Chicago might have too many nicknames. We’re the Windy City. The City of the Big Shoulders. City in a Garden. The Second City. The Third Coast. New ones seem to crop up all the time, and I’m saying right here that you’ll never get me to call it “Chi-Town.” But I’ve always been partial to “The City that Works.” I have more than a decade working for the city in urban planning, parks and transportation, and for me, “The City that Works” means we’re a city that, well, works. And we work hard and smart. We grind, adapt, move forward, build and rebuild, figure it out, get big things done, and we ought to work well for the people who live here. The tilt toward action, movement, is part of the appeal. The current “Horizon Lines: Visions for Chicago 2050” design competition launched by World Business Chicago asks us to propose bold and transformative ideas for Chicago’s future. This includes how we move around cities and what we might do with the streets and sidewalks we share that make up the public realm. In short, what transportation future should the City that Works work toward? It’s a critical question because the future is upon us. Autonomous vehicles. Delivery drones. Sidewalk robots. Electric air taxis. Traffic management powered by artificial intelligence. Vehicles and infrastructure that talk to each other. An unending number of new technologies and tools seem to land on our streets every day. To prevent the proverbial tail (technology) from wagging the dog (our city), we need to design for the public realm we want, and the right tools will follow. Too often, our conversations about mobility confuse the tool with the job we want the tool to perform. The job is to move us from where we are