This study explored retirement transitions and further examined whether phased retirement was financially and psychologically beneficial for older adults in the United States. With data drawn from the 2010 and 2014 waves of the Health and Retirement Study data set at two time points, four years apart, this study analyzed 4,345 adults aged 55 to 80 using chi-square tests, one-way analysis of variance tests, and ordinary least squares regression analyses. Results showed that 65% of respondents continued to work full-time, whereas 13% chose to engage in phased retirement, and 17% of respondents immediately retired from the workforce. Overall, those who participated in phased retirement reported higher mean total household wealth and fewer depressive symptoms than those who immediately retired. However, this study found no strong evidence that retirement transition was significantly associated with total household wealth and depressive symptoms in the sample after controlling for total household wealth, depressive symptoms, and other individual difference variables at baseline. These findings highlight the importance of understanding the implications of decision-making on retirement transitions among older Americans.