October 2015 will have been exactly one year since I moved from San Francisco to Chicago. There are many ways to describe this year — fascinating, exhilarating, stressful, inspiring, eye-opening, challenging, fun, fast, slow. I lost touch with friends and discovered which friendships can survive long-distance. I reconnected with old acquaintances who turned into friends. I learned what it means to work in a role where I have no local peers. I met an incredible number of entrepreneurs, business owners, and baristas (it’s what happens when you spend a lot of time at coworking spaces and coffeeshops). It’s been a roller coaster of a year.
One thing that’s for sure is I never expected to feel so intensely bonded with this city of Chicago. I liked this town when I was here in 2013 for a month. But I was not much more than a tourist then. I knew practically no one here when I made the move in October 2014. I was optimistic that I would enjoy this place. I didn’t realize just how much I would come to see the Second City as second to none.
A few months ago, I discovered a stunning album on Flickr on Chicago architecture and city life. Two entire hours passed with me in almost this state of trance, as I clicked through photo after photo of the El, of Marina Towers, of our river and lake, of summer festivals and snowed-in Winter Wonderland. These days, when the view of downtown opens up as I cross Wacker Driver on Michigan Avenue, as the lake shines in the sun as I bike along Lakeshore Drive, as I pass under the rusted elevated platforms of our train system, I feel this strong affinity in my veins. Even mediocre movies shoot to the top of my list when they’re filmed in Chicago. Greg Focker and Pam Byrnes are suddenly much more lovable just because they live in Chicago. Divergent would not be nearly as breathtaking without cinematic Chicago (even the dystopic version of it) as the backdrop. And The Dark Knight — well, that’s just an outstanding movie no matter what, but is there any city as perfect as Chicago for Gotham?
I moved here right at the beginning of winter. Best timing ever, as many people told me. My Airbnb host on my first night asked me if I had ever experienced a Chicago winter before. I said no, to which he encouragingly responded, “Oh man, you are DONE. You’re going to move back to California in a few months.” Thanks for the confidence, mister, and thanks for being so utterly wrong!
Between November and March, I used an anonymous Twitter account to document my observations and musings as a new Chicagoan. I knew that newcomers have a vantage point that no one else has. Newcomers notice things that are different and unique about a place, that others have become too accustomed to. I also knew that being a newcomer is a very temporary state of being, and that if I didn’t document my thoughts then, those thoughts were not going to come back. I am grateful that I did that. Looking back through that account now, a few tweets jump out. Not surprisingly, there are a lot of comments related to weather.
- Spend over half a grand on winter apparel, and that’s only part 1 of your shopping needs.
- There are companies here that help you find an apartment FOR FREE. Like, they do the work, and you pay nothing. We’re def not in SF anymore.
- It’s kind of a wonderful, wonderful feeling to walk from the cold outdoors into basically ANY store b/c it’s inevitably heated and cozy.
- Really starting to appreciate the power of a simple down vest.
- Okay I tried to be tough… but it’s time for two layers of pants.
- When your city smells like chocolate instead of garbage or urine… I think that’s worth a high five.
- Dunkin Donuts… your coffee is so good, but your food is so bad.
- It’s 52 degrees outside and some people are absolutely in short sleeves. Go Chicago. Also it’s supposed to drop back down to 18 tonight.
- 50s legitimately feels like summer. I mean, it IS about 50 degrees warmer than a week ago.
Many old friends have asked me, what do you like about Chicago? This is something I think regularly about, especially as it seems that somebody around me makes the decision to move “out west” almost every month, or at least talks incessantly about wanting to do so. During my first month in Chicago, I attended a local tech meetup. Everyone went around and introduced themselves. I told them I just moved here from San Francisco and was really enjoying this city so far. The meetup organizer exclaimed, “We got one back!” This led to a wave of laughter in the room that only happens when a joke is too real and too close to home.
