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How does the Midwest sell us on winter? | Here or There

By: Chris O'Brien

Let’s say money is not an issue. And you could move anywhere in the country. Anywhere in the world. You could wake up every day in Italy or never see snow again down in the Bahamas. You could go to places where the temperature is just the temperature; there’s no “feels like negative 15.” Go to a place where it always “feels like” a good day for the beach.

Where would you go? 

For me, even if I had unlimited options, unlimited Theres to choose from, I know I would ultimately stay here in the Midwest. I can say with almost one hundred percent certainty that I will spend the rest of my days here in Chicago (or maybe Northern Michigan). 

And I know, I know, people might say, “Well, you never know where life will take you” or “There could be an exciting opportunity somewhere else. Nobody really knows their future.”

But I’m pretty sure about mine. At least location wise.

The reason for this unbridled confidence? It’s simple: the Midwest is phenomenal at sales. To use an old cliché, they say the best salesperson “can sell ice to an Eskimo.” Well, Chicago, Michigan, Ohio, Iowa, Kansas, Missouri, they achieve this feat every single year. The Midwest has somehow convinced us that seven-month winters are actually a good thing. 

Here’s how it works. The Midwest sales and marketing teams slowly walk into the conference room. It’s the heart of January, everyone on the team feels dejected. Hopeless. They’re all wearing winter jackets indoors. One person is wrapped up in a blanket. Everyone can see their own breath. 

They hear laughter down the hall from the California and Florida conference rooms. For those teams, every day of the week is casual Friday. 

“Oh, oh!” someone from the Florida/California room says in a loud, excited voice. “We could start with a shot of the golf course, then pan out to the wineries and people on the beach and a couple holding hands riding horseback and somebody surfing and snorkeling and then more smiling families. Close with a beautiful sunset. We could get celebrities. Put in a Kardashian or two.”

“That’s it! Done! Everyone, take the rest of the day off. You know what, take the rest of the week off!”

The person in charge of the Midwest meeting is about to speak, about to rally the troops when someone at the table cuts them off. 

“Look, we’re screwed,” she says. “How can we convince people to live in the Midwest? I mean just listen to what they’re saying down the hall. Surfing? Napa Valley? Dip my toes in the ocean? We can’t compete with that. I haven’t even felt my toes since Thanksgiving! They’ve got sunshine; we haven’t seen the sky in two weeks. It’s over. You don’t see Antarctica panicking because they don’t have enough people. Siberia doesn’t worry about their lack of tourism. Let’s just accept what we are and move on. We’re too cold.”

“Look,” the leader of the board says. “We can either give up, or we can work with what we’ve got. We need to stay positive. We need to be ready to fight. We need to take the gloves off!”

Everyone around the table starts to take off their mittens. 

“I meant more of a metaphor; you know what, that’s fine. Let’s do this! Let’s hear some ideas.”

There’s silence for a moment before a shy person near the door speaks up. He’s looking at his feet the entire time. 

“What if we somehow like, I dunno, said snow was, um, like a good thing?”

“Great! Alright, let’s work with that.”

“We could tell everyone how Christmas just isn’t the same without snow.”

“Perfect! More. More ideas!”

The woman who spoke out at the beginning, let’s give her a good Midwestern name, “Catherine” rolls her eyes. 

“Why would people be upset not to have snow on Christmas?” Catherine says. “I have a cousin in Miami who celebrates Christmas with a bar-b-q on the beach every single year. It sounds delightful.”

“Oh, but it’s not the same.”

“So true. It’s not the same.”

“Not the same at all.”

Catherine scrunches her eyebrows together. 

“You’re saying ‘it’s not the same’ as if that were a bad thing?”

“Gotta have snow. Gotta have a white Christmas.”

“Maybe we could have Bing Crosby sing a song about it, make a movie too? How does he feel about winter?”

“Mutual I’m sure,” the leader says. “Jot that down. This is great, love the energy, love the vibes. But how do we market snow?”

“You could like roll it into a ball and throw it at your friends?”


“We could show people how to make these bigger balls of snow, and you could like stack them on top of each other. And then you could grab a carrot and some charcoal. Make a snowman. I feel like kids would love that.”

“Ha, bigger balls,” joke guy chimes in. The whole room snickers. 

