Career ToolBox #47: Cleveland and Chicago – A Tale of Two Midwest Cities

I’m thrilled to be writing this column again. Thank you, Thomas, for saying Yes.

It’s been two and a half years since the last Career ToolBox article. Since then, I became a mom, released Date Your Career: The Longest Relationship of Your Life and, earlier this summer, my son and I moved to Chicago.

Living in Chicago has offered some insight about Cleveland. To look for work in Cleveland and, even better, to be employed in Cleveland, can be a far more rewarding way to live than to do so in a big city. Big cities by their own nature of grandness have greater competition. Back in June, a cool gig for a glamorous nonprofit in the 312 within one week attracted over 300 applicants.

I’ve seen my Chicago friends struggle. One local MBA who’s led at large global firms has applied to over 200 jobs. None has resulted in an offer. Another has applied to so many that he’s lost count.

There’s also the cost of living that fuels the Big City life. Yes, both Cleveland and Chicago offer incredible culture — art, music, theater, festivals, restaurants and events. But in one you can drive 20 minutes, pay $10 in parking and attend the local art museum for free. In the other you’ll spend over an hour in grueling traffic, pay $20-$30 in parking and then another $22 for admission per person. If you live out of state, you’ll pay even more.

When I made the decision to come to Chicago, I genuinely wanted my son and myself to not just spend more time with family but to also for him to experience that winning energy Chicago exuded in the ’90s, when it won six NBA championships, hosted the World Cup and the first (of many) Lollapalooza and launched the careers of Smashing Pumpkins, Liz Phair and Urge Overkill. In the metropolis of skyscrapers, Chicago was also home to Sears Tower, the tallest building in the world. When I left in 2001, Chicago was home to winners.

When I first moved to downtown Cleveland back in 2003, outside work hours and Browns games, the neighborhood was rather desolate. The “brain drain” discussion was prevalent. Fourteen years later? Fox News just published an article with the headline “Downtown Cleveland reaches 15,000 residents.” The 216 has emerged as world class, featured in publications both national and global.

On the flipside, I returned to Chicago at a time when Cook County property taxes are the highest in the nation, sales tax is 10%, there’s a (potentially illegal) sugar tax on sweet beverages and the state is broke. As result, companies are leaving. According to Atlas Van Lines annual migration report, “The study results released (in January) show that Illinois ranked third among all states in terms of the most outbound moves.” (

I’ve been thinking about what all this means. What’s the big picture, the theme, the macro-economic trend that can summarize this dichotomy, one of two Midwest Great Lakes cities that are just 350 miles apart from each other? And it all really boils down to one word: community.

Even 20 years ago in Chicago I never felt like there was a sense of community. Yes, there’s family and friends. There’s coworkers and perhaps some people you know that are doing cool, creative things in their spare time. Which with daily one hour to work commutes is a very short interval of real freedom. Life in Chicago for many is simply about paying bills. And all those taxes. And spending a lot of time in the car. And all that tremendous culture and architecture that Downtown Chicago is known for — glorious and gorgeous and grand? It serves as a rare escape, one that requires advance planning and budgeting and doesn’t forgive any level of spontaneous decision-making.

In Cleveland, it didn’t take me long to create a community around me. Dining with coworkers. Starting the local alumni association of my business school. Flying to Israel and befriending 50 people. The growing list of filmmakers. The CSU business students. Cleveland’s writers. Thanks to Deena Nyer Mendlowitz I even began to do public readings.

In some cases, people overlapped these different groups and if not, then I’d introduce them to each other and they would work on projects together. There’s an organic energy of growth and connection and helping each other. Even as a single working mom with an infant to raise, a company to manage, students to teach and books to write, a spontaneous text to join a friend for dinner, baby in hand, occurred frequently.

Without community cities perish. They become the lost Atlantis of a once-great civilization. I’m saddened to admit that Chicago is quickly becoming that Atlantis. The crime rates alone signal a broken community, one of desperation, anger and little hope. And those who live in million dollar homes in the North Shore are not immune. Most are just highly leveraged, desperately trying to design the best course for the next generation’s success path. So much about living in Chitown is about materialism. As one long-time and local friend so honestly put it, “Money is everything.”

I’m sure some readers, especially those who moved to or have roots in the 312, will be quick to object to this piece. Some will wonder what on earth any of this has to do with careers, jobs or resume advice. To all of them I say, everything.

I’ve shared with a few folks in Chicago how the last thing I’d ever want is to have a job that’s an hour away from home and with my son’s daycare another 30 minutes away and how proximity for all those three things is essential. And more than one person replied to me, “Well, lots of people do those long commutes. It’s just what you do.”

Exactly. It’s what you do in a city that, since the early 90s, began creating massive barriers to entry. Access to a good life meant moving to deep suburbs, especially if you had a family to support. In 2001 a $50K salary afforded you a studio in the city, assuming no car and zero debts. I know. I lived that life. At the time I could hop into a cab or on the el and be anywhere within 30 minutes. Today a studio in the same Lakeview neighborhood will run you $1000.

Cleveland is not perfect. Cleveland can learn a lot from Chicago on how to (finally!) develop its lakefront. And it could also use some new, unique downtown architecture and lower utility costs to attract even more businesses. Chicago is also one of the biggest destination cities in the country. Visiting Chicago is fantastic.

Cleveland has gotten a lot right over the past 10 years. In return for paying those city income taxes (which Chicago doesn’t have) you get so much more in return. You get access. You can quickly find your tribe, all the while discover new places and new talent. You just have to be curious.

As you consider where your or your kids’ next job hunt will take place, of course encourage yourself and them to move to new places and try new things. Seeing how the rest of the world works is a lifetime game changer. It’s what opens our eyes and makes us better.

Chances are they will eventually return. Because Cleveland’s gravitational pull is bigger than any big city out there.

It simply creates community like nowhere else.


Alexsandra (Alex) Sukhoy, a globally networked creative and business professional, is founder of Creative Cadence LLC. Her career coaching and marketing skills have resulted in numerous success stories for her clients. Her 5-Star business book, Date Your Career: The Longest Relationship of Your Life, is now available on Amazon, in paperback and Kindle. Follow Alex on Twitter: @creativecadence

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One Response to “Career ToolBox #47: Cleveland and Chicago – A Tale of Two Midwest Cities”

  1. Greg Coloian

    Touche Alexandra, I too was fortunate enough to move to Chicago in 1996 and live there for ten years. It was during the same fantastic stretch that you cited. But I came back to the CLE for family and friends. The one advantage that Chicago has is that it dreams BIG. CLE fights itself with people who don’t step down and don’t deliver. BIG ideas abound in CHI and when you have one, people are eager to discover. CLE is much more enterprise-conservative in its thinking which is ironic being the visionary hometown that it is. If I could wish one thing for Tribe-town, it would be to dream and yes, tear down our lakefront airport like Chicago did with Meigs. Enjoy the great culture of CHI-town and come back to the community!

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