Abstract: According to one embodiment, a system includes one or more processors operable to receive data indicative of an account associated with one or more investments by an investor in a target date fund. The processors are further operable to calculate a plurality of premium amounts for a plurality of negative guarantees, communicate an indication of the premium amounts and the negative guarantees, and receive an indication of a selection of one of the negative guarantees. The selected negative guarantee provides a guarantee that, at a realization date, an account value of the account will be at least equal to an amount less than a principal amount regardless of market performance of the target date fund. The processors are further operable to, at the realization date, determine whether the selected negative guarantee was met by the account value, and communicate an indication of whether the selected negative guarantee was met.