As wearable computing goes mainstream, we must improve the state of interface design to keep users productive with natural-feeling interactions. We present the Personal Cockpit, a solution for mobile multitasking on head-worn displays. We appropriate empty space around the user to situate virtual windows for use with direct input. Through a design-space exploration, we run a series of user studies to fine-tune our layout of the Personal Cockpit. In our final evaluation, we compare our design against two baseline interfaces for switching between everyday mobile applications. This comparison highlights the deficiencies of current view-fixed displays, as the Personal Cockpit provides a 40% improvement in application switching time. We demonstrate of several useful implementations and a discussion of important problems for future implementation of our design on current and near-future wearable devices.