A method includes generating a first interactive graphical user interface (GUI) that identifies one or more guaranteed income options to fund essential retirement expenses and receiving a selection of a guaranteed income option. The method includes generating a second interactive GUI that identifies one or more investment options to fund lifestyle retirement expenses and receiving a selection of an investment option. The method includes generating a third interactive GUI that identifies one or more unexpected liability coverage options and receiving a selection of an unexpected liability coverage option. The method includes generating a fourth interactive GUI that identifies one or more legacy planning options and receiving a selection of a legacy planning option. The method includes generating a retirement plan that identifies the selected guaranteed income option, the selected investment option, the selected unexpected liability coverage option, and the selected legacy planning option.