The purpose of this paper is to provide an understanding of the two concepts of liberty in continuity with the philosophical arguments conceived early in Berlin's thought, and to further clarify the value of “negative liberty” and its implications for educational research. Berlin, along with his colleagues at Oxford University, was primarily critical of the logical positivists. He took issue with the fact that logical positivists base their arguments on the “correspondence model,” which attempts to make a one-to-one correspondence between certain propositions and the world and pointed out three fallacies underlying such thinking. Through these points, we were able to clarify that the grasp of the world based on the“ correspondence model” has a problem in principle and to confirm that it was the prototype for the criticism of monism, which later became the core of his thought. Then, in the Two Concepts of Liberty, he develops the criticism that positive liberty grasps the world in a monistic way. Asserting the importance of negative liberty on a pluralistic foundation, Berlin finds the value of negative liberty in understanding it as a condition for the exercise of freedom. However, it became clear that such conditions and freedom need to be distinguished, and that while recognizing the importance of developing conditions, we must not forget the value of negative liberty itself, which is“ the absence of obstacles to possible choices and activities. Among several suggestions, I argued that we should be cautious about translating problems into a more understandable form, no matter how difficult they may be to solve.