This gathering signaled the beginning of our four-year exploration into changing municipal service systems to prevent youth outsiderness. The event brought together youth, service providers, leaders, community organizers, and researchers to explore experiences of insiderness and outsiderness and build a foundation for joint action. At my table, we discussed the need for fluidity and porousness in moving inside and outside of different social spheres. One youth highlighted that being outside of the mainstream isn’t inherently bad and sometimes needs to be supported. We talked about the ways that one can be perceived as inside and still feel deeply outside. Across various system actors, we shared our lived experiences of navigating the tensions of belonging and othering in society. The goal of preventing youth outsiderness was, thus, muddled right from the beginning. We frame this work as a collective inquiry because we don’t see it as a straightforward project with pre-determined outcomes to be executed by a few people. Instead, the transformation that we seek within youth municipal service systems is contested, made up of many interdependent issues and largely unknown. We need to learn from each other—the broad array of folks that are influencing and influenced by these service systems—and through experimental action together to explore the systemic consequences of possible changes. There seemed to me to be a readiness in the room. A hunger for doing things differently. A sense of shared commitment to action. But occasionally, the status quo, with its great inertia, also pulled us in when we started to repeat typical system speak and service jargon. It’s not a direct path to change. Recognizing that we are the system, part of this process also relies on changing our own ways of thinking and working in relation to youth outsiderness. We need to help each other stay in the space of exploring and letting our direction for collective action co-evolve with our shared learning.