The role of the Chief Information Officer (CIO) in higher education is continuously changing, and the career path to becoming a CIO is not always well defined. As campuses consider succession planning, and as CIOs and those who hope to become CIOs think about filling the IT leadership "pipeline," the transformation both of information technology and of the CIO role can obscure the road ahead. Several valuable studies--such as the "EDUCAUSE Center for Applied Research (ECAR) Bulletin" "The Future CIO: Critical Skills and Competencies" and the Center for Higher Education CIO Studies--offer help to current and future CIOs in navigating this changing landscape. But the information in these studies is delivered as the aggregated voice of the crowd. As the studies indicate, there are actually many different roads leading to the destination, and each road has its own scenery, detours, and on-ramps. In this panel discussion, six current CIOs and technology leaders explore their individual journeys. They outline their backgrounds and their personal strengths. They talk about the backgrounds, strengths, and skills that will be needed for future CIOs. They consider the challenges of preparing the next generation of CIOs. They list the most critical competencies for current and future CIOs, and they debate whether these competencies are changing. The move from the current generation of CIOs to the next generation of CIOs will consist of many journeys. Continuing the conversation about these diverse paths, and about the evolving role not only of CIOs but of technology itself in campus-wide leadership, can help all IT leaders prepare themselves and their institutions for the transition to come. (Contains 3 notes.)