This paper from the Digital Equilibrium Project is meant to foster a new, collaborative discussion on the most pressing questions that could determine the future safety and social value of the internet and the digital technologies that depend on it. It urges governments, corporations and privacy advocates to put aside the polarizing arguments that have cast security and privacy as opposing forces, posing four fundamental questions that must be addressed to ensure the digital world can evolve in ways that ensure individual privacy while enabling the productivity and commercial gains that can improve quality of life around the globe.