I feel this deep, intense feeling toward this city because there is not one reason I like it. I like it on so many levels. I love the celebrity-chef good food and the regular good food. I love the local coffee roasters and the local beer breweries. I love the live comedy and the live blues music. I love the gorgeous architecture and waterfronts. I love that there are beautiful beaches in the city. I love the smell of chocolate in downtown, making my commute to work every day feel like I’m passing through a gigantic outdoor bakery. I love the crisp smell of winter air. I love the blue-collar history of this city. I love the abundance of great coffeeshops that have impressive tea selections. I love that it’s easy to keep my rent at a reasonable level. I love that people are genuinely so friendly — the stereotypes are true! I felt like such a jerk when I moved here. I was that person who didn’t start nice conversations with strangers in elevators.
But perhaps these are not that unique, compared to other major cities. New York City and San Francisco have good food, good entertainment, and pretty buildings too. I would argue that people are much nicer here than in the Bay Area and certainly NYC, but I acknowledge that’s subjective.
Maybe what turns these little things about a city into that intense feeling for the city is what I have become because of the particular combination of all these little things here. Because the city is so flat, because the lake is so incredible, and because (in the summer) there are literally five or more festivals every weekend (Rib Fest, Oyster Fest, Burger Fest, Beer Fest, Wine Fest, BBQ Fest, Sausage Fest, art fairs, music festivals…), I have discovered a love for biking that I had never experienced before. I had never hitherto spent so much time outdoors, among friends and strangers, exploring streets and neighborhoods across the city. I had never hitherto spent so much time indoors, among friends and strangers, feeling so much collective effervescence as we all cheer for the local sports teams while hiding from the cold in a cozy bar or restaurant. I had never, up to this point, enjoyed “going out to shows” this much as I do now when I spend evenings soaking up some of the best live blues music and improv comedy in the world. Spending all afternoon reading at one of the city’s many, many public parks had never been so appealing. Strolling through the city had never before been so fun, because there is so much here to see, so much here to do, so much breathtaking architecture, so many great restaurants, so much diversity from neighborhood to neighborhood, so much change in scenery from season to season.
The wide distribution of industries here means I am not always surrounded by tech people — and means I’ve gained a deeper understanding and appreciation for different lifestyles and life choices than ever before. In San Francisco, I always had this uncomfortable feeling that I didn’t belong there because the entire city’s socio-cultural-economic system seems designed around one pillar of power. And that pillar of power consists of young, male, white (maybe Asian) software engineers. They are the structurally protected kings of the city. Chicago (or Oakland, to some extent) does not have just one pillar of power. It has multiple pillars of power, and while a young, male software engineer might still have a lot of financial privilege, at least he doesn’t also have unquestioned social and cultural hegemony. Distributed power is a good thing for citizens. And distributed industries makes for a more stable economy (besides San Francisco, there’s another city that didn’t have great industry diversification — and things didn’t turn out too well for Detroit). One year in, I feel more welcomed as a Chicagoan than I ever felt as a San Franciscan.
The default friendliness of people in Chicago makes me more likely to engage with strangers. Last weekend, I had brunch with my Lyft driver. She and I got into a heart-to-heart conversation on the ride from my apartment to a brunch spot in Humboldt Park. She also told me the restaurant I was heading toward happened to be one of her favorites. When we arrived, she said she might come in to grab something to go. I invited her to join me for brunch if she wanted to. We ended up discussing education, politics, immigration, Mayor Rahm Emanuel, and the Chicago Public Schools system over rotisserie chicken, mashed potatoes, and collard greens. “I hope you don’t mind me crashing your meal,” she told me. I said, “No, this is what I like about Chicago — people are friendly here,” and I meant and felt every word of that.
This city has made me a nicer person. A more open person. A better person. A person who has rediscovered her love for trying new things. And yes, the winters are brutal — but in a way, I am grateful for them. They are, without a doubt, what keeps this city affordable.
