Retirement outcomes often result from activities prior to retirement, thus we begin by considering the retirement decision. New survey data document several factors correlated with feeling forced to retire. Next, we use the Health and Retirement Study to consider US households’ wealth ahead of and through retirement, controlling for age, education, financial literacy, marital history, labor force experiences, health, social insurance participation, estimated longevity, bequest preferences, planning horizons, and sense of well-being. This chapter contributes insights into how households’ goals and resources lead to healthy aging and successful retirement. Controlling for circumstances, we identify preferences that relate to better outcomes.