In this study, we planned and implemented a training program to improve self-directed learning through manual writing for social studies curriculum and textbook developers in Cambodia. Further, we conducted individual interviews with trainees to analyze their self-directed learning from a postcolonial perspective. As a result of the training, the learners were able to realize a variety of self-directed learning in their individual contexts beyond other-determined learning. The authenticity of the performance task, a manual written in Khmer by a Cambodian for the future of Cambodia, liberated their learning and restored their autonomy. Further, the learners did not question the content of the training, and their perceptions were not limited to the subject-specific nature of social studies education. This is because of the hegemony of Japan as a donor country and the understanding of the Cambodian government of the learning needs of the learners’ political position. The international cooperation project in social studies pedagogy was aimed at building a peaceful, democratic, and sustainable society through the transformation of social studies education. However, a dilemma became apparent that the more we aimed to liberate learning with postcolonial awareness, the further we diverged from the goal of the project. This research suggests that, in order to overcome this dilemma, we need to engage as co-inquirer in training programs, such as curriculum formation and social studies goal setting, with an awareness of academic postcolonialism, while staying close to the learners’ concerns.