Mitigating Paradox at the eSociety Tipping Point In the first two decades of the past Century, having as driving factor the automobile and its mass production, the command economy has radically changed our lifestyles, enabling the creation of offices, suburbs, fast food restaurants and unified school d- tricts. With the Internet as driving factor, socio-technical and industrial eNetworked ecosystems are about to change our lives again in these two decades of the twenty-first century, and we are just approaching the tipping point. As we have just reached the point where the tremendous changes fueled by concerted efforts in information communication technologies (ICT) research are unraveling the old society this is creating a lot of d- comfort, confusion and sometimes opposition from the traditional mainstream. This disconnect is being deepened even more by the rocketing speed of technological ICT advances. As technology is getting ahead of society, the old ways, although still do- nant, become more and more dysfunctional and we are experiencing an age of pa- dox as the new ways disrupt the way we used to do things and even the way we used to think about the world. Just like the major inventions that shaped the last century were made by 1920, it is expected that the major inventions that will shape the twen- first century are going to be made by 2020.