Speaking of Mayor Rahm Emanuel and the Chicago Public Schools system — another thing I’ve come to appreciate about Chicago is that most people here love their city but do not confuse love with blind obsession. I once saw a poster in a local bookstore, in the form of a comic strip. In the poster, a man is complaining about Chicago’s weather, potholes, rats, crime, and other flaws, and the last part of the comic strip shows the man proclaiming, “I love this fuckin’ place!” Chicagoans acknowledge and vocalize the city’s issues, while still remaining the city’s biggest fans. People here don’t love the city blindly, oblivious or in denial or defensive toward its problems. I think it’s a stronger, deeper kind of love because people recognize those flaws — they know things aren’t perfect, but love the city anyway, and remain optimistic that things will get better. It’s no surprise there is such a vibrant labor movement and spirit of social activism here. It’s also perhaps why people here love the Bears and the Cubs and the Bulls so much, even though Chicagoans can go on for days criticizing Jay Cutler and recognize that they might live and die without ever seeing those teams claim a championship. People here wear the Chicago flag in more ways than I thought possible (on their hats, shirts, pants, backpacks, wall art, tattoos…) out of pride, without failing to see and discuss the shortcomings of Chicago Public Schools and the city’s racial segregation problems. Here, it is as writer and social critic James Baldwin says: “I love America more than any other country in the world and, exactly for this reason, I insist on the right to criticize her perpetually.”
Perhaps above all else, though, Chicago is a modest, hard-working city. Chicagoans put one foot in front of another toward their goals. There is little pretense or fluff. Under those seven layers of winter clothing are big shoulders and tested muscles. This is “The City That Works” indeed — in its past and in its present. Soon after I moved here, a well-known tech entrepreneur told a smiling crowd at a work event about this un-attributed saying: “If you want to make it in Silicon Valley, it’s all about how ‘cool’ your product is. If you want to make it in New York, it’s all about who you know. If you want to make it in Chicago, it’s about whether or not you actually have a business model that’s been proven to work.” I had several independent conversations in my first month in Chicago with people who have a lot of opinions about doing business in Chicago versus doing business in San Francisco. An app like Yo would never get any funding here, because what the hell is even the point of that app? Did you know some of the biggest exits in the past few years have been Midwest-based companies? You probably have never heard of any of them, because they weren’t in it for the mass publicity. And that was a common theme I heard from Chicagoans: people here work on businesses and projects that do something really well. They’re not here to be the coolest or shiniest or sexiest. They’re here to do the thing they’re doing really well, solve practical problems with their businesses, and serve whoever their clients or users are really well. And they grow and prosper because of the quality of their work, the usefulness of their products and services, and the soundness of their profit model. And Chicagoans are proud of this. Companies that are in it for the publicity? They should move to Silicon Valley, where they would probably do better anyway. It’s just a different philosophy. Instagram, Snapchat, and other money-losing ventures probably would never have succeeded here.
When I talked to people here about the fast growth of Chicago’s tech scene, the response is almost universally: we are so excited about that growth, and we want to make sure the growth reflects Chicago’s culture. We want our tech scene to be similar in size as Silicon Valley’s, but very different in nature. One of the favorite conversations I’ve had in Chicago was at a bar in the West Loop with my Airbnb roommate whom I lived with for two months. I told him we were thinking about hosting an event geared toward helping big companies think and act more like Silicon Valley startups. He said, “but don’t we have to ask why companies should act like Silicon Valley startups? Those startups grow and grow at the expense of so many important things. They are short-sighted and don’t take time to think about the long-term.” Wow, Alex. I think you have a point. It took some honest Chicagoans, like Alex, to make me look at the world differently. (Also, we had some great spicy ramen after that conversation. I think I mentioned earlier that Chicago has incredible food.)
