in the rural healthcare context; (ii) conceptualizing regional embeddedness as a process of ‘being in, ‘doing at’, and ‘understanding of’ the territory; (iii) conceptualizing peer co-working as a practice that involves sharing a workplace, developing skills, and benefitting from social interaction; and (iv) theorizing peer co-working as a catalyst of collective entrepreneurship. In summary, we theorize regional embeddedness and peer co-working as being interconnected enablers of collective entrepreneurship in the pursuit of well-being.