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Maybe Rachel Shteir Was Right

Oprah Winfrey

Update (12/2/13): This was a hard post to write, because I felt kind of heart-broken writing it. I love Chicago, and yet as we all know, that’s sometimes not enough to sustain a relationship. I wanted to add a note here to honor how many other people–both fellow Chicagoans and former Chicagoans–have been finding meaning in this post today. Thank you for reading it, and if you have anything to say, please do leave a comment.

Update (4/10/14): The other shoe finally dropped four months after I wrote this post. Today, as I announced elsewhere on my blog, Ryan and I have decided to move to Los Angeles. In the end, I really have come to believe that Rachel Shteir was right.


I’m coming to understand what fellow New Yorkers told me before I moved here, and what fellow Chicagoans have been telling me ever since. No matter how much you may love it, there is a reason people leave Chicago. Except for summer 2007, when I almost moved back to NYC and then at the last minute decided not to, I’ve spent the past eight years of my blog loving on Chicago. But I have a feeling that love affair is over.

Last week I noted that Ryan and I have been considering moving away. We’re strongly considering Southern California (which anyone reading back in April might have figured out.) But other large urban places have been on the table, too, including Washington, D.C., San Francisco, and even a parting glance back at New York. While we haven’t made our minds up yet, I wanted to examine why we’re feeling not so sweet home in Chicago anymore.

It certainly came as a surprise to me. As I wrote last week, the unexpected pause in our usual activities (work and study) opened up a lot of room to consider where we were in our lives and, more importantly, where we wanted to be. So how does that lead to maybe leaving Chicago?

Many people have written about talent-drain from Chicago. Leading urban analyst Aaron Renn has covered the issue on his blog, The Urbanophile, for years, and in summer 2012 in a widely read City Journal piece (The Second-Rate City?) zeroed in on two big reasons why: entrenched interest groups that benefit from the status quo; and the lack of a true, world-city wealth-generation sector or industry. Earlier this year, Rachel Shteir, in her now-infamous book review in the New York Times, stirred great controversy for suggesting (as Renn did a year before she did) that Chicago’s civic boosterism might be laid on top of a far less secure social and economic base than the city’s political and foundation leaders might suggest.

Shteir made her comments as a 13-year Chicagoan. Renn (for full disclosure, a former client who didn’t get as much out of me as he should have at the time) made his comments as a former adopted Chicagoan. Born in Indiana, this city seemed to hold the potential for personal greatness for someone who loved cities that way that he does.

He lives in Rhode Island now.

I don’t pretend to have the analytical grasp of this town that these two do. But for almost eleven years I’ve wondered why living here often seems like living in very well-meaning molasses. Want a city where the hiring process takes months and mission-critical jobs are left unfilled for eons to make sure HR vets the absolutely perfect (read: cheapest, least likely to leave) candidate? How about a city where the leading local newspaper can never get the locations of the city’s own neighborhoods right? Or for that matter, a breaking-news cycle that doesn’t bother to actually break news any earlier than the evening newscast unless it involves weather?

Perhaps you’d like a town where the civic leaders who live here don’t bother to actually send their kids to the city’s own public schools? Or where the people who sit on the boards–and in the executive offices–of the local public transit agencies don’t actually take public transit themselves?

Or maybe you just want to live somewhere where it’s becoming the norm for leading nonprofits to offer, with a straight face and in all seriousness, $30,000 annual salaries for mid-career, middle-management jobs? Except that those jobs are now retitled as less-than-management in order to make those salaries somehow look more human? Much less reasonable?

I love Chicago. Not one day of the past decade that I have lived here have I ever felt that I left anything behind in New York City. The alternative list to the above–the list of things to love about this place–is actually much longer. We have the friendliest urban population I have ever encountered anywhere on earth, a world-class restaurant scene, world-city caliber museums and performing arts, an urban lakefront envied by every other city in the country, and–although the natives don’t believe it–dirt cheap rents and housing prices compared to our peer cities on the east and west coasts.

And yet, we also eat our young and that breaks my heart. A decade ago, people outside and inside this city told me how Chicago cannot hold on to talent. How, in order to really achieve success, you do your time in Chicago, and then you leave it behind. All these years later and I have my own stories of watching a steady stream of professionals, artists, planners, techies, plain-old joes and janes, and more than a couple of terrific rabbis–some from here, some from elsewhere–embrace this town with all their hearts and then say good-bye and thank you, and leave.

