Starting with Doug Engelbart's Mother of all Demos in 1968, we've been on a technological tear for the last 50 years. However, the world and context of Engelbart, and the needs and opportunities for technology, were drastically different from today's. So while we continue to build out and enhance the roadmap set in the days of the Cold War, conversational software opens up and presents new ways to weave technology into our lives in ways that are both diffuse and profound, and meet the user — us humans — where we are, rather than asking us to modify ourselves to fit technology.