This chapter portrays two thinkers, John Kenneth Galbraith and Amartya Sen, who set out with a qualitative conception of freedom. Both took offense at the contemporary state of affairs in economic policy and, by extension, in economic theory and business education. On their view, neoclassical economics has become myopic by hewing to merely quantitative parameters. However, by extricating from the realm of economic analysis all qualitative and normative considerations, economics has impoverished itself and has robbed economic policy of the requisite means to progress towards a more ecologically, socially, and morally sustainable order of business. As a consequence, Galbraith and Sen reject the merely quantitative conceptions of economic and political liberty buttressing conventional economic wisdom. Instead, they fend for a more self-critical notion of liberty that intellectually and practically realizes the qualitative dimension of freedom in a democratic fashion. Thus, they renew an argument that had already had much currency in metaphysical theories of freedom, i.e. that freedom must not only be pursued in substance but also in procedure. People should not only be passive recipients of the rights and benefits of liberal orders, but also, importantly, their active and transformative architects.