This study details the research of three organizations from the perspectives of complexity science and communities of practice. We conducted in-depth interviews with key leaders from three organizations: an organization for nursing leaders, a spiritual and self-development practice of the Jewish faith called Mussar, and an urban co-housing community. Meaningful connections between the interviewees’ stories and 12 comprehensive elements of complex adaptive entities are discussed. From these findings, a relevant similarity dealing with community, specifically communities of practice, emerges, and we subsequently identify key elements of communities of practice among the three entities. The paper concludes with lessons from our research to date as well as recommendations for future research.