Are we just not very bright, a little crazy, or too insecure to do something else? Or are we having fun, working with some of the brightest people on the planet, and building applications that may actually change things for the better? Most of us enjoy wrestling with difficult technical issues. I, however, tend to avoid some of the really tough non-technical questions that come when I least expect them. For example, "what are you going to do when you grow up" stops me in my tracks. In this session, we shall explore some hard questions like "why is it so hard to get things done in higher education, particularly improving learning with technology," "how can we learn to avoid mistakes others have already made," and "how can we help to make things improve faster?" In addition to my own ideas, I shall provide some potential answers to these questions from IT leaders who have preceded us and also from current Snowmass attendees.