This article aims to document the impact and timing of the transition to retirement on two dimensions, cognitive and affective, of subjective well-being (SWB) in the Swiss context. The effects on individuals’ emotions—i.e., positive and negative affects— and life satisfaction are studied while taking into account working conditions prior to retirement, the timing of entry into retirement and social participation. Based on the Swiss Household Panel (SHP), dataset on a representative sample of individuals living in Switzerland analysed from the life course perspective, our analyses are performed separately for women and men, and controlling for demographics (age), and economics parameters (household income, education level, satisfaction with financial situation, etc.). We adopt a life course perspective and use a multilevel approach (mixed linear model) to study individual trajectories on both the short- and the mid-term. The results show that working conditions play a key role in shaping individuals’ affective and cognitive well-being after retirement, and this especially for men. Positive work identification is detrimental for SWB after retirement; conversely precarious working conditions before retirement increase positive feelings after this transition. Women seem to enjoy a smoother transition to retirement, perhaps because it affects fewer dimensions of their lives. However, they seem to suffer more than men from the reorganization of interpersonal ties that retirement brings. Nevertheless, women whose professional trajectories are similar to those of men suffer more during the transition to retirement. These results demonstrate the importance of work as central in structuring people’s lives. Thus, people who are less involved or identified with the professional sphere tend to enjoy a smoother transition. Finally, these results highlight the heterogeneity in the transition to retirement and the necessity of considering the wide variety of preretirement professional trajectories in the Swiss context.