Our weather and the nepotistic Second City-SNL one-way trip to New York notwithstanding, I fully believe many of the people who leave this place don’t really want to. I’m not so sure Chicago can’t hold on to talent. I think more properly, Chicago refuses to hold on to talent. Maybe it’s the alleged lack of a wealth engine, or the very real post-Great Recession lack of endowment money. Or maybe it’s the “entrenched interests” holding on to the status quo and driving costs up and opportunities down for everyone else.

Maybe it’s all those decades of living under the practical empire of a corrupt political machine, outdated by more than a century in our peer cities, that taught–and still teaches–people not to rock the boat and to simply be happy with what they have, to revel in “regular”, ordinary lives, as Shteir puts it, and not to bother to strive for anything greater than the middling roles this city seemingly preordains for people who aren’t members of the local ruling classes. Or maybe it’s just a chicken-and-egg thing that has no real answer–Chicago lets people leave, because people are going to leave anyway, because Chicago lets people leave…

Whatever the reason, it’s a given in this town that if you are very good at what you do, and you’ve got an offer from another employer, you can pretty much count on not being countered. And if that job offer is from somewhere outside Chicago, you might as well hire the cross-country movers the day the offer comes in. No one will keep you here. It’s kind of the grown-up business world version of the hoary, old knee-jerk reaction by Chicagoans to hearing criticism of this place: if you don’t like it here, you are welcome to leave. Chicago isn’t changing just for you. Or really, at all.

Over and over and over, even if that means that Chicago is losing out by being paraochial and stubborn. In the latest awesome example, the Sun-Times just lost its social-media honcho, Marcus Gilmer, locally famous for editing Chicagoist and the A.V. Club, to the San Francisco Chronicle. How? The Chron saw what Gilmer was doing in Chicago and created a new social media job for him in the Bay Area to entice him to go. And go he will–because somehow in Chicago recognition of talent by our peer cities means, somehow and sickly, that you’re not worth holding on to in Chicago.

I never mourned New York City. I left my hometown and I rarely looked back. In more than a decade, I can count on one hand the number of times I’ve actually physically been back. I miss people, but other than friends the only thing I ever felt I truly left behind was Portuguese restaurants. Meanwhile, in 2007 I cried and cried at the prospect of leaving Chicago.

That hasn’t changed. In a manner I can’t explain, my heart lives here in a very tender, very real way. But at this point, I feel like the passionate love affair I had with Chicago for so long has in some important ways run its course. It’s like coming to the opposite end of a 25 year-long arc of my life. In my late teens, I decided to go to college and grad school to be an urban planner. I eventually ended up in the city considered to be the birthplace of the planning movement. But I haven’t been a planner in a long time. And I fear that I’m coming to see that the price of living in America’s warmest, friendliest big city is checking your career aspirations at the city limits.

I left New York because I needed to explore the social and the spiritual aspects of my life. Now, I think it’s time to let the pendulum swing back a little in the opposite direction. Personally, I’d like to live in a city again where if they want you, they hire you on the spot without deferring to an artificial waiting period put in place by a bloated Midwestern HR department trying desperately to justify its existence in the org chart, and where if you’re good, you’re asked to stay, not given a going-away party.

No hard feelings, though. This place is awesome, and if I do happen to leave it, I’ll be an emotional wreck in the process. I grew up here, in a sense. Leaving here would feel a lot more like leaving home for me than leaving New York ever did.

But I’m not knocking myself out to feed the status quo here anymore, either. Chicago, we had a really good thing. But you make it hard to love you sometimes. As local blogger Ana Fernatt wrote in July while she was considering leaving, you’ve been my baby for years, but you really need to pull yourself together.

So for now, let’s just be friends.

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Mike Doyle

I’m an #OpenlyAutistic gay, Hispanic, urbanist, Disney World fan, New York native, politically independent, Jewish blogger in Chicago. I believe in social justice, big cities, and public transit. I write words and raise money for nonprofits. I’ve written this blog since 2005. And counting...

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24 replies

  1. This article is fantastic. Having grown up all of my life in Chicago, I can say that people really are interested in being content. Rocking the boat is a no-no and that is probably a reason why politics is so crooked (and not the cause). If people changed to more of a progressive attitude, they might be able to get more out of the political institutions that serve them.

