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After living in New York City for 26 years, I got a dream job in Chicago that I simply couldn’t turn down. I wasn’t sure what the move would entail—my initial associations with Chicago having to do with Al Capone, the Bears, house music—but some preliminary Google searching assured me that Chicago was simply a “smaller, cleaner, friendlier version of New York.” Across the blogosphere Chicagoans compared their city to New York on nearly every level, from neighborhoods—Pilsen, the new Williamsburg—to amenities—if you like Per Se, you’ll love Alinea.  Deeper Web searching yielded even bolder claims to the ways “Chicago is infinity times better than NYC,” “kicking New York’s ass.” These claims rested on the premise that Chicago offers pretty much everything NYC does but without all the stressors. Or, as one blogger put it, it’s “NYC Lite.”  What New Yorker wouldn’t love the Big Apple scaled to size and rendered livable?

My first week in Chicago, I was eager and ready to take a bite out of this new apple. Back at home, I’d loved cocktail lounges with a secretive feel, so I sniffed out Chicago’s parallels. But things here immediately began to go wrong. Showing up at the doorstep of one such lounge left me bewildered. Why were they letting absolutely everyone in? Why were they closing so early? Where was the concept fashion? Where was this, where was that?

A wall of differences between the two cities pressed in on me day after day, week after week, regarding nearly every aspect of Chicago life. Continued let-downs left me deflated. One full year here I set out at 11:00 p.m., as I used to back in NYC, for a few hours of late-night midsummer strolling across bustling urban landscape. Forty minutes in, thats it. I stopped short on a corner. I was done. As beside me a Chicagoan beamed with pride before his downtown Chicago skyline, I hissed, “It’s not New York,” and cabbed back home to bed.

At some point I realized that on a basic level I was, as if seeking a former love in the arms of a new acquaintance, still looking for New York. And I think that this expectation arose precisely from the claims I’d encountered concerning Chicago as a “smaller, friendlier, cleaner version of New York.” Why couldn’t I just experience Chicago on its own terms, allowing its charms to irradiate my mind and imagination as New York once had? The charms were all there before me. Why couldn’t I let them shine in?

Having lived here for six years, I’d argue that the most apparent similarities between the two cities—“skyline, architecture, food, setting”—eclipse precisely the things that make Chicago so wondrously unique. What’s truly here in the guts and soul of this city, and where might we find it beyond the shadow of “Second City”?


In 2010, I prepare to attend a downtown Manhattan soiree. There will be a New York Times music critic as well as a Booker Prize-nominated writer, so I spend the previous weeks frantically researching music charts and poring through as many book reviews as I can cram into late nights.

Arriving at the party at midnight, I rock up the industrial elevator shaft and step out into the loft, model on my arm. We are the first people there, and, feeling naked now despite the low lighting, I jolt my date into conversation. Around 1:00 a.m. a crowd starts forming, the music critic and novelist finally appear among the socializing faces. We get within enough proximity to each other to broach conversation. One of them invokes an esoteric music album, and I stutter, “Oh yes, that . . . that . . . 1992 sophomore album was transcendent!”

And now the writer: Had I read that novel that hits stands next week?

“Of course I’ve read it already. Who hasn’t? Simply transcendent!”

Suspecting fraud, he presses me, quoting his favorite lines. I nod. I nod. Can he smell the dew swelling under my collar? “Sublime. Yes, s . . . sublime.”

He asks my thoughts on an obscure plot detail. I stammer incoherently. His gaze bores into me. A beat, then he’s away.


Now I am at a soiree in Chicago in 2015, celebrating a Hyde Park intellectual who until last year had his own radio show on NPR. Chicago intelligentsia, denizens of the art world, create buzz about the room. Around 9:00 p.m. as the guest of honor shakes my hand, I frantically call to mind the archived radio shows I’d studied the entire previous week in preparation. He preempts me with a smile. “Hey I heard you got that article published on education and race. Congratulations! I’m looking forward to reading it!”

Is he mocking me?

I hesitate, but find something curious happening. A doorway opening; a space emerging to talk about the writing life. Its struggles, its realities. He offers lucid advice, without judgment. We gab on easily about our children, his life after NPR, and the church we both began attending last year. I feel a thaw taking place in the air about me. A moment of wit and a burst of laugher and—for just a second—I forget where I am.


