Background: Our work/study culture is biased towards the circadian clocks of “morning types”, whereas “evening types” are forced to advance their weekday waking times relative to weekend waking times. Since the experimental research consistently reveals a >2 h difference between these two chronotypes in the positions of their endogenous circadian phases, we hypothesized the necessity to permit a >2 h difference between them in weekday waking times to equalize their irrecoverable loss in sleep on weekdays. Methods: A total of 659 and 1106 participants of online surveys identified themselves as morning and evening types, respectively. The hypothesis was tested by applying a model of sleep–wake regulation for simulating sleep times reported by 245 lecturers of these two types, and by comparison of sleep times of these types among these lecturers and 1520 students. Results: The hypothesis was supported by results showing that, if, on weekdays, an “average” morning type wakes at 6 a.m., the equalization of the weekday sleep loss of the two chronotypes would require the waking time of an “average” evening type to be no earlier than 8 a.m. Conclusions: These results may be implemented in a model-based methodology for the correction of weekday waking times to equalize weekday sleep loss.