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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