Today’s informatics geography contains many perils for those who take the journey from system design to routine use. That journey has many parallels with the experiences of a travelling Hobbit in Tolkein’s Lord of the Rings [14]. Many of us spend all our days in the Shire, which is a wonderful place. Here we conceive new information frameworks, architectures, terminologies, and ontologies, intended we are sure for widespread use throughout the land. We never however leave to find out if they are. Everything however, changes when you leave the Shire and cross the River of Implementation, and bring a real information system into actual use. The people you meet bring you unanticipated problems. When you cross the Workaround Mountains you meet folk that are frustratingly expert at doing what they want to do, no matter what your technology tells them to do. The people in the Human-factors Marshes are expert at doing exactly what your technology tells them to do, even when it is the wrong thing to do. If you are really unlucky your journey will take you to the very dark place of Mordor, the home of large-scale IT failures. When you are here, you are always under the watchful, unforgiving, gaze of the Great Eye of Public Opinion. (Figure loosely adapted from [14]).