The aim of the study was to trace the consequences of insufficient sleep, in terms of chronic sleep reduction rather than acute sleep deprivation, on fatigue, mood, cognitive performance self-estimations, and daytime sleepiness in different age-social groups. The age group of the subjects reflects their social situation and their working time organization: adolescents (n = 191) obeyed the strict school schedules with starting times often before 08:00 h; university students (n = 115) had more flexible timetables; young employees (n = 126) were engaged in regular morning schedules or irregular daytime hours or day and night shifts. A questionnaire study determined the declared need of sleep, self-reported sleep length, chronic fatigue (using a scale comprised of eight fatigue symptoms and four mood and three cognitive items), and daytime sleepiness (Epworth Sleepiness Scale). The declared need for sleep decreased in subsequent age groups from 9 h 23 min in school children to 8 h 22 min in university students and to 7 h 37 min in young employees. Consequently, the discrepancy between preferred and real sleep length (sleep deficit) was the largest in adolescents: 106 min. Females showed a greater need of sleep than males (p = .025) and significantly more fatigue, mood, and cognitive problems; they also exhibited higher level of daytime sleepiness (p < .000). The sleep index (reported sleep length related to requirements) correlated significantly with all health issues in women (p < .000), while only with fatigue symptoms in men (p = .013). Actual sleep length was unrelated to mood and fatigue issues; the declared individual need of sleep and sleep index showed significant associations, especially in the group of adolescents. The most frequent complaints of adolescents included tiredness on awakening (46%), nervousness, and general weakness; university students reported excessive drowsiness (50%), tension, and nervousness; employees suffered mostly from negative moods, such as tension (49%), nervousness, and irritability. The findings of the study indicate that chronic sleep loss seems to affect females more severely than males. The associations of fatigue and mood with sleep need and sleep index were more pronounced in younger subjects. Surprisingly, fatigue symptoms in school children and university students were as frequent as in hard-working adults. Because the problem of insufficient sleep is already present in youngsters, their work time organization needs more attention.