Contemporary, “always-on,” US workforces have expressed frustrations with an increasingly disproportionate work-life balance. Building off of the concept of imaginative play, this project aims to address various “work tasks” in a more playful manner. Equipping the modern worker with a digital toybox can encourage even the most tedious “work tasks” to become exercises in creative problem solving and innovation. By exploring the intersection of work and play, new methods of productively incorporating playfulness into workflow may provide an alternative solution for facilitating a healthy work-life balance.