In a world where interactive displays are becoming increasingly embedded into the architecture we inhabit, this short paper contributes a case study of how we might meaningfully engage such displays in daily life. We designed Doodle Daydream, an LED grid display with mobile interface which acts like a shared sketch pad. Users contribute their own custom drawings that immediately play back on the display, fostering moment-to- moment playful interactions. Doodle Daydream was deployed in an office for 10 days. Interactions with the display were often playful and imaginative, like pausing for a moment during the workday to take a break or daydream. Doodle Daydream is a work in progress, with future plans for installations in a lobby and near the campus entrance, frequented by visitors and tour groups to the university.