"Oh the Places You'll Go!" That Dr. Seuss book is a standard gift for graduates as they are sent out into the world-whether it's off to college or into the world of work. "You can steer yourself any direction you choose." What direction did school business officials take to get where they are today? The most recent ASBO International membership survey gives some insight into the journey from graduation to the school business office. According to the 2012 survey, 37% of the respondents came from a background in business before joining the school business profession. Only 12% followed the "traditional" route of moving up from the classroom into administration and school business. Increasing numbers of members also report coming out of other areas of government or were attending college immediately prior to entering school business. The path to school business is as diverse as the backgrounds of those who now dedicate themselves to ensuring students have the resources they need to be successful in school and beyond. The author asked three school business officials to share with her how they got to where they are today, what they learned, and where they see themselves five years from now. This article presents their stories about the places they have been, where they are, and where they are going.