A person has expenses to be paid according to a financial plan which identifies liquidating procedures for liquidating investments to generate funds for the person, where the funds are for paying the expenses. To implement the financial plan for the person, the financial plan is received at a plan defining module which produces based thereon a formatted list of sequentially applied liquidation rules. A plan implementation module is actuated upon a triggering event, after which the formatted list of rules is received at the actuated plan implementation module. The actuated plan implementation module applies the received list of rules to liquidate investments of the person and thereby generate the funds for the person.