“Facts are stubborn things, and whatever may be our wishes, our inclinations, or the dictates of our passions, they cannot alter the state of facts and evidence.” –John Adams This paper addresses the complexities of book digitization. In many ways, books defy easy categories that would allow the uncomplicated workflows many people assume are possible. I will examine how this unavoidable fact impacts planning and implementation of regularized book digitization, highlighting common problems and describing how they may be resolved or avoided altogether through careful planning. The paper includes a description of how my organization used a pilot project as an opportunity to build a coordinated workflow encompassing multiple activities across several departments within a large university library.