The nature of work with and for humans and communities requires intentional relationship building that can be rife with complexities, foibles, discomfort, and learning. As scholars, researchers, practitioners, educators, and students, we carry a multitude of identities and dispositions that make collaborative work and change-making a messy and potentially emotional journey. Thus, many groups that find themselves on this journey often struggle to develop harmonious or impactful lasting relationships and often create toxic or harmful working environments for those who are the most marginalized or have the least power. The goal of this work is to provide a reflection on a specific instance of collaborative work and the associated journey in order to provide recommendations for more thoughtful, people-centered engagement. Hopefully, this reflection inspires those of us who work collaboratively to design experiences and artifacts in a way that marginalizes less and emerges more. In this light, we can co-create solutions and interventions with the very people we seek to serve.