The aim of this study was to explore the factors that affect an individual's happiness while transitioning into retirement. Recent studies have found that workers often view the idea of gradual retirement as a more attractive alternative than a “cold turkey” or abrupt retirement. However, there is very little evidence as to whether phasing or cold turkey makes for a happier retirement. Using longitudinal data from the Health and Retirement Study, the authors explored what shapes the change in happiness between the last wave of full employment and the first wave of full retirement. The results suggest that what matters is not the type of transition (gradual retirement or cold turkey) but whether people perceive the transition as chosen or forced.