Timothy Sandefeur: The Terrain Is Easier to Judge in the Neighborhood of Liberty Than in the Neighborhood of Unfreedom

As a matter of procedure, starting with a presumption in favor of freedom is preferable because each step people take away from a state of liberty can be justified in theory by measuring whether they are better off. When two people sign a contract, they bind themselves, and in that sense are less free. But they consider themselves better off, and that is good enough, as long as they harm nobody else. It is not so easy to justify the reverse – a movement from a state of total unfreedom to one that is freer – because each step affects far more people. The totalitarian state is frozen solid, so that every action inflicts consequences on everyone else, and the slightest deviation from rigid order must therefore receive the approval of everyone affected. This means it is not always possible to determine whether people are better off at each step when they move in that direction. This, writes Epstein, ‘is why the restoration of even modest elements of a market system seem to pose such radical problems for Eastern European and Third World nations.’
— Timothy Sandefeur, The Permission Society: How the Ruling Class Turns Our Freedoms into Privileges and What We Can Do About It