At this point, I want to make explicit two implications of the relationship between property and moral freedom developed above. First, a painful but necessary part of any freedom is the freedom to fail. Applied to our use of property, moral freedom requires the freedom to be poor, the freedom to be selfish, and the freedom to be undistinguished. If private property were obliterated so that no one could be poor or selfish or undistinguished, no one could properly be said to be free. And what's more, history and scarcity give us every reason to believe that some people not only can fail, but will fail.
Failure is the cost of freedom.
Second, the kinds of moral freedom I have addressed are linked to concrete, relatively small-scale properties. Massive, abstract, anonymous ownerships of stocks, options, and the like are legal fictions which, whatever their own virtues, weaken the bond between man and the material world, and hence weaken the moral freedom and responsibility which ownership engenders. In the classic Lockean understanding of property, individuals create possessions by mixing their labor with the material environment. The reality of global scarcity may give us reason to add to Locke's condition, but the purposeful labor of an individual is still a necessary starting point in understanding how it is that a person comes to be identified, in part, with his property. Indeed, the whole modern notion of a corporation divorces men from responsibility and reduces property to a disembodied and dangerous abstraction.