In this article, the author discusses how in principalship, prospective leaders are expected to conquer the motorway without any behind-the-wheel experience. University programs alone never will be enough to prepare principals for the day-to-day challenges of the job. The dilemma can be framed this way: In the university you spend extended periods of time reflecting about a problem and solution. In the principalship, problem resolution is expected yesterday. In a university class, you might read a case study on searching a school locker for drugs and debate with classmates whether the search should be conducted. As a principal, you hear about possible drugs in a locker 10 minutes before dismissal and you need to act quickly. Principals manage complex organizations with unpredictable demands. No matter how ready candidates think they are, it is always a shock to their system when they finally get buckled into the driver's seat.