In the mid-1960s Ithiel Pool was invited to participate in an exercise to forecast the future of the international political system during the next fifty years. In the next decade his MIT colleague, Nazli Choucri, co-edited a book about forecasting in international relations, followed-up the initial article, and invited Ithiel to contribute the second selection, with reflections about how his predictions were turning-out and the enterprise of social science forecasting. Pool was writing his book, Technologies of Freedom, that was designed to influence the future by making a forecast that he wanted to become self-defeating. Pool’s book argued that the legal doctrines that justified earlier regulation of telecommunications technology could produce an extraordinary restriction of freedom if they were—as he predicted could happen—extended thoughtlessly to cover new, digital forms of electronic communication. His book defined thinking about these issues and he proposed new policy guidelines that would, if adopted, make the forecast wrong.