A system and method for assisting users in selecting and prioritizing financial or business goals, and determining a cash flow designed to meet those goals. The user provides, or authorizes the provision of, financial information, which is used by the system to calculate an initial cash flow. The system actively assists the user in selecting and planning for a variety of financial goals, automatically calculates and determines the financial requirements to achieve each of the goals, structures financial products or plans for each goal, and determines whether the user has sufficient assets and/or cash flow to fund or achieve the goals. Goals are prioritized according to a set of business rules, and cash flow elements and goals can be modified or changed according to a variety of business rules in order to fund or achieve the goals.