As insomnia develops, one may start to worry about not sleeping. One of author’s friends had a stressful management position over which she started to lose sleep. She then feared that the lack of sleep would negatively affect her work performance. This made it even more difficult for her to sleep because the thought of underperforming increased her anxiety. One can see how this can become a cycle of worry and sleeplessness. This chapter discusses some of the common worries that are linked to insomnia. By examining these topics in the light of day, rather than ruminating during a sleepless night, we achieve a more balanced view of our sleep problem and its effects. Stressful thoughts at night have a way of expanding to fill the dark spaces around us. The chapter provides information that will help to bring one’s sleep-related worries down to earth.