When I was growing up in Michigan, I couldn’t wait to get out. There was no view as thrilling as the map of a big city laid out from an airplane window at nightfall. Each time my parents took us on a trip, I plotted my escape. I poured over our weekly issue of The New Yorker, memorizing the places advertised in the back of the magazine.

My years living in big cities had given me an unexpected education in getting the most out of small city life.

On Sunday afternoons, my brother and I sat in my godmother’s car, playing the game we called “Driving to Chicago.” (Thankfully, her keys were safely put away.)

Eventually, I got my wish. I've lived in Chicago, New York, Washington, and Tokyo. And now, I’m back in Ann Arbor, the town where I was born. Only I’m not standing on our Main Street and despairing...