This study analyzed a social problem-solving workation in Kamaishi, Japan, focusing on the “hitohada nugu” experience, a cross-boundary and other-oriented contribution and relationship-building experience. The results of interviews with stakeholders of the work experience, including company managers and participants, intermediaries in the host local community, and government officials, as well as a questionnaire survey of all participants, indicated that employees who participated in the program learned and grew through their inexperience in Kamaishi, which was different from their work experience. On the other hand, the local community and companies that plan and operate the program face a dilemma in explaining the effects of the workation on the company's business, the solution to local issues, and the learning and growth of employees.