The Big Apple vs. The Windy City.

A few takeaways from a small town midwesterner.

The short painting of two magical cities — Artist: Barbara Below

New York City, home to nearly 8.4 Million and counting. Birnamwood-Wisconsin, home to nearly 800 and declining. Chicago, home to 2.7 Million and counting.

To me, while growing up in a small farm town, the community really had to work hard to provide for one another. Without a doubt being raised in a small town has helped influence me to find success in some of the most difficult cities to sustain work and life. Growing up in a small town in Wisconsin, I never saw myself living in New York City, where stores are open past 5 p.m. and inspiration as well as noise is on every corner. Now that I’ve made several big city moves, I couldn’t be happier with those choices.But growing up in a tiny town made me who I am and I wouldn’t trade my small-town experience for the world. Here are just a few takeaways I love being rooted from a place that’s population: 800.

The Windy City Vs. The Big Apple

It comes as no surprise that Chicago has had a chip on its shoulder since New Yorker writer A.J. Liebling deemed it as the Second City. I was able to spend several years on the grind of living in Manhattan prior to moving into one of the most beautiful neighborhoods in Chicago. Here’s to a few of the most influential, beautiful cities in America to work your ass off and experience life in your twenties.

  • Money talks
    From the beer you’re consuming to the apartment you’re stumbling home to after drinking that beer, everything’s relatively affordable for a city of Chi’s caliber. In New York a 240sqft, $1800-a-month studio is a STEAL. In Chicago that will get you a one bedroom, 24 hour doorman, gym, laundry, business center, and the best views of Lake Michigan.
  • Dinning
    New York has some fantastic restaurants, but best of luck getting into them. If you do get into them the price is going to hurt for a long time. Bring some New Yorkers to the Signature Room and the Hancock sometime and watch them get angry when they see how reasonable the bill is.
  • Biting the apple
    I must make note that New York is the most encouraging city I have ever lived in. Take a walk around any part of NYC and you’ll see people of all shapes and sizes, all religions and sexual identities, wearing whatever they please. New York seemed as though it was a world of it’s own constantly encouraging one to be themselves. New York taught me to be kind. The stigma that all New Yorkers are mean is beyond irrational to me. I had never been on a subway where someone else hadn’t given their seat to a pregnant woman, elderly person, or a child. People hold doors in the city, feed the homeless, and people overall are extremely generous to help strangers in New York City.
Central Park
  • Hitting the wind
    In Wisconsin I knew all of my neighbors and nearly half of the town was family of mine. In Chicago I had good — or at least pretty good — neighbors. We may have our occasional differences, but Illinois made out pretty well for it’s bordering states: there was the bland Iowa and Missouri folk to the West, the lovable rednecks from Indiana, and of course the beer cheese-loving college buddies from Wisco to the North. Kentucky was too far South it isn’t much of a concern. New York has New Jersey. Seriously, let’s move on.
Chicago River
  • Ball caps and Pizza
    New York has some great pizza, but its closed-mindedness holds it back. Deep dish for the win. In Chicago, we didn’t destroy our iconic baseball stadium. Bricks and bleachers make Wrigley Field, a temple in baseball. Yankee Stadium makes me feel like I’m about to watch gladiators run onto the field at the Colosseum, so pass.
  • The Hustle
    The hustle is real in NYC. I am still trying to catch up on sleep years later from the 70+ hour work weeks and endless late night bodega stops for bagels. I do indeed miss the bodegas. Chicago has space. Manhattan if you have a view of anything other than brick you are living upstate and that doesn’t count. Both cities create endless opportunities to be successful. They are breeding grounds for entrepreneurs, startups, and anyone who is curious and dedicated enough to follow their dreams.

I certainly have enjoyed life in both of the cities however New York is New York, and there’s no competing with it. But what you can get in Chicago that you cannot get in New York is continuous, high quality of life. Both cities have compelling theatrical scenes. In New York you have the home of Broadway, a $1.4 billion dollar industry last year, plus a thriving scene in every borough off Broadway. I must say Chicago is incredible for their comedy. “Second City” performers always come to New York when they are ready to be prime time players.

Here is the takeaway. Always be prepared and take risks. I learned very early on while living in NYC that you will get lost faster than NASCAR race. In a small town, you can always find your way around because you either run into someone you know or you only have a few streets to go through before you realize where you are again. A big city can swallow you up whole; I’ve definitely spent my fair share of time on the opposite side of the city than I was supposed to be. You learn quickly how to work your way around an unknown place. Getting out of my comfort zone after high school and moving into some of the most exciting cities in America has left me with some of the best experiences one could have.

With all of that being said, living in a big city is something I think every twenty-something should experience. You’ll learn how to stand on your own two feet, how to make a name for yourself, how to gain the confidence of being on your own, and the sense of pride from learning things on your own. You will make-new friends and explore uncharted territory. From the eyes of a twenty-something who has done the big city life, embrace the lessons you learn from a big city and enjoy every minute of it. Whether you want to find a place in the windy city or take a bite out of the big apple I encourage everyone to try. I will conclude this article while sipping on my cucumber infused water in my new city, the start-up capital of the world, San Francisco. I encourage all to experience a taste of these beautiful cities. Cheers!

Painted Ladies

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