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Traditional “endangered” approaches in linguistics tend to impose Western epistemologies of languages on marginalized Indigenous language communities such as the Ryukyus. Instead, by using a collaborative approach, we ask for a change of approach from research on the Ryukyus to research with/for the Ryukyus. This article is a reflective study of collaboration in particular cases. We aim to address the issues of relationality between communities and researchers—how can communities initiate work with like-minded linguists to suit their own needs? Thus, we respond to this question to open a conversation on why insider/outsider collaboration is essential. Using our experiences of carrying out our research in different parts of the Ryukyus reflectively, we aim to provide a practical guide for collaboration that is necessary for both the good of communities and the field of linguistics. Through continuous cooperation and collaboration, we can engage in active decolonization of the field of linguistics and language documentation. We suggest that decolonization cannot be achieved without collaborative and ethical research practices based on Indigenous epistemologies. We conclude the paper with ideas of research approaches based on Ryukyuan Indigenous epistemologies, which require a transformation from individual approaches to community-based-relational approaches.