Some people experience cumulative advantages or disadvantages at birth and during their lifespan that determine future life course outcomes. Health disparities and systemic inequity can define a negative trajectory for some minority and underserved communities. Without intervention, such inequity can spiral and eventually affect more and more areas of an older person's life, much like cumulative disadvantages. This research proposes that older adults can improve their situation through targeted support factors that systematically improve lifespan areas. Eventually, more adults can experience the cumulative advantage effect as life progresses. The dissertation consists of a systematic literature review to evaluate literature that isolates degree-level education as a predictor of successful retirement transition planning. This foundational information is used as a basis for identifying constructs in two follow-on studies of the longitudinal National Health and Aging Trends Study (NHATS) Wave 9 public dataset. We explore factors supporting readiness for retirement and retirement transition in later life using data of older adults aged 65+. Multiple regression, exploratory factor analysis, and partial least squares structural equation modeling (PLS-SEM) are used to gain a multi-angle view. The results showed that degree-level education influences higher salaries, improved healthcare access, and financial literacy. In addition, old age has an increased risk of physical pain and chronic diseases that affect activities of daily living and independence in retirement, regardless of financial resources. Declining health can lead to social isolation and depression for older adults.