Nobody likes to think about that inevitable time when staying in one’s current job no longer makes sense. Perhaps the time to leave comes as an unpleasant surprise. Or maybe accumulating problems are readily apparent. But in many more cases, the viability of the chief information officer (CIO) job slips and degrades without obvious signs. Knowing when to move on is a painful topic, but it is also a key professional skill and potential career saver. Neither individuals nor institutions recover easily when the exit becomes a problem.