In 1952, A. J. Liebling unleashed a haunting spirit upon Chicago, naming it “Second City” and fating it to wrestle with the idea of “New York” as the looming standard against which it is judged.  Chicago defends itself from such “savage” criticisms, insisting on the ways in which NYC remains dirty, rude, nasty, snobby, unaffordable. Meanwhile, New York glances back with raised brow, responding, as Rachel Shtier did in her 2013 New York Times article, with chilling laughter. It becomes a never-ending co-dependent relationship. But zooming out, one finds the greatest American cities asserting their identity without anxious preoccupation with other cities: Portland’s hipster quirk, Charleston’s southern charm, Nashville’s country music, Louisville’s barreled whiskey, Miami’s beach glam. What about Chicago? Just another “smaller” and “cleaner” New York? How might we envision this city apart from the long hard shadows cast from the coasts, empowering it to emerge beyond “Second City” and “Third Coast” into its true identity as our country’s spiritual center?

I myself am beginning to put my finger on the pulse of it—this that Chicago has yet to name for itself and live into—and I must admit I’m beginning to fall in love.


Erick Sierra's photo

Erick Sierra resides in Pilsen and is a contributing writer to “Cult of Americana.”  


  1. Amazing story! I can see your idea behind people’s “unmindful” comments about New York when making a comparison with Chicago. I have also read your “Unforgetting 1980s Williamsburg, NYC” blog and I found the ideas behind these two blog posts very similar to each other. I appreciate how you address the diversity issue with some of your small stories. They tell a lot about what is happening today in this country. For instance, you mentioned above how some people describe Chicago as smaller and cleaner version of New York. It reflects how they stereotype not only certain group of people, but also places! Personally, I notice that those comments are becoming almost “acceptable” in today’s society although they are inappropriate and offensive. Here is another example from your “Unforgetting 1980s Williamsburg, NYC” post. The two ladies who said “Nobody used to live here” are the perfect examples of how people stereotype and exaggerate situations today. Again, causal comments can cause harm to other people.
    Recently, I had the honor to hear your speech at the Seaver Graduate Fall Colloquium & Dinner hosted by my school, Pepperdine University. I agree with your point of view on diversity. As an Accounting major, I believe that the idea of diversity directly affects people’s decision making in the business world. For instance, promotion and recruitment might base on one’s ethnicity, cultural background, and similar values. Furthermore, some companies even alliance themselves with certain characteristics. One good example about how a company can falsely promote itself in a negative way is Mike Jeffries, former CEO Abercrombie and Fitch, stating “only good looking people” are suitable for A&F’s clothes. My questions are:
    To what extend, do you believe that the idea of diversity affects businesses?
    Do you believe one should “shake off” the identity (or stereotypes) given by the city where one is from? What approach should he/she take?

    Comment by Paul Wong on November 1, 2016 at 12:24 am

  2. Hi Dr. Sierra. This article is really interesting to read, and you are an absolutely excellent writer. As you talked in this article, you felt disappointed about living in Chicago at very beginning after you move there from New York, and then you gradually fell in love with it. I really resonate with your experience as an international student. I came to Indiana from my hometown, China, for bachelor degree five years ago, with high expectation and hope for fabulous life in US. Yet, similar to your feeling, I felt that things in this new living environment were not as good as I expected. I am not accustomed to food here. The small town I lived in is much quieter than China. The huge difference of culture between these two countries made me deflated. However, gradually, I found lots of beautiful things here, like people, the most wonderful one, and got used to this new culture day after day, then I began to love the life here.

    I believe that both background and education shape our ways to think and behave in the daily life. The culture in our hometown definitely play quite important role in growth of our mindset and the way we live. For instance, New Yorkers getting used to enjoy themselves in the bustling street at night may not like the quiet night at Chicago. On the contrary, people from Chicago may prefer quiet night unlike New Yorkers. There are no absolutely good or bad things. We always unconsciously judge something different from our own perspective when facing with new environment and culture. It is hard to stand on others’ viewpoint to look into the problem.

    I have traveled to both Chicago and New York. I felt they are totally different identities even though many apparent similarities between them as you described. I totally agree that it is not fair to assess a city with preoccupation with other cities. I believe that Chicago has its own identity, rather than “another smaller and cleaner New York”. Different people view these two cities differently. It is difficult to change others’ different perspectives. It does not really matter if Chicago has to be given a name as Portland or Miami be like you mentioned. Its particular identity is still over there despite of controversy of “Second City”. People who fit in Chicago’s culture will really feel this city and see its identity.

    Comment by Wenxin Lin on November 9, 2016 at 2:14 am

  3. As a person who is studying abroad in America, I have gotten the chance to explore and to live in several different cities at different times. I have actually experienced the same thing you described in this article. Coincidentally, the first big city I explored when I first came to America was Chicago. Al Capone did make this city more intriguing to me, and while I loved all those gangster movies about the prohibition era, I still could not stop comparing Chicago with the big cities in China. The lifestyle, of course, is different in various places, and that leaves an imprint on the city. But the one thing I expected of any metropolitan city was some form of nightlife. In Asia, there are always plenty of places to eat at 2 or 3 am, all kinds of restaurants and night markets; the streets are very vivacious even at midnight. However, in Chicago, it felt like the city fell asleep too early, at least, from my hometown’s perspective.

