Chicago: The who, the why, and the where (part 3 of "I'm in love with Chicago AND Northern Michigan)

Chicago: The who, the why, and the where (part 3 of "I'm in love with Chicago AND Northern Michigan)

I moved to Chicago on August 1st, 2012. I was three months out of college and had no idea what I was going to do for a living or how I was going to make it all work. My overall strategy: Eh, it’ll all work itself out.

What I knew: I wanted to be with Ashley and I wanted to be here in Chicago.

Why Chicago? 1. She was from the suburbs. 2. We had spent a semester together in New York City and loved the pace of a big city. To me, Chicago wasn’t the “next best thing” to New York. It was better. With Chicago, you get the big city without losing the Midwest. You didn’t lose being driving distance away from your parents. You didn’t lose by becoming a New York Knicks fan.

And by Chicago, I really mean Barrington, Illinois. I moved into my wife’s parents house. She was there too, which only makes it slightly less embarrassing. I had a temp job at a law firm over in Bannockburn. I’d drive over to the law firm in the morning, be greeted with giant stacks of green folders and legal documents. I’d go to a room, pull staples, scan all of these pages for $12 an hour. I used every spare second I had to find a different job. Find anything else, preferably in the city.

I landed a job two months later at The Chicago Tribune. Moved down to an apartment in Buena Park. When you’re proposing to someone’s daughter, it helps when you don’t live right down the hall.

The Good Ol Bad Times

We’re weird in the Midwest. We reminisce fondly about the hard times. The lean years. The struggles. But notice these don’t become nostalgic until years later. During the lean years it just kind of sucks. You’re broke. You’re pulling staples out of legal documents. You’re not thinking, “Yeah, I’m really glad I took that leap of faith.”

But seven years later, when my memory has had enough time to sugarcoat the law firm, I’m left with this overall feeling of, “I wouldn’t do it any differently.”

When I made the jump from Michigan to Chicago, all I knew was my who, my why, and my where. I had no idea about my what (what am I gonna do for a living?) or my how (how am I going to make this all work?). What I found: The What and the How are overrated. If you don’t have those figured out, it’s not a big deal. Worst case, you eat some PB&Js for a few months and get used to a credit card balance that never gets back to zero.

Seven years in Chicago is long enough to have your spots around the city. Places where you’re a local. Where it feels like a small town. I mentioned those fish restaurants up and down Diversey in Part 2. I feel out of place in there. But Galway Bay, the basement bar at 500 West Diversey, man, I view that place as my actual basement. I walk down the stairs, greet Chris at the bar. He pours the Guinness the same way they do in Ireland. Takes a couple of minutes to do it the right way and it’s why Galway Bay (along with Fado downtown and Irish Oak up in Wrigley) serve the best Guinness pours in the city. I don’t even have to place an order at Galway Bay. The one time I did, Chris replied in his Irish accent, “You don’t think I know your order by now?”

Seven years and you build a whole roster of your favorite spots. I go to Crisp for massive chicken wings, but I’ve heard Bird’s Nest might be even better. Lou Malnati’s for deep-dish pizza. I wish I’d discovered Gepperth’s sooner, the little butcher shop on Halsted with everything from steaks to elk to ostrich. The owner’s wife makes homemade meatloaf, baked beans, sauerkraut. Chicago may not have Gates or Arthur Bryant’s BBQ, but we hold our own with Fat Willy’s and Twin Anchors for ribs and Green Street Meats for beef brisket. Haymarket for Reuben Tuesdays and their weekend Bloody Mary bar. If I’m not in a rush, it’s hard to beat a trip down to Manny’s for an epic pastrami + corned beef sandwich or the best pastrami in Chicago at Fumare Meats down in the French Market. Those lunches are guaranteed to end with an afternoon nap. For dessert, there’s Sweet Mandy B’s for cookies and pies; Bobtail–now Johnson’s–for ice cream that isn’t quite Moomers or Milk & Honey up in Traverse City, but it’s a two-minute walk from our condo and they serve Crash a “Pup’s Cup.”

Home is the place where they serve your dog a bowl of ice cream.