    That said, I am a business person and am interested in starting my own business. The idea of devoting myself 110% here seems a little out of place and I seek to be around a culture where people are a little bit more gung ho about reaching excellence. It is amazing how many great entrepreneurs left the city: Ray Kroc, Walt Disney, Hugh Hefner, Larry Ellison, etc. The likes of Yelp or Youtube or Netscape, started at the Univ. of Illinois, did not come to Chicago to succeed, which would have been the more geographically practical choice. Groupon, the flagship Chicago startup, is something of a joke.

    It is a strange thing, but the city is not really that ambitious.

    1. Thanks for your comment. I think it’s a chicken and egg kind of thing. Are the people not ambitious because they can’t rise on their merits due to political patronage running the state, or does political patronage run the state because the people aren’t ambitious. It seems to me, you have to be taught not to be ambitious. I think the politics here beat ambition out of you.

      Although to be fair, Walt Disney left when he was four. 😉

  2. I honestly can’t take anyone seriously who thinks of Aaron Renn as a serious urban thinker.

    I grew up on the West Coast and have lived in Chicago for most of the past 20 years. While I’ve not (yet) become a millionaire, I’ve achieved enormous opportunity here that would have been possible other places, but at a much higher personal and financial cost to myself. I earn good money here and I get to live a very nice life with it. I’ve looked at moving to New York or San Francisco or Los Angeles and, frankly, the opportunities would only be better in San Francisco and the income would not match the increased cost of living.

    You appear to be making the same sort of lame excuses Renn made to justify his departure from the city – and I say with no malice that people who leave Chicago to settle in places like Rhode Island were probably never cut out to be city people to begin with. No city will be good at attracting people drawn to small towns and ageing rural manufacturing sectors such as Rhode Island. People who leave Chicago for a promotion to the New York headquarters are fundamentally different from people who leave Chicago to live in Rhode Island or Colorado Springs or Flagstaff. These are people for whom a big city is not their idea choice, and feeling bad that Chicago isn’t a small market is a fools game.

  3. Chicago is much more colder than the weather I just lost a 22 year old son to gun violence and there are no resources or help and the whole world is talking about the violence here in this World Class City and they have no clue or are unwilling to even try to help surviving families because Chicago Politicians and Police seem to open secretly like that Al Capone image “Like us or not, it’s ok to kill in this town” Chicago is Brutal it outshines the beauty they will use you up and try to suck the best out of you.I feel if Chicago treated Jordan and Oprah with an Open door policy my poor family never stood a chance there’s just to many generations of hand me downs from family to family those born here all agree you usually have to know someone to get a decent job and as diverse as this city is it is still the most segregated city in the U.S. i want to run from here but i have n’t the resources i wish i had some of Jordan or Oprah money i would leave for Midway or Ohare as i speak and no one would care or miss us because they are to busy trying to survive..

  4. This paragraph sums it up in a nutshell:

    “Maybe it’s all those decades of living under the practical empire of a corrupt political machine, outdated by more than a century in our peer cities, that taught–and still teaches–people not to rock the boat and to simply be happy with what they have, to revel in “regular”, ordinary lives, as Shteir puts it, and not to bother to strive for anything greater than the middling roles this city seemingly preordains for people who aren’t members of the local ruling classes. Or maybe it’s just a chicken-and-egg thing that has no real answer–Chicago lets people leave, because people are going to leave anyway, because Chicago lets people leave…”

    The UNDERLYING problem living Illinois are the politics. It has affected the citizens of Chicago/Illinois for the past century. The very thing that WE as transplants come to realize in time are the local governments (county, city and state) suppresses any sort of growth or prosperity and success. This IS main reason talent eventually leaves the state. We’re shunned away and the result of that is the city never has a chance to build a strong pool of talent within the vary sectors of the economy. We’re shunned away.

    I personally think the local governments prefer to keep things the way they are and the indigenous Chicagoan’s have been brainwashed throughout generations to believe the city/state has a concrete ceiling. If government would the talent, restructure the business climate and simply get out of the way, then individuals and businesses could/would flourish. We get tired of fighting the city and being controlled by the corruption.

    As this is happening, we lose our drive, we lose our dreams, we lose who we are as a motivated individual, we lose like-minded business counter-partners and connections, we lose our sense of purpose and we tend to fall into that brainwashed cycle that all indigenous Chicagoan’s know all too well. But aren’t aware of.

