Rule #1989: The Chicago Way
When Matthew went to college, I heard from him about every two weeks—usually with the routine call of everything is fine, classes are going well, and nothing to report. Basically, keeping me in the dark and failing to mention anything of substance. The standard nosey-parent report. No lies, but nothing incriminating either.
So when I got a call on a March morning in 2008 at 9:00 a.m. from Matthew’s older brother, Andrew, asking how Matthew was doing—and suggesting I should check on him—I was confused. The next conversation with Matthew went like this:
Dad: “What are you doing?”
Matt: “Eating breakfast.”
Dad: “What are you having for breakfast?”
Matt: “White Castle hamburgers.”
Dad: “Where did you get White Castle hamburgers in Shippensburg, PA?”
Matt: “The White Castle’s on Wacker Drive.”
Dad: “You mean in Chicago?”
Matt: “Yeah, that one.”
That’s how I learned my son was taking off from school mid-week and driving around campaigning for President Obama in Illinois, Indiana, Ohio, and New York. It wasn’t that he lied to me—in fact, he was very forthcoming when asked—I had just failed to ask the right question. And he wasn’t offering details without heavy inquiry.
I have since referred to this as “The Chicago Way.”
I’ve had many “Chicago Way” moments in my life—with my children, business associates, and other family members.
A few years later, I was trying to reach Stephen by phone and became concerned when he didn’t answer after several attempts. When he finally called back, he casually mentioned he hadn’t returned the calls because he’d been in Hawaii for a week. Oh, Chicago.
Then there were other moments—like when a hurricane was approaching Hawaii while he was living there, and I called, worried. Only to find he was on his way to Burning Man. Oh, Chicago.
It isn’t the Chicago moments themselves that bother you. It’s the moment you realize you thought you were playing checkers—and all of a sudden, the game changes to football without warning.
I wouldn’t have stopped Matthew’s or Stephen’s adventures. (Frankly, I don’t think I could have if I wanted to.) But I would have loved to be part of the discussion.
With kids, it’s part of the process. You almost have to experience the Chicago Way for them to become full adults—with independent thinking and actions. It’s painful at times, but I’ve learned to evaluate these Chicago Moments much like I do the City of Chicago.
There are moments when you find them in Wrigley Field eating a Chicago dog (Type A), and moments when they’re calling from a south-side precinct asking for bail money (Type B).
Type A is when they’re experiencing independent thought and taking chances—basically living their lives as functioning adults.
Type B is when they’re doing something they know is wrong and hiding the truth because they’re trying to get away with something.
There is a huge difference between A and B. Both are lies of omission, but not all lies are created equal.
I’ve found that understanding the Chicago Way has served me very well in business.
It’s impossible to run a company with 100+ people and 1,200 consultants and know what everyone is doing all the time. And every day, someone will surprise you—changing the game and doing something entirely unexpected.
As a manager, you have to decide: Are these actions Type A or Type B?
Surprises aren’t bad. But the ones done with intent to harm or deceive are the ones you have to eliminate. So when I’m surprised by new information, I first ask myself:
“Was this to help us, or help themselves?”
You want people taking chances and thinking of new and innovative ways to do things. But you don’t want people trying to rig the 1919 World Series.
A challenge in life is to create a world—both in business and at home—where people can be independent and honest. It’s too easy to tell yourself a lie, and many people live with the George Costanza philosophy:
“It’s not a lie if you believe it.”
In my favorite book by Dr. M. Scott Peck, People of the Lie, the subtitle is The Hope for Healing Evil. His central theme is that malignant narcissism is the root cause of evil. Doing what you know is wrong, then hiding it by omission, is never justified—and is at the root of destructive behavior.
Telling yourself that the ends justify the means fails when the ends hurt other people and take advantage of lies for your own self-interest.
We have to create environments where we’re not being clever and deceitful—but living with openness and honesty. There is plenty of room for unannounced trips to Chicago and Hawaii, and every thought does not need to be shared.
(Trust me—we don’t want Matthew sharing his deep, dark secrets with anyone.)
We just have to be sure our trips to Chicago are not to hide unpleasant truths, but to have privacy and personal adventures. The Chicago Way can be a pathway to great adventure. It’s doing it for the right reasons that makes all the difference in our lives.
I’ve been to Chicago quite a bit myself—sometimes to enjoy a baseball game, and sometimes to hide.
I regret the hiding.
And I enjoyed the Cubbies.
Our lives can have both wonderful secrets and great shared truths. The success in life is making sure your trips lead you to where you want to go. The secrets should become things to celebrate when it comes time to reveal them—not things to be ashamed of because of the people they hurt.
So take your trips to Chicago. Just make sure they end in a story you’re proud to tell. And yes—Go Cubs.
Love, Dad