Chicago may not have the Northern Michigan wineries, but we’ve got the massive Chicago Winery downtown. My friend, Jeff, works on staff there. Back in high school, I found out Midland High used to have a mascot named Vic the Lion way back in the 1950s. Senior year, we decided to bring the mascot out of retirement. We held tryouts. Jeff was the first one to audition. He walked out of the bathroom in the lion costume and that was it. I looked at Nolan, Nate, Grillo, Mrs. Albright. Alright. Well, that was easy. No need to see anyone else. Jeff was Vic the Lion. It truly was his spirit animal.

And then BottlesUp! on Broadway, across the street from The Laugh Factory. Melissa and her husband capture the spirit of those wineries on Old Mission Peninsula. It’s the type of place where you can walk in with no wine knowledge whatsoever, just ask a vague question, “Hey, so uh, we’re grilling some steaks tonight, I was looking for like a good red wine? Any recommendations?” You’re not met with any snobbery. There’s no shame in being a novice. “Here, take a look at this one.” And they dive right into a story about the wine. If you want to learn more, they offer wine pairing classes. Free tastings. Everyone’s welcome; including dogs. They have a bowl of treats right by the door.

What I love about Chicago, and this gets back to the whole Midwestern thing, is this spirit of warmth and encouragement to try new things. Take Second City or the iO. Improv comedy is Chicago’s great original art form. You walk into these places and there are photos of the alumni – Chris Farley, Tina Fey, Amy Poehler, Steve Carell, Stephen Colbert, Key & Peele. You leave these shows, like Improvised Shakespeare, and it’s like you just sat courtside for a Bulls game. And it should be intimidating. A feeling of, “I could never do that.” But that’s not the message of Second City or iO. They offer classes every night of the week. They want to share their craft, show you how it’s done.

You don’t have to become great at improv comedy. Don’t even have to be really that good at it either. It took me a few classes before realizing, “Oh wait, this is just a fun thing to do.” I didn’t become an improv performer, I’m way too slow, too in my head about the next move, but this “Yes And” idea totally changed how I view writing and, to some degree, life in general. Any time someone has an idea, for a business or a book, I immediately go with the “Yes And” support. I don’t care about a detailed plan. Or a business model. If you’ve got a who, a why, and a where, that’s more than enough. The rest will work itself out.

Seven years is enough to make a dent, but there’s still so much left to see in Chicago. I’m 1,500 words into this post and I haven’t even mentioned the museums, the steakhouses, the breweries. What it’s like to walk into Wrigley Field or Soldier Field for the first time. A Saturday at Green City Farmer’s market. Or great bookstores like Unabridged, Seminary Co-Op, Book Cellar, Myopic Books. I still need to go to Read Write Library. They accept anyone in Chicago’s self-published book, magazine, journals. Their mission is to tell the whole story of Chicago, so they have no barriers on who can submit their work. I also need to get over to Kibbitznest Books, Brews, & Blarney.

I still haven’t seen the city’s skyline from a sailboat or done the architecture tour on the Chicago River. Haven’t rented a kayak yet. Haven’t been to the top restaurants like Maple & Ash, Girl & the Goat, or Wherewithall. It’s crazy, Chicago has five of the top 10 most expensive restaurants in America. One of them, Alinea, was ranked as the #1 restaurant in the world, was featured in Chef’s Table on Netflix. Alinea is not far from Gepperth’s. There’s no signage. I used to ride a Divvy bike right past it. Alinea is a place you put in the “Someday” category. Maybe on the 10-year anniversary of pulling staples at a law firm.

Seven years and we haven’t even scratched the surface yet. You never really grow out of this city, you simply grow into it, finding new facets, new reasons to say, “I’m in love with Chicago.”

Previous Posts in the Series

Next week will be the finale, putting Northern Michigan vs. Chicago against each other in one last round. This series is building up to a new writing project called “The Midwest as a Foreign Country.” The overall thesis being: We aren’t flyover states. There are so many great things to see, do, eat, drink in the Midwest and for way too long we’ve been giving the coasts and foreign countries way too much credit. We have great things right here! Stay tuned for this new series on Long Overdue Books (site currently under construction). Also keep an eye out for “Here or There,” my new the book, which is still trending toward an October 15th release date. Thank you for stopping by the blog and see you next week!

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