    Instead of continuing to live in a region that is stagnant and close-minded, we choose to relocate to another environment that embraces change and rewards success. I think many people stay here hoping things will eventually change only to be disappointed.

    I personally think transplants should get involved in local politics to bring fresh air to Illinois politics and I think it’s only a matter of time. If Chicago intends to support all of the posh apartments, restaurants and other attractions then they’re eventually going to have to bow down to all of these young successful’s coming into the city. They’ll eventually have to listen, otherwise we’ll simply pick up and move to other cities that promotes success.

    1. Thanks for your comment. My reply to Leah, above, covers a lot of the ground that you do here. I agree, the political power structure of Chicago makes it impossible for change to happen.

  5. Michael, as a 9-year Chicago resident and now living in San Francisco, I agree with the assessment of Chicago as feeling stagnant, and where people are content with being… content. I didn’t really realize it until I left and moved to SF.

    My experience is largely related to the startup world, and even in that fast-paced arena the differences between Chicago and other cities are apparent: SF startups strive to be big, to invest aggressively, build and grow quickly, build a base of users and then monetize. Chicago startups (with a few exceptions) tend to grow slowly, monetize early, take less investment capital, instead growing by investing the profits of the business, which allows them to grow and build on a MUCH slower growth curve.

    But even outside of the startup world, now that I have some distance I find Chicagoans to be — on the whole — just content with how things are, and “why look for more?”. They have their job, and their commute, and watching the game at the bar, and weekend softball, and they’re satisfied so what else do they need?

    But for people who want to do something great or different, they’ll quickly find that the general vibe of Chicago supports “stay where you are” instead of “really get out there and make something happen”. It’s no surprise that people who feel that drive find that they want or need to leave the city. I’ve talked to a few other people who have left Chicago, and the sentiment is the same.

    It makes me sad, but for this reason and the ones you outlined, Chicago really will always be a nice city, but it won’t be the world-class city it once was (or believes it is now).

    1. I think you really nail it in terms of the (let me coin a term) “happy rut” people get into here. No one will be awesome, because the system doesn’t want you to be awesome (because that would be a threat), but you do get to have a “good enough” life to keep you happy–which of course keeps you quiet and in line. I really don’t know anyone here who is from here who dreams of bigger things than they already have. I never thought about that before, but the only people I know who do dream of greater things are not originally from here. I think living here teaches people not to strive, since so often you get slapped down if you do.

      I would add, it’s very hard here to do progressive work. When you stand by your principles here in terms of justice and fairness, you often get black-balled. I was just having a discussion about this with a former Chicago strategist who left because the realized their ethical values were not supported by the democratic machine here. How sad is that? Things don’t change or improve here not just because people won’t get involved to change them, but because structurally, I’m really not sure that they can.

  6. Not to dispute anything you are saying – but I do want to point out something I’ve noticed is truly a factor in the music biz specifically – and may be more generally true.

    There’s a general belief that Chicago is part of “Fly-over country” and nothing of import happens anywhere except on the coasts. I don’t mean at all to complain that this is the entire problem – but clearly it’s also a factor leading to an “Inferiority Complex”.

    Speaking specifically of New York City – there’s no comparison to the Jazz Scene there as Chicago – or anywhere else in the world. LA has a movie and recording industries that dwarf Chicago. But looking at cities like San Francisco and Nashville – much smaller than Chicago – musicians there have an easier time getting national recognition than in Chicago without moving away. Some of it deservedly but not always.

    And then there’s New Orleans – which is a category unto itself on well level – but on another – nowhere outside of Europe do I see a civic recognition of the role culture plays in the city….

    On the technology job front – Chicago has always been stodgy – which has inhibited the whole “start-up culture” until the last few years. That has changed for the better – but still has a long way to go.

    Economically – I fear your comment about the $30K job offer is a sign of the times. I hope I’m wrong and it’s not the same elsewhere – or you can find great offers here and stay.

    All the best!

