Teaching is a complex collection of creative actions with ongoing consequential choices and decisions; therefore, it necessitates educators' ongoing reflection. As educators who currently serve art teacher candidates at Kutztown University of Pennsylvania, a small public university in the rural Northeast, the authors constantly seek to rework themselves and expand their lens on the world, and they continuously think about how they might inculcate reflection as a habit of mind in their teacher candidates who are embarking on a lifetime of collaborative learning. Within the pandemic's uncertainty and daily onslaught of the unforeseen, they noticed teacher candidates finding it challenging to step back and reflect. This climate was an opening for reflection as a means for sensemaking. The teacher candidates' reflections easily moved away from asset-based introspection to negative feelings such as regret and judgment. This facilitated the need to house and support their acts of reflection in a community of practice, a safe home to debrief and unpack in, with, and through a cohort of others.