A portable media playing device incorporating a database-driven menu structure that comprises a display mechanism, navigation database, including a navigation record with a navigation description, an action database, including an action record with an action description, wherein the action database is customizable in accordance with a field of the navigation record. A display driver displays the navigation description. When the navigation description is selected, the display driver displays the action description. When the action description is selected, a digital synchronization system generates an extra action request (EAR) record that includes an action identifier and action data for storage in an EAR database. When the device is synchronized with a computer, a synchronization manager accesses the EAR database and updates the action database with any new action records.