In 2002, Chicago magazine decided that it wanted to appeal to a younger demographic. At the time, I was part of that demographic, so I was invited, along with every other nervous greenhorn on staff, to lunch with the boss—an old-school journalist who wore a gray suit and ignored us in the elevator. On more than one occasion he had called me Jack, and I didn’t mind, so thrilled was I to be called anything at all.

Can’t say I remember much from that lunch, apart from an awkward conversation about “things your generation is interested in” and the fact that it took place at Maggiano’s. I recall that nobody at the table knew what to do with Chicago’s back page, real estate ripe for experimentation. Rather than seize the opportunity, I sat quietly with my eggplant Parmesan, terrified of splashing marinara on the boss’s Dartmouth tie. Another editor, perhaps to divert attention from herself, suggested that I be given a shot at the page, and I walked away from lunch with a challenge from the boss to pitch ideas.

To his surprise, I did. My ensuing memo included a survey of the smelliest spots in Chicago, a point-by-point comparison of Internet spam versus Spam the luncheon meat, an attempt to eat an entire 15-scoop sundae at Margie’s Candies in one sitting, and every other random idea that popped into my head. My superior must have thought more of me than I imagined—or less of my generation—because he went for it. “Let’s try it for a few months,” he said in a strange voice that I identified in the following days as desperation.

Eleven years and 131 columns later, I still can’t believe I got away with it. Somehow, each of the above ideas found its way into a magazine whose pages were once kissed with the prose of Terkel, Ebert, Erdrich, and Eig. Even as my column moved inland from the editorial Siberia of the back page and grew in size, my editors allowed me to cover whatever tickled me at the moment—as long as I met my deadlines and word count.

Hey, my neighbor jumped into a freezing Lake Michigan to save his dog. Sounds great. Do it. My wife’s colleague knows Obama’s neighbors. Go for it. Some guy re-creates medieval torture instruments in a barn in Indiana. Remember to expense your mileage.

When it was good, the page had a serendipitous vibe—the ideas often came by accident, and if you told me something interesting on the right day, it had a decent chance of landing in print (see lady arm wrestling, January 2013). Other times I planned for months, trying stunts I’d been dreaming about since childhood, such as re-creating the exploits in Ferris Bueller’s Day Off to see if they could be done in a day (September 2008; they can’t).

Through it all, I was encouraged to play with the format. I produced quizzes, open letters, mini-biographies, competitions, recipe cards, fake classified ads, the stuff that took forever to make and 30 seconds to consume—journalistic gummy bears. Common themes surfaced again and again: Who are Chicagoans? What aggravates us, amuses us, scares us, thrills us?

There’s no answer to that question—you can’t boil down eight million people to a series of traits—but that doesn’t mean I didn’t learn anything about this city. I learned that you can get banned for life from Whole Foods. I learned that the psychic on Ohio Street doesn’t know what she’s talking about. I learned that the man for whom Wells Street is named had his head cut off and his heart distributed to Potawatomi warriors and that Vija Celmins’s Night Sky #2 is a treasure at the Art Institute. And I learned that after we leave the ER, the doctors make fun of us all.

The subject was never really Chicago anyway; it was me. When I reported for jury duty, I enlisted a trial attorney to explain how to get out of it (September 2007), and when I heard that the inmates at Cook County Jail were being fed something called Nutraloaf, I drove to 26th and California to eat it (September 2010). As I struggled to make sense of this wonderful and vexing city and find my place in it, the column doubled as a therapist’s couch where I worked out issues and exposed mortifying secrets.

This freedom doesn’t happen often in traditional media, where first-person writing gets drilled out of students on day one of journalism school. Just report, tell the story, and get out of the way, professors instruct their charges. I have rarely heeded that guidance—nor could I. “You’ve got a real voice, Ruby, but your reporting is horseshit,” a professor once told me. The second half of that assessment would have crushed most any aspiring writer, but I was too thrilled by the first half to notice.

A columnist who harnesses the power of first-person writing develops a relationship with readers. If you’ve been reading me for 11 years, you know that I once believed that Lake Point Tower was sinking into the lake and that I conceived my third child during a 24-minute segment of The Backyardigans. This oversharing can be great, like the time I got my grandfather to talk about his experiences at the beaches at Normandy during World War II (October 2009). It can also be awful, like the humiliating colonic I got while seeking enlightenment through pain (December 2007). “Couldn’t you have made it up?” my father-in-law asked, a possibility that had never occurred to me.

“I have a shrine of your columns on my bedroom wall,” a reader once e-mailed, and I loved it, because in my imagination she looked like Scarlett Johansson. More than that, it was proof that words, whether tongue-in-cheek or with heart on sleeve, could engender such passion in a stranger. And if those words were mine, then maybe I knew where I fit into Chicago after all: on this page.

While Jeff Ruby continues as Chicago’s chief dining critic, this is his last Urbanist column.