We recently shipped new features to Intercom's support capabilities, including advanced ticketing workflows and richer reporting. To improve the usability, intuitiveness, and polish of our main product navigation, we analyzed complexity creep that had crept into it over time. We gained a deep understanding of the problem by talking to customers, who identified two discrete issues: unclear icons and unintuitive ordering of items within the navigation. By focusing on these problems, we made simple yet impactful improvements, including reordering our navigation to prioritize Inbox and redesigning our navigation icons based on four principles: obviousness over prettiness or cleverness, passing the squint test for individuality and collectivity, drawing from our logo's anatomy, and sweating the details. We also polished the executional details, such as hover states and product icon alignment, to create a more intuitive and polished navigation that combats entropy by continually revisiting fundamental parts of our product to rationalize, simplify, and repair.