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Vagabond Journey

Visting Chicago

Driving into the American dream.

CHICAGO, Illinois- I’d never really spent much time in Chicago before. I’ve actually never really spent much time in many US cities, besides NYC and Buffalo. My forays into American travel have usually been centered around going out into rural areas, small towns, and minor cities, using the metropolises more or less as logistical slingshots.

The layers of character that big American cities have always surprises me. They are like poorly re-painted walls: the previous colors still show through the fresh coats. There be stories here.

Chicago is one of those cities that you can really feel these stories. We stayed with my wife’s friends in the southwest of the city. It’s an area that could basically be called a black ghetto. High crime rate, boarded up drug houses, the corner liquor store is the social ground zero, tight knit communities where people smile and talk to each other — people who wave and say hello to benign-seeming outsiders.

The few times … well, the one time I’ve rented an apartment in a US city was in a place kind of like this. I like walking down the street and seeing people. I like talking to my neighbors. In the USA the degree of social interaction and wealth are often inversely proportional. Americans make money so they don’t have to talk to each other.

***
My wife’s friend is living her dream. It sounds kind of corny to put it in this way … but it’s true. She’s a baker and a couple of years ago she opened a cafe that became ultra-successful. Multiple movies, TV shows, and commercials have been shot there; the place ranks in the upper tier of Chicago’s culinary ecosystem. She loaded us up with truly exceptional food and coffee and set us on our way to the west of the USA …

But her story is ultimately straight forward: she actualized her passion, got really good at it, and went out and climbed the mountain. The story that I found a little more intriguing was that of her husband.

“I’ve always just taken the path of least resistance,” he summed up his life strategy. “I’ve never intended to be in the restaurant business.”

Apparently, he also never intended to be the director of pharmaceutical factories, the manager of research teams, or just about anything else he’s done. He just went out and let life happen to him: the perfect protagonist. He’s someone whose path ebbs and flows with change and chance, he floats on the river like a piece of driftwood rather than charging against the tide with a high HP outboard motor. He’s character who goes wherever the story takes him.

I asked him how this story began.

“I was doing a lot of drugs and I thought it would be cool to study chemistry in college.”

Then after he had a degree in chemistry it was only natural to get a job with a pharmaceutical company. This led to quality control projects which led to promotions which led to him somehow running a factory for GE … or something like that.

He was making good money with his job at the time which gave his wife the financial freedom to explore her passions. She started up an innovative catering business — which of course doesn’t make shit for money at first — but it gave her a platform to perfect her art and to learn the ways of the food business. She nailed it and in a few years found herself in need of a storefront to carry on the business. So she opened up the cafe. The cafe did well — so well that her husband’s once impressive income suddenly seemed a little paltry. Having the script flipped on him, he quit his job and joined his wife in the restaurant, where he is now running a crew of 28 employees at the apex of Chicago’s culinary scene.

Together, they were an ideal example of how the husband-wife partnership should function financially: one side working a mundane, decent paying job can allow the other to swing for the fences and chase dreams, which sometimes has the chance of paying off big.

My wife did the same thing for me when I was writing my first book — something that launched my career that wouldn’t have happened if she wasn’t working 9 to 5.

However, like most protagonists whose tales are intriguing enough to be retold, my wife’s friend’s husband wasn’t quite ordinary. He had a set of social skills that made him immediately likable and a competence that bled through his words. But he wasn’t threatening or intimidating. He wasn’t the type of guy that his inferiors would fear or his superiors would be threatened by. He was nice.

We often convince ourselves that the wolves get the meat. From my experience it’s not the wolves who really make it in business, but the nice guys — the nice guys that people like who make the people around them feel good. May of the CEOs, high-level managers, and company owners that I’ve meet while doing stories for Forbes who were truly good at what they did immediately put you at ease, they made you feel loquacious, they listened to what you said. The professional ascent of anyone has to do with other people selecting you from the ether — why would anyone choose to spend their days in proximity to a dick? Burn the Steve Jobs biography.

***
They can say no

An important lesson that I’ve been struggling to learn:

On the wave of the success of their first restaurant, my wife’s friends ventured into opening a second one — one that was almost guaranteed to be a success. They worked out a deal with the landlord, got set to dive in, but then halted: the week that these deals were coming together were hectic at the first restaurant — some workers were on vacation, others were calling in sick, they worked themselves ragged. “We can’t do this,” they said. “There is no way that we can add a second restaurant.”

So they said no.

I heard that story and I said wow. I’ve been having an extremely difficult time saying no to otherwise good opportunities. I say yes to them all and become so loaded up with work that it becomes difficult to do anything well. I’ve been professionally falling apart — I just can’t get the work done — and these past three months have been full of family obligations which I feel compelled to engage because they’re the “right thing” …

I need to say no … but after these next few months are over I’m not sure if there is going to be much left to say no to.

Filed under: Illinois, Road Trip

About the Author:

Wade Shepard is the founder and editor of Vagabond Journey. He has been traveling the world since 1999, through 88 countries. He is the author of the book, Ghost Cities of China, and contributes to Forbes, The Diplomat, the South China Morning Post, and other publications. has written 3411 posts on Vagabond Journey. Contact the author.

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Wade Shepard is currently in: Rochester, New York

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