So then why are so many people yearning to leave Chicago for the west coast? The three most common reasons I hear are: weather, terrain, and jobs. I fully acknowledge that one year in, I am probably still in a bit of a honeymoon phase with my new home of Chicago. All those negative-20-degrees days must get exhausting after a while. All those times when the Brown Line shuts down due to extreme climates must get irritating after a while. All that flatness must get boring after a while (unless you’re me — in case I haven’t said, I rather enjoy that this is the second flattest city in the country). At least three people I know who are on their westward way have cited the need for mountains as a reason for leaving. And if you’re someone who works in tech or wants to work in tech, there are still simply more job opportunities and more funding out on the coasts at the moment. I acknowledge that these are shortcomings of the city, and occasionally, I feel a dread that they will take me away from Chicago one day, too. What I can hope for at the moment is that before that happens, I manage to play some small role in making Chicago a more attractive place for tech-related talent. Because this city, in the grand scheme of things, is so very close to being perfect for me.
Okay, let’s wrap up this rambling piece of writing with some light-hearted talk, shall we? I am thrilled when people who live elsewhere come visit me in Chicago, because I love showing off my city and helping them fall in love with it too (which they inevitably do). Having lived here for a year now, and having had a visitor almost every month, I want to share what a perfect 3-day weekend or vacation in Chicago would look like from my personal perspective. This is my recommended itinerary for you if you come visit Chi-town and want to really pack in activities for your trip. If you’re looking at this and thinking, “there’s no way there’s enough time to do all that in one day” or “there’s no way there’s enough stomach to eat and drink all that in one day,” have some faith in yourself!
DAY 1 — DOWNTOWN:
- Breakfast at Beatrix or Bongo Room in downtown
- Coffee at Bowtruss or Intelligentsia
- Check out Art Institute of Chicago
- Walk through Millennium Park and take photos at the Bean
- Eat an Italian beef sandwich at Portillo’s
- Walk along the Chicago River, explore downtown architecture
- Take the Architectural Boat Tour
- Snacks at Glazed & Infused Donuts
- Watch the sunset and skyline from Museum Campus
- Dinner at Fleming’s Prime Steakhouse & Wine Bar (this one’s expensive)
- Catch a show at Second City in Old Town
DAY 2 — WEST:
- Food at Smoque BBQ
- Explore the lagoon at Humboldt Park
- Coffee at La Colombe or BUZZ: Killer Espresso in Wicker Park
- Browse Wicker Park — recommended: walk down Milwaukee Avenue, explore Myopic Books, check out Transit Tees for Chicago-themed items
- Lunch and hot chocolate at Mindy’s Hot Chocolate
- Ice cream at Jeni’s
- Explore Division Street
- Drinks at Green Street Smoked Meats in the West Loop
- Dinner at High Five Ramen, Girl and the Goat, or Sushi Dokku
- Catch a movie at one of those theatres with armchairs
- Vegan shake at Chicago Diner in Logan Square
Day 3 — NORTHEAST:
- Bike up northward along the lakeshore — enjoy views of the lake
- Breakfast at Big Jones in Andersonville
- Coffee at The Coffee Studio
- Explore Andersonville — recommended: check out interior design stores, visit Swedish bakeries, and browse Foursided for interesting gifts
- (If you’re feelin’ it) early drinks at Hopleaf
- Lunch at Crisp in Lakeview — Korean fried chicken and bowls
- Explore Lakeview and Lincoln Park — recommended: stroll through Oz Park, Boystown, and Wrigleyville
- Check out the gigantic Whole Food’s in Lincoln Park
- Dinner at Lou Malnati’s
- Drinks at Atlas Brewing
- Listen to live blues music at Kingston Mines and/or B.L.U.E.S.
Whatever you decide to do in Chicago, remember to bring a willingness to learn from strangers, a big heart, and an even bigger stomach. Bring a camera too, because this city is photogenic at every turn. And depending on when you visit… don’t forget to bring those jackets and boots. You’ll be surprised how good everyone looks even in winter gear.