  7. I loved the article and think the writer had great points that he made about Chicago as a whole. I actually love Chicago and been there most of my life. If I was to ever go to New York, I don’t think I would completely put Chicago under the bus because it made me to the person that I am today. Taught me if you want something you got to go get it and hand outs are few and not what u need because u are strong and can make it. However, I dislike the fact that there are so few many programs to help those in need get back on their feet and crime has skyrocketed to the roof which is not the reason I left but encourages me the more reason not to move back in the city unless I can afford to move to a nice area far North. I left Chicago almost four years ago because I wanted to venture off a little bit and see what was out there for my son and I having left an unhealthy relationship with his dad and with no other options I chose to pack up my five bags w/ a ton of tax money and go see how Minnesota was really like. It was hard for me for a while in Chicago not because I didn’t not complete my degree but because I was having financial hardship and the job market of course was not great there and the politics has been corrupt well before I was born. However, the main reason I left is because I had no other choice so I took a chance and moved in with my Aunty and that was not easy but I stayed there long enough to get on my feet and been doing good ever since up here. Minnesota is a great state because they care about the family as a whole and will help those in need get on their feet. I am glad that I moved here but always there is something inside of me that wishes I was back in Chicago doing as good but Chicago makes it hard for people to make it, I guess that is just how the city has been designed since the beginning but honestly would I miss home and if things were the same here like there. I would move back but until then I will take my son to visit his dad and my family. Great article post!!!

    1. This. This nails so much of it. I’m glad you and your family found greater happiness elsewhere. If I leave, I know I’ll know the melancholy feeling of being emotionally tethered back to here.

      1. Hey Michael, thanks for the article and for commenting, I think about home a lot like Dorothy for the Wizard of Oz says there is no place like home. Yes, it is true but this is where God has me for now so this is where I will stay till he leads me elsewhere.

  8. Very interesting article; although you come from a different field than I do, I’ve always told people one thing when they ask what Chicago is like–it doesn’t change.

    Chicago, when I left 10 years ago, is almost exactly like the Chicago of today–although there are much better Craft breweries now. It’s a city of “institutions” (the Weiner Circle, Flat Sammies, Garret’s Popcorn) that are doted on by the locals religiously. And while it’s good to know that the things I’ve always loved will be there when I go back, it’s also disappointing in that things just don’t change. There’s a stagnancy about Chicago that I don’t relate to anymore.

    1. It’s funny, you’re right. I can think back to early 2003 when I arrived here, and compared to today in late 2013 the only things that have really changed are the CTA (for the better), the skyline (which has gotten even more crowded), and the mayor. Now that last one is particularly interesting. I always thought when the Daley dynasty ended, Chicago might embrace truly inclusive, vibrant local politics. Instead, it’s as if everyone just switched out the word Daley for Emanuel, and still speak of the mayor in hushed, fearful tones. Whether that means this is the state of civic being Chicagoans really want, or we’re just still living on auto-pilot from the Daley decades, I don’t know. But I do think there is an awesome well of fear in this city towards the idea of disagreeing with city hall or local foundations. It’s really sad, because without being able to–or choosing to–do that, nothing can ever change.

  9. Two things: first, there’s a big difference between people leaving for the suburbs and people going to other cities, and their reasons are generally different. Every big city has a steady outflow of young people leaving for the burbs. And we’re not the only town where rich people shun public transportation either. As for leaving to a different part of the country, part of that is certainly weather, and I can’t deny the appeal of California dreamin’ on a winter’s day. But that’s always been an issue for the snow belt, and always will be.

    Second, the grass is always greener. You’re hardly the only person to want to change scenery after a few decades. That’s hardly unique to Chicago either.

    Also (I guess this is more than two things), your experiences with HR people in your line of work (or whatever you were applying for) do not strike me as universal, or even typical, for Chicago, especially in “this economy.”

    1. Dan, thanks for your comment. I wasn’t talking about people leaving for the suburbs, but specifically about people leaving the region (Chicagoland) as a whole. The way that everyone here when they visit somewhere else just says they’re “from Chicago”? That way. I also don’t lay blame solely on the weather, or even primarily. I think the weather is simply one factor, because if you’ve lived here long enough for leaving to be a big deal, you’ve made peace with the weather already.

      Of course, having traded NYC in for Chicago in 2003, I would be the last person to suggest leaving one big city for another is somehow a thing unique to Chicago. I do, however, think the particular type of churn that exists in Chicago is very specific to this place. Specific enough for many, many people to remark on it, and to have remarked on it for a long time.

      I don’t know if you’ve looked for a job here recently, but my comments about job hunting, the candidate-search process, and bloated/lethargic Chicago HR departments not only describes what is happening now, but pretty much nails my past eleven years in Chicago. I am sure this city is varied enough for different people in different sectors to have different career experiences here. But I know lots of people who could write this same post based on their own experiences with no help from me. Something is broken here.

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