The two most ardent critics of collectivism in the 20th century were arguably Ludwig von Mises and Ayn Rand. Mises was a hard-nosed economist and political economist; Rand was a hard hitting novelist and philosopher. Mises attacked the economic and political workings of collectivism; Rand attacked the morality and aesthetics of collectivism. This essay discusses the relationship between these two modes of argumentation, what I will term the “head” and the “heart” arguments and why the “head” must be used to temper the “heart”. Both Mises and Rand emphasized the primacy of private property in their defense of individualism. Whereas Mises was using the “head” argument to emphasize the role of private property as the necessary institutional framework for rational economic calculation, Rand appealed to the “heart,” emphasizing the role of private property in securing the conditions necessary for the operation of human reason. I then discuss why a “heart” tempered by the “head” is still nevertheless a beating “heart”. The essay addresses the relevance of the relationship between technical economics and social philosophy and explains why the abysmal failure of collectivism should be seen not as a weakness of humanity, but as a failure of the ideal.