The invention encourages users to not only pay themselves first, but to pay themselves first in the largest amounts possible, even if they are not able to fully pay outstanding debts. In general, the invention obtains information related to the user's income, income sources, user's debts (e.g., bills) and user's goals, then provides recommendations related to the prioritization of paying certain bills and the amount to pay for each bill based upon, for example, savings goals, minimum amounts due, due dates and available income. The invention also determines a payment hierarchy which includes transferring funds to the user's savings account prior to paying all or a portion of certain bills.