This symposium presents cutting-edge investigations that highlight some of the lesser studied complexities of the retirement security and planning conundrum. The first presentation will focus on the effect that self-employment in later life has on financial, physical, and mental well-being, in comparison to wage-and-salary work, raising some potential concerns about the precarious nature of self-employment for many older adults despite it often being touted as an exciting, money-making prospect in retirement. The next two presentations will explore ethno-racial and gender disparities that exist with regard to employment status and retirement planning among older workers—some of the least understood variables in the retirement decision-making literature. The first will focus on identifying the antecedents of discrepant retirement intentions and behaviors in the Hispanic population, in light of recent evidence suggesting that there might be unique strains on retirement planning processes within this group. The second will use a gendered life course lens to examine how workplace and family factors contribute to an individual's decision to retire earlier or later than what is normative within their workplace. The fourth and final presentation will address how growing student debt over the life course is potentially becoming a new type of economic shock to retirement savings and planning. Drawing on hot-off-the-press focus group data, this study explores how individuals with significant debt are thinking about these unique pressures and concerns in later life. A discussant will comment on how these various papers contribute to our understanding of aging, work, and retirement in this era of increasing longevity and will relate the discussion to the American Academy of Social Work & Social Welfare's Grand Challenge to Advance Long and Productive Lives.