Psychosocial stress is widespread worldwide and particularly affects young adults. There is a close and bidirectional relationship between sleep quality and mental health. Sleep duration, which is an important feature of sleep quality, shows both intra-individual variations and inter-individual differences. Internal clocks control individual sleep timing, which, in turn, defines the chronotype. On workdays, however, the end and duration of sleep are largely limited by external factors, such as alarm clocks, especially in later chronotypes. The aim of this study is to investigate whether there is a relationship between sleep timing and duration on workdays and measures for psychosocial stress, such as anxiety and depression; subjective workload; and the subjective impact of a high workload on sleep. We used a combination of Fitbit wearable actigraphy data and a questionnaire survey of young, healthy medical students and calculated correlations between the respective variables. We found that a shorter sleep duration on workdays is associated with a higher subjective workload and a higher subjective impact of a high workload on sleep, which, in turn, are associated with higher measures of anxiety and depression. Our study contributes to understanding the importance of sleep timing/duration and their regularity on weekdays for subjectively perceived psychosocial stress.