“We could have people lay down in the snow and do a jumping jack kind of thing. Call it a snow angel?”

“Who would do that??” Catherine says. 

“Oh! I got one! This might be a little bit out there, but you know how they have water skiing in Florida? What if we did that, but on snow?”

“We don’t have any mountains?” Catherine says. 

“Eh, we’ll use hills. Or maybe just a flat stretch of land, call it ‘cross country skiing.’”

“That sounds miserable,” Catherine says.

“No, not at all. I think it’s a great idea. What else? What else?”

“We could go to a frozen lake, cut a hole in the ice, and go fishing?” GREAT! 

“We could emphasize to parents how cute their kids look all bundled up in coats and hats?” PERFECT! 

“We could fill up a hot tub with hot chocolate and sprinkle little marshmallows on top and tell people to hop in?” HEY, LITTLE BIT WEIRD, BUT WHY NOT! 

Catherine can’t take it anymore. She stands up and smacks her hand on the table. 

“Enough! Look, this morning I woke up, I went to my car, I literally scraped ice off the windshield with my credit card. Every time my dog has to pee, I have to throw on my coat, my boots, my hat, my gloves. And this is our lives every single fricken year! Every year from November to what, March? April? May? You can’t sell people on this. It’s impossible!”

“So, then why have you stayed?” the shy person sitting by the door asks. 

The room is silent until the conference phone buzzes. One of the remote employees has joined the call. 

“Hey, it’s Bill from Minnesota, sorry I’m late. My car wouldn’t start.”

“No worries, Bill. What’s the weather like up there?”

“Oh man, we’re looking at a balmy negative 12.”

Everyone mouths the word ‘wow.’ The phone buzzes again. 

“Hi everyone, Debbie in Wisconsin.”

“Debbie! I heard you guys got pounded with snow last night? How much?”

“Eight inches.”


“Yeah, took me about an hour to dig out my car!”

Catherine looks around and sees a new level of camaraderie in the room. People are on the edge of their seats swapping winter war stories.

She wasn’t sure why the memory came to mind, but she remembered way back in seventh grade sitting down at a cafeteria table, and these girls she never met before started sharing stories about their crappiest day or their most embarrassing moments. One girl shared the worst parts of her recent vacation. Until that moment, Catherine always thought you were supposed to be happy, all the time, that you never—under any circumstances—talk about the bad stuff. Just put on a smile and stay positive. 

She remembered how finally it was her turn to share. She nervously shared her best-worst story, and they all laughed, together. There was comfort in the suckiness. The last person at the table chimed in, “You know what, I’ve never really had that bad of a day before. Life’s been pretty good to me.” Everyone at the table rolled their eyes.

The phone buzzes again.

“Hey, guys, Robert down in Del Rio, Texas. Sorry I wasn’t here earlier. My kid’s been sick this morning. Ah, who am I kidding, I was out playing golf. But hey, that’s neither here nor there. So, corporate asked me to join your call, see if y’all needed help with ideas. Man, I looked at the weather map today, I hate to say it, but we’re 100 degrees warmer down here. Isn’t that something? Y’all should move down! Anyways, here’s what I’m thinking. You should just focus on the summer months in your ad campaign. Hide the winter. Talk about how great June and July are up north. How you can go sailing, and—”

Catherine looked around the room. Everyone was rolling their eyes. One person was moving their hand like a little Pac-Man mouthing blah-blah-blah. She looked next to her and saw the lift ticket for Boyne Mountain hanging from the zipper of a colleague’s coat. “Mountain,” she thought to herself, shook her head, and smiled. 

She was starting to have a Grinch’s heart grew three sizes type of moment. She could see her middle school table again. She could picture Robert from Del Rio, Texas, pulling up a chair. You know what, I’ve never really had that bad of a day before. Life’s been pretty good to me. She could feel the room turning against the fair-weather fan. 

“Hey, Robert,” Catherine said. “We’re actually right in the middle of something here. Could you put yourself on mute?”

The Candy Cane is the Most Festive Way

to Treat Heartburn

More Chapters from Here or There

This is Chapter 5 of the new book "Here or There." Stay tuned for more chapters. To order the full book, email our librarian at, ask your local bookstore, or you can order on Amazon.

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