Understanding how we judge effortfulness promises insight into the myriad choices we make each day. Here, we present research investigating a curious finding: In Dunn et al., 2019, individuals anticipated reading a single rotated word as more effortful than reading two upright words. This contravenes the expectation that the latter will take significantly longer. In Dunn et al. (2019) participants had limited experience engaging in the task beyond judging anticipated effort. In the present investigation participants performed demand selection and forced-choice tasks for which they read either one rotated or two upright words. We analyze results in terms of choice, accuracy, vocal onset time, and task duration. Participants still generally considered reading two words as less effortful (and preferable) to one rotated word but, interestingly, this tendency diminished as the task wore on. We discuss implications for understanding individuals’ effort-based choices.