What is the nature of real (substantive) freedom in our society? Here, I shall present a new theory of liberalism which I call “growth-oriented liberalism.” First, I examine Isaiah Berlin’s concept of positive and negative freedom and raise a fundamental problem regarding freedom: Freedom is a paradoxical ideal. I shall identify two paradoxes: one concerns ordinary freedom and sophisticated values, and the other bears on “liberation” and the apathy of individuals or of groups. How can we overcome these paradoxes? To respond to this question, I shall examine Charles Taylor’s argument on positive liberty (freedom) and extend its implications. The issue is all the deeper as a society is closely knitted as a community, which is a typical trait told about Japan. By going beyond Taylor’s communitarian way of thinking, I shall endeavor to build a new theory of freedom by proposing three principles: the principle of virtue (self-esteem), the principle of generative change, and the principle of differentiation. I argue that the touchstone of free society depends on how we design our social governance based on these principles.