This paper took a challenge with regard to this radical reaction for the conventional orientation about modern education. Present challenges in education and its reform trials are all surrounded by the freedom issue. To the extent how the freedom has been achieved over the times and places, education has been shaped to its institutional form in that time and places. Answering the question, this paper reviewed the traditions of freedom in education in the beginning and further to the present phenomena of transnationalism in education. Concluding implication of the paper is that all individuals shall be free to choose education to create themselves, choose the language to communicate with others, and choose the space to live on the flattening world by globalization; on the space, they shall meet the people to live with and build the community to live in. Education, therefore, must keep its first priority of cultivating individual’s capacity to possess and enjoy freedom. Education must be freed from the school boundaries, particularly those of which are doing the police of the nation state.