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Greg Baugues

lives in New York and serves on the developer evangelism team at Twilio.

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The harder the conflict, the more glorious the triumph. What we obtain too cheap, we esteem too lightly: it is dearness only that gives every thing its value. Heaven knows how to put a proper price upon its goods.

- Thomas Paine

Chicago is a bipolar city. For six months, we hibernate. We endure. We struggle. And from Memorial Day til Labor Day, we celebrate making it through another winter. Festivals. Beer gardens. Movies in the park. Baseball. Beach volleyball. The lake front.

When I first moved to Chicago nine years ago, I hated the winter. Winter was painful for me. Physically painful. Emotionally painful.

I grew up in Indianapolis where you’re afforded more margin to not take the winter seriously. It’s a commuter culture – you get into your car that’s been sitting in a garage, drive to the plowed parking lot, and walk fifty feet to the front door of your office, grocery store, or Applebees.

In Chicago, you’re more exposed. Even if you drive, you probably parked overnight on the street, and you’re probably going to park a couple blocks from your destination and trudge through a quarter-mile of unshoveled sidewalks to get there. If you’re lucky, you’ve arranged your life so that you don’t have to drive much, but now you’re walking to the train and waiting for the bus and, for an hour every day, winter is actively trying to kill you.

I used to ride into work with Josh Golden, who started the web consultancy I worked at for shortly after moving to the city. And every single winter morning, I’d complain about the cold.

Josh grew up in Canada – a place where you have to take winter seriously. He told me that to get through the winter, you need two adjustments: an adjustment of gear, and an adjustment of attitude.

For the gear, I learned to treat getting dressed as putting on a suit of armor to go out to battle. Next to a good wife and mood stabilizers, long underwear is the third most important contributor to my general happiness during the winter.

So, you get yourself a heavy pair of gloves, and a hat that covers your ears. You layer up – long sleeve t-shirt, fleece or a sweater, and a well-insulated coat with a hood. Get a pair of waterproof boots, put on wicking socks, maybe two pair. You tie a scarf to protect your neck, and on the really cold days, you pull it over your mouth so you can still breath.

And then you go make winter your bitch.

In warm climates, it’s too easy to take shit for granted. But in single digit temperatures, six inches of snow, and blinding, breathtaking wind, going to the grocery store becomes a worthy accomplishment. If you can manage to leave the house, make it to work, and feed yourself in the middle of a Chicago February, that’s a day you can feel good about.

This has been a particularly tough winter. When it started, we’d look at the forecast and say, “Oh man, it’s going to get down to single digits next week…” Now, we just call those days “Wednesday,” and we’ve still got three more months to go.1

In his 2008 essay on Cities and Ambition, Paul Graham wrote:

Great cities attract ambitious people. You can sense it when you walk around one. In a hundred subtle ways, the city sends you a message: you could do more; you should try harder.

The surprising thing is how different these messages can be. New York tells you, above all: you should make more money… What I like about Boston (or rather Cambridge) is that the message there is: you should be smarter…

As much as they respect brains in Silicon Valley, the message the Valley sends is: you should be more powerful… The big thing in LA seems to be fame… In DC the message seems to be that the most important thing is who you know. At the moment, San Francisco’s message seems to be the same as Berkeley’s: you should live better.

Chicago was absent from Graham’s musings, but I propose that her message is: “You should earn it.”2

There will be a day soon in March or April when temperatures will rise to the low 50s. The sun will shine, the snow will melt. It won’t last – it will be just a glimpse of what’s to come later on in May or June. But on that day, Chicagoans will emerge onto the streets and strangers will high-five each other, rejoicing in the reprieve from their collective struggle. In San Francisco, it would be just another Wednesday.

We earn our summers here. Every sunny day above 70 is so much sweeter because of the frigid grayness that came before it. There is a cost of admission to be a citizen of this great city and Chicago knows how to put a proper price upon her goods.3

To borrow from JFK, we choose to live in Chicago not because it is easy, but because it is hard.

  1. NPR: Just How Bad is this Chicago Winter? 

  2. This jives with Chicago’s tech scene which seems better suited for bootstrapping than for accepting large sums of money for revenueless webapps. 

  3. Rachel and I moved this year and found that rent had jumped 20% in two years. I partially blame our recent mild winters and am hoping that this year’s brutality will stabilize rent via lowered demand. There are people who, because of this winter, will leave Chicago and never live here again. 



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