I start this paper with the notion of liberalism in a philosophy realm and manifest different thoughts of scholars and liberal theorists. I continue with explaining the notion of positive liberalism and manifest the complexity of the notion of positive liberty and the shortcomings of the concept of positive liberty that one can identify. I end this paper with a conclusion why I believe it is not possible to articulate a clear and plausible account of positive liberty. Among scholars and theorist of liberalism, one can determine a variety of definitions of liberty. Some scholars prefer to use the term freedom instead of liberty but both terms can be used interchangeably. I agree with Cranston that a liberal, by definition, ‘is a man who believes in liberty’ (Cranston 1967, p. 456). It is this human rationality that makes liberty in the realm of philosophy a complex issue. In the case of individual freedom, it was Mills who provided an imperative theoretical framework in On Liberty. Mills developed a concept that identified the best environment for individual and social progress based on one simple principle (Mills 1991, p.30). Mills strongly believes in the incompleteness of knowledge and the shortcomings of humans and used this as the fundament for his argument of the value of individual choice. This individual choice, Mills argues, can only be constrained by the harm principle which Mills defines as ‘the only purpose for which power can be rightfully exercised over any member of a civilized community against his will, is to prevent harm to others.’ (Mills 1991, p.30) However, the individual freedom that Mills attempted to define has its practical implications.