Reports consistently indicate that baby boomers are unprepared for retirement, a potentially long phase of life. Many studies have targeted financial planning to the exclusion of other important aspects of retirement planning, namely, the concomitant psychosocial factors. Accordingly, this study examined retirement planning in the following five key areas: general, financial, work, health, and lifestyle. Specifically, this study's primary purpose was to examine the relationship between both role clarity and internal locus of control and past, current, and future retirement planning. Secondary purposes were to examine: a) the relationship between internal locus of control and role clarity; b) the relationship between internal locus of control and past retirement planning; c) the effect of past retirement planning on current and future retirement planning; and d) the effect of past retirement planning on role clarity. The study also examined the influence of personal background factors on past, current, and future retirement planning and on internal locus of control. Multivariate analyses highlight the role of past retirement planning and indicate the importance of funding, implementing, and maintaining retirement education programs to engage baby boomers in retirement planning. The findings can be used by researchers, policy makers, practitioners, and retirement planners.