A system and method are disclosed for analyzing an individual's financial information and generating advice related to financial payment and negotiation strategies specifically tailored to the individual's current economic situation. This process is accomplished through the use of a primary support graphical user interface (GUI) which contains, among other things, descriptive icons representing distinct financial scenario categories. A user obtains information regarding the individual's current economic situation and selects a descriptive icon which most closely corresponds to that situation. A graphical window is then displayed which contains a set of predetermined questions and corresponding predetermined answers. The user inputs answers to the questions based on the individual's input. The user then instructs the system to generate advice on payment options and negotiation strategies most relevant to the individual's situation. The advice is displayed and the user relates the advice to the individual.