Much has been written to inform academics about revising a dissertation and completing a book, but most of this advice focuses on first-time authors. By contrast, there is little advice directed toward more experienced academic authors that considers the conditions they confront when writing a second book, such as increased demands on them to provide institutional and professional service. Second-time authors may also enjoy the assurance that comes from having established a relationship with a publisher or having achieved tenure. This article offers three lessons about how writing a second book is different from writing the first. It considers how experienced authors’ relationships with publishers may change with a second book, and it examines ways to situate a second book in the course of a long academic career.