From an aging research and life-course perspective, the transition to retirement marks a significant life-event and provides a unique opportunity to study psychological health and coping during a period of substantial change in everyday life. The aim of the present paper is to: (a) outline the rationale of the HEalth, Ageing and Retirement Transitions in Sweden (HEARTS) study, (b) describe the study sample, and (c) to present some initial results from the two first waves regarding the association between retirement status and psychological health. The HEARTS study is designed to annually study psychological health in the years before and following retirement, and to examine change and stability patterns related to the retirement event. Among a representative Swedish population-based sample of 14,990 individuals aged 60–66 years, 5,913 completed the baseline questionnaire in 2015. The majority of the participants (69%) completed a web-based survey, and the rest (31%) completed a paper version. The baseline HEARTS sample represents the general population well in terms of gender and age, but is more highly educated. Cross-sectional findings from the first wave showed that retired individuals demonstrated better psychological health compared to those who were still working. Longitudinal results from the first and second waves showed that individuals who retired between waves showed more positive changes in psychological health compared with those still working or previously retired.