Trends in health, well-being, stress and the psychosocial work environment were studied using repeated measurements over time. The role of health-relevant personality in predicting development over time and typical ratings was also assessed. 517 individuals were included. Health-relevant personality 5 inventory (HP5i) was used to assess personality: HW-11 was used for repeated assessment of outcome measures. There were clear seasonal variations over time. Multilevel growth curves demonstrated that some changes over time could partly be explained by higher levels of negative affectivity at baseline. Individuals’ typical ratings were predicted by health-relevant personality. Those with higher negative affectivity typically perceived worse health, well-being and psychosocial work environment. Health-relevant personality seems to be associated with changes in health, well-being, stress and the psychosocial work environment over time. The findings highlight the importance of regular assessments of these indicators as they clearly vary over time and the trends seem to follow seasonal patterns.