As a general rule, individuals tend to be optimistic in predicting when they will complete an upcoming activity. Building upon the ease of generation theory, we examined how dividing the planning process into multiple steps would impact the magnitude of optimism in “real world” planning. In Experiment 1 we found a decrease in optimistic prediction bias when individuals described their plans by generating a relatively difficult five-step, rather than a relatively easy two-step, optimistic scenario. In Experiment 2 the bias diminished when individuals generated the easy, rather than difficult, pessimistic scenario. In Experiment 3 the bias decreased even among individuals who generated the easy, rather than difficult, optimistic scenario when they were led to negatively interpret the feeling of ease.