Japan Overseas Cooperation Volunteers (JOCV) are dispatched to a range of countries around the world, where they work with people from local communities to provide expertise and training in programs related to education, healthcare, and other kinds of technical assistance. Destination countries are often characterized as traditional societies seeking to preserve their own values and customs. In undertaking such work the volunteers need to understand how local values and customs may be practiced by the local community members and engage in a discussion of the desired “outcomes” based on the socio-cultural characteristics of the region. This will help to promote an understanding of both JOCV activities and the actual local conditions. This study presents the regional realities that manifested as a result of interplay between cooperative activities and the specific socio-cultural context of the dispatch region. Moreover, it suggests the need to evaluate the outcomes of cooperative activities from a socio-cultural perspective. This study focuses on the Pacific Islands region, where I have been conducting anthropological research since 1987. The regional characteristics of the Pacific Islands include a subsistence economy, in which non-industrial elements are prominent, and abundant and cherished interpersonal relationships (i.e., possessing the feature of mutual support). However, the locals can also be labeled as island people or people who seemingly lack ambition, do not want to work, and have no desire to improve; or, people who are merely waiting for aid. The majority of volunteers were disappointed with this unanticipated reality, though they came to understand it (and some to admire it) after a while. The volunteers attempted to resolve these conflicting feelings between their expectations and reality by idealizing an image of themselves as volunteers who “blend in” and mutually interact with the locals. Embracing this status served as a mediator, allowing the volunteers to internalize the regional characteristics and make the activities “their own.” Finally, this study demonstrates that, where attitudes diverge drastically from the Japanese work ethic and values, evaluations should focus on the unique interactions between volunteers and locals that occur in each society, workplace, and living space.