Two Decades after the birth of the World Wide Web, more than two billion people around the world are Internet users. The digital landscape is littered with hints that the affordances of digital communications are being leveraged to transform life in profound and important ways. The reach and influence of digitally mediated activity grow by the day and touch upon all aspects of life, from health, education, and commerce to religion and governance. This trend demands that we seek answers to the biggest questions about how digitally mediated communication changes society and the role of different policies in helping or hindering the beneficial aspects of these changes. Yet despite the profusion of data the digital age has brought upon us—we now have access to a flood of information about the movements, relationships, purchasing decisions, interests, and intimate thoughts of people around the world—the distance between the great questions of the digital age and our understanding of the impact of digital communications on society remains large. A number of ongoing policy questions have emerged that beg for better empirical data and analyses upon which to base wider and more insightful perspectives on the mechanics of social, economic, and political life online. This paper seeks to describe the conceptual and practical impediments to measuring and understanding digital activity and highlights a sample of the many efforts to fill the gap between our incomplete understanding of digital life and the formidable policy questions related to developing a vibrant and healthy Internet that serves the public interest and contributes to human wellbeing. Our primary focus is on efforts to measure Internet activity, as we believe obtaining robust, accurate data is a necessary and valuable first step that will lead us closer to answering the vitally important questions of the digital realm. Even this step is challenging: the Internet is difficult to measure and monitor, and there is no simple aggregate measure of Internet activity—no GDP, no HDI. In the following section we present a framework for assessing efforts to document digital activity. The next three sections offer a summary and description of many of the ongoing projects that document digital activity, with two final sections devoted to discussion and conclusions.