    After spending two years in America, after traveling to many different places, meeting all kinds of different people, my state of mind has begun to change. Thanks to all the individuals who had certain stereotypes about me and all the people and places I had stereotypes toward, the chain that locked up my mind was finally broken. I realized that stereotypes are awfully wrong, and when you look at things with preoccupation, you miss the beauty of differences. When I finally started to accept the difference, I began to look at things from a brand new perspective. I now appreciate the differences of every city and every culture. Just like the quote you mentioned during your speech at Pepperdine University, “deep inside you, there’s a part of you, the most inner part, entirely free of disease,” I firmly believe the good inner part can be brought out of every person and every city.

    People are the key catalyst to that change, in my opinion. Just like you mentioned in your article that your feelings about Chicago started to change after you attended a soiree and met the guest of honor of that day, the people you meet at certain place do gradually affect your view about that place. Therefore, I could not help but image how much more beautiful we will find this world to be if only we could eliminate all the prejudice, if only everyone could see through Thomas Merton’s eyes, and we could all see the secret beauty of people’s heart. I certainly discovered more glamorous traits of different places and people after I stopped comparing and started to embrace their uniqueness. Just like my favorite quote from the movie “The Secret Life of Walter Mitty”(2013): “To see the world, things dangerous to come to, to see behind walls, draw closer, to find each other, and to feel”; hopefully, one day we will all be able to see what Merton saw in Louisville in the middle of an ordinary day.

    Comment by Qinwen Zhang on November 9, 2016 at 1:09 pm

  4. Hi Dr. Sierra, I really enjoyed listening to your talk at Pepperdine a few weeks ago! I hope all is going well with you. Your talk was truly insightful, and really got me thinking about how we as a people need to live in harmony despite our many differences. Living in LA has exposed me to a diverse populace from all walks of life. Yesterday, Ellen Degeneres said on her show that she “believe[s] we can all come together because if you take away the labels, you realize we’re far more alike than we are different.” While I am sometimes guilty of developing biases towards certain groups, I do also think that we need to recognize the intrinsic human characteristic within all of us.

    Last night, I found myself anxiously trying to keep up with updates from the election. In the moments leading up to Trump’s election, I noticed several things that just did not seem to sit right with me. My Facebook newsfeed was filled with bitterness from supporters of each party. Some stated that they were ashamed to be Americans. Many even looked into migration—so much so that the Canadian immigration website crashed. Riots broke out all over the country. This whole thing has been a mess.

    Amidst the chaos I recalled your interaction with your friend’s Trump-supporting father. It seems that many Americans feel the same way you initially felt after learning about his party affiliation—an immediate negative feeling towards the opposing party. I think some people may be getting carried away here. The important thing to know is that there is no turning back now. The people have voted, and Trump has been elected.

    While the President does hold a significant amount of power, America is not a great nation because of one person. It is great because of the millions of people. Rather than gloat or whine over the election results, Americans need to live in harmony and ultimately support their President. EVERYONE needs to accept and respect each other for who they really are. No matter what happens, the fight for human rights and equality will still continue. It will continue until there are no barriers between different groups of people. As we move on, we need to become a unified group to face our world’s more critical problems. There is always strength in unity, and it is vital that we can rely on each other as we face the obstacles that our future brings.

    I am really grateful to be able to apply what I learned from you to current events. Once again, thank you for visiting Pepperdine and sharing your work!

    Comment by Brandon Chong on November 9, 2016 at 1:57 pm

  5. In your article, “approaching the unthinkable thought of god”. You talked about the literature consider god as super-rational。This remind me of what we learned in the religious and philosophical foundations of ethics. However, I am going to talk about difference between Chinese and American ethic culture. In the U.S., The law is set up based largely on Christian, the people act with laws and Christian value. On the other hand, Chinese’s laws are set up mostly based on Confucius. There are basically three differences Comparing the U.S. culture to Chinese Culture.

    1. Faith in Christian VS Rationality in Chinese Culture.
    Faith means sure of what we hope and certain of what we do not see. Christian do not need to visually see the face of god in order to believe in god. This is faith. However, most Chinese were born to told there is not god in the world. In Chinese mind, we only trust what we see. There is no right or wrong to be a religious person or not. Suppose you are trying hard of your dream, if you are sure of your dream and hope, and you are sure you and your group could do it, you are more likely to be optimistic. You are less likely to give up because you are sure your dream and hope will come true. On the other hand, people do not have the religion could only think what they are doing is rational. What they are doing is right. But they are not sure if about the future and dream. Compare to Christian that have faith, people do not have faith are more likely to loss hope.

