In today’s environment, consumers are increasingly responsible for their retirement accumulation and decumulation decisions. There are products in the market that can assist consumers with these decisions, and the effectiveness of these products is dependent upon individual preferences. Risk willingness is one of the fundamental aspects of retirement planning, and as such, is an important factor that can match consumers with appropriate products in the market to suit their preferences. Annuities are insurance products designed to help mitigate certain retirement risks, such as longevity and investment risks. If a risk averse consumer chooses to transfer such risks from themselves to an insuring company, they may find more satisfaction in their retirement income accumulation and decumulation decisions. It is important to properly identify, measure, and compare an individual consumer’s or household’s financial risk willingness across important demographic measures. Often, a problem when comparing across demographics is that comparative groups are imbalanced by representation, response, and/or measurement. Methods that do not control for this imbalance when comparing one group to another often will have biased estimates, spurious results, and inconclusive hypothesis testing. Propensity score matching allows for comparison across groups that are balanced based upon relevant and theoretically motivated variables. When used appropriately, a researcher can confidently compare across important demographic groups in order to better estimate any potential differences that may have an impact on retirement accumulation and decumulation decisions.