Successfully adjusting to retirement represents a major challenge for many older workers. Following the temporal unfolding of retirement process (i.e., preretirement, transition, and postretirement phases), the present study draws on the resource-based dynamic model of retirement adjustment to investigate how a diverse set of preretirement personal resources (i.e., physical health, mental health, financial well-being, family support, proactive personality, and general cognitive ability) impact postretirement change trajectory of life satisfaction through the pathway of retirement transition experience (i.e., retirees’ subjective experience in terms of how well they are adjusting during the transition phase of retirement immediately after the workforce exit). Using multiwave longitudinal data from 667 Chinese older workers transitioning into retirement collected with a prospective design over 2 years, we found positive effects of the levels of preretirement mental health, financial well-being, family support, proactive personality, and cognitive ability on retirement transition experience. We also found positive effects of the changes in physical health, financial well-being, and family support on retirement transition experience. Retirement transition experience, in turn, was associated with older workers’ postretirement change trajectory of life satisfaction. Our findings highlight the importance of the transition phase of retirement, as well as the role of retirement transition experience during this critical phase in explaining the relationships between preretirement resources, in terms of both their levels and changes, and postretirement changes in well-being.