    2. Christian Trust compare to Chinese Cautious
    The beginning of trust: When the early Americans come to the new land, they know they have to cooperate with each other in order to survive. Trust is also based on the faith,trust is sure of other people overall will do good to each other. I have been staying in Midwest for 5 years. From what I saw in Midwest, American is a country based on trust. American’s law is based on trust; the most famous example would be the Second Amendment. American is the one of few countries that citizen could put a gun in their house. This is because Christian’s faith make Americans trust each other. Also, since American have trust, immigrants loves it and come in great numbers and boom the U.S. economy. However, in China, most people treat each other with cautious. When young people help old strangers cross the street, some old people could blackmail young people saying the young people make them fall down in order to get money from the young people. Also, helping a strangers take an eye on some belongings may result in a liability on the loss of anything inside. People might compensate for talking an eye on the staff because there is blackmail. Cautious also make Chinese have a skeptical mind, since Chinese do not believe the government, thus Chinese are more analysis more deeply and think throughout. Compare to that, most Midwest people are more kind, simple and trust each other.

    3. Difference between Confucianism Kindness and Christian’s love
    Most Christian I met are treat people with love. Christian’s love is from god, Christian think god love us and use Christian to love others. However, Chinese kindness is treating people good with self-discipline. One example of love is that Christian could help others without thinking about there might be risk of helping others and without asking for any give backs. Although not usually happen in California, but in most of the Christian community, Love is a voluntary help that do not ask for return, Christian get the love from god and help people actively. However, Confucius kindness is a passive love, that means Confucius teach people only help people if people are asking for help, which means most Chinese is not an active helper. This is because Chinese do not want to have the liability if the person receive help blame them for help. Chinese could be kind to each other but usually they do not help each other because they are afraid their help could hurt themselves. For example, Chinese do not want to help the refugees by sending troop because Chinese do not like to have the blame of not helping them well. What Chinese could do is to donate some money to the red cross. These problems lead Chinese do not help strangers they met and usually help the people who have relationship with them.

    When a person trust the people around him, love the people around him and have faith that his dream will come true, then he comes a small leader. When a group of people trust all the people in the world, love all the people in the world and have faith that we could make the world better, we are the leader of the world.

    Comment by NING WANG on November 9, 2016 at 2:14 pm

  6. Hi Dr. Sierra,

    I am a senior at Pepperdine University, currently taking Accounting Ethics, and I had the opportunity to listen to you speak a few weeks ago at a graduate student event. After listening to your thoughts on human biases and our altered reality, I explored your website and this article jumped out at me. After reading it I couldn’t help but see similarities in your experience discovering Chicago and the points you made during your talk about how we deal with other people.

    You first discussed how we all have preconceived notions about certain stereotypes by telling us a story about when you started talking to someone at a bar. At first, everything was going great and you made the assumption that he seemed like a decent guy; however, that all changed the moment he mentioned he was a Trump supporter. Then, all of sudden, everything you had initially thought about him was altered. You took every bad characteristic you associated with Trump supporters and began to place them on that one person. It was now as if you had a filter preventing you from seeing the real person in front of you, but instead, someone that just disgusted you and must have all the same beliefs as Trump and couldn’t possibly be a good person. I feel like this phenomena is exactly what happened when you first moved to Chicago. You went to Chicago thinking it would be just like New York and once you got there, you judged everything poorly because it wasn’t what you thought it would be. You were assuming the negative instead of embracing the positive. This tendency is very relevant in society today, especially with all the controversy surrounding the election. It is easy and natural to place people into a stereotype and make assumptions, yet difficult to keep an open mind and truly learn who they are and what they have to offer.

    Your comparison between the events in New York versus Chicago illustrate the idea that once stereotypes and preconceived notions are set aside, it is easy to see the truth. In New York, the city seen as a step above Chicago, the environment at the party seemed somewhat hostile, while the party in Chicago was much lighter and the people there seemed more genuine. I think part of that comes from accepting that Chicago isn’t New York but has just as much to offer, if not more. Once you stopped judging Chicago and assuming the experience at the party would be the same as in New York, conversation flowed better and became more personal. You talked about your children, the church you joined and realized that you forgot where you were. This supports your statement during your talk at Pepperdine that we need to dismantle judgment and align our loves and hates with God. Once we are able to think without judgment and embrace God’s will, we will be better people for it. This is especially important for society right now with everything that is happening with the government. I think there are many people that need to change their mentality and think this way in order prevent ongoing discrimination, which is still very prevalent today.

    Thank you for coming to speak to us. I feel that it was very thought-provoking and very relevant at this time.

    Comment by Esther Cha on November 9, 2016 at 2:40 pm

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