Over time, the responsibility for providing for a financially secure retirement has shifted more towards the individual. A number of implicit assumptions about perspectives, behavior, and individual choices underlie this shift. These assumptions presume that individuals are well-informed and reason unemotionally; that they process information correctly; and that they take rational decisions and act to maximize their own welfare. Empirical evidence, however, shows that such maxims do not often guide individuals actual behavior. Building on a new structure applied to insights drawn from behavioral finance, this book analyzes the perspectives of individuals with regard to their financial situation in retirement and compares the actions they take with ideal behavior. The work provides new insights into the broadly defined topic of individual retirement-specific financial planning behavior. The research builds on over 500 interviews with affluent individuals in Germany and contributes to defining ways in which policy-makers, financial planners, and individuals themselves can improve financial provisioning for retirement.