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The CHI and Me: 7 Lessons from Chicago

I finally get to have a picture with The Bean.

There is a common misconception in life that starting work means you have fewer adventures. This blog serves as proof to just the opposite.

I spent the past 72 hours in Chicago—and work sent me there. I worked a conference where 4,000 inner-city 16-24 year-olds came and interacted with hiring managers from companies like Starbucks and Dominos in an effort to employ the city’s opportunity youth. 400 of them left with jobs that day.

But there is always free time to roam. Here are the seven things I learned working and roaming around the Windy City.

1. Conferences are Fun

Six months ago I wrote papers and attended lectures. Now, I go to places where I get a badge that says “staff” on it. People in suits that manage organizations talk to me with a degree of respect (I wore a company T-Shirt, mind you) and when they ask me what I do, I get to say, “I am working with a startup that will change the education space,” as my opening line. It's a much better conversation starter than, "Oh, I'm a student."

Plus the CEO of Starbucks was 10 feet away from me at one point. It’s like corporate royalty.

Double Plus: I ended up in the background of a local news report. Upper lefthand corner. Success.
2.  Deep Dish Pizza and Hot Dogs Reign Supreme

Both of these things are everywhere. It’s melt-in-your-mouth goodness that you can’t escape. Michigan Avenue? You’ll find it. Navy Pier? You’ll find it in spades. It’s great, but it is overwhelming the sheer quantity of places where you can find this stuff.

I’m not saying it’s not great, but come on. Give me a few veggie wraps. Or at least a McDonalds salad. Balance it out a little.

No fear though, I found a great 西川菜 place in Chinatown to keep things fresh. Thanks for the service, Chairman Mao.

3. Ask for Directions, Find Cool Things

When it comes to work, I plan my traveling well. I know where I am going, what I am printing, who needs to have what, and am prepared for contingencies. When it comes to play, I plan not to plan.

I spent two hours wandering through southern Chicago trying to find Promentory Point. The journey took me through part of the projects, University of Chicago, Hydes Park and finally, after asking for directions five times, Promentory Point.

I’m discovering there is something fun about traveling in this style. Sure, it leads to you lugging your baggage around for two hours (probably could have planned that out better), but it also leads to serendipitous conversations and discoveries.

4. Always Stop to watch the Dancing Koreans

This one is basically a no-brainer decision.

I’m walking through Millennium Park. I hear bagpipes. I’m confused, so I walk toward the sound of bagpipes. But it’s not bagpipes. In fact, I have no clue what I am seeing or hearing. The only thing I can figure out from the crowd and the costumes is that I have stumbled upon a bunch of dancing South Koreans.

I thought they were just a group of sound local performers—turns out they are an internationally recognized and protected cultural performance group that performs in over 500 places every year.

Again: serendipitous discoveries are the best.

5. Do Touristy Things

Local Chicagoans drone to me about how “Navy Pier is where fun goes to die” and other such laments about their tourist-facing attractions. Maybe that’s true if you live next to a pier with a Ferris wheel, but I don’t, so I think I will have my fun down on Navy Pier thank-you-very-much.

I read a lot of blogs that really bludgeon you over the head about how true native culture is better than tourist attractions. I agree. But I’m still going to enjoy the touristy things too.

Was it worth paying $40 for an hour-long architectural river cruise? For me, yes. Was it worth being the oldest kid on the spinning swings ride on Navy Pier?

A thousand times, yes.

6. Meet People from the South Side

Most of the opportunity youth at this conference came from the south side of Chicago. I met guys younger than me with two kids. I met people who had difficulty using a computer. I met people who opened up about their whole life with me. If you want native culture, talk to these people. The lives they live are raw.

The South Side right off the 69th street Red Line exit.

But on the other hand, some of them have humility and genuineness that supersedes the average person. I met a girl who was so excited to receive a job from Starbucks that day—she was just excited to get any job so she could afford to get back into school next year at Columbia College.

I grew up in a middle-class community, so a lot of these interactions and experiences were incredibly novel for me. But you learn by being uncomfortable, and if you want to see the heart and soul of Chicago, you got to hear the voices of people from the south side.

7. Talk to People on Public Transportation

I’ll be a realist here: this isn’t a “do-it-every-time” recommendation. Use discretion, because there are sometimes when it is better if you don’t talk to someone on a train.

That being said: don’t be shut off to conversations.

Two of the most interesting conversations I had in Chicago came from two different people I met on the L Train. The first one is a 24-year-old TFA alumnus who now worked in the education department of the Chicago mayor’s office. The second is a 31-year-old rapper and Chicago resident who has never left the city limits. Two totally different people.

Meet Mark. 31 years spent living, 20 years spent rapping.

The education department worker talked about city issues and impending teacher strikes that would affect the city. The rapper talked about how people from the south side have to fight to really make something out of themselves and escape the cycle. He also passed me along a link to some of his music, including songs such as “Murder Capital.” (And as a side note, Mark was one of the friendliest people I met in Chicago. Don't let the picture fool you.)

You want to get a more dynamic travel experience than the hotel lobby? Talk to people like these.

All in all it was a great first trip to the Windy City. The place has definitely whet my appetite—I’ll be back to explore soon. Thanks for reading!

Bean interior.
Entrance to Chinatown.
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