Increasingly rapid and dramatic changes in technology and business make predicting one year close to impossible and to 2020 beyond impossible. However, it is critical to attempt to plan for 2020 to overcome the persistent failures of business and technology to address real problems, such as providing holistic, human centered solutions. Due to Cartesian basis for science, technology, and much of western thought, our disjoint technologies offer point solutions, a cell phone for communicating, a computer for computing, the Web for buying books, and a Television for entertainment. While these point solutions are most often sold as solving problems while enriching and simplifying our lives, the opposite is often true. The power of ubiquitous voice and e-mail communications is overwhelmed by the volume of communications, the ever-changing and complex devices on which to receive and send them, and the ever-changing services and service providers who offer them, even if 50% were not junk. This talk attempts to provoke thoughts on how to plan for 2020 to achieve holistic solutions in the convergence of computing, communications, entertainment, eCommerce, and more. We consider traditional factors such as constantly increasing automation and the speed of change and innovation, but will focus on factors that make prediction almost impossible, including how good technology should disappear, technology convergence producing unanticipated opportunities, disruptive technologies that displace technologies and disrupt existing products and businesses, and unpredictable paradigm shifts, such as the Internet, that change everything. The talk concludes with a vision of holistic, human-centered solutions that enhance the human experience enabled by converged, Next-Generation technologies.