Eight Years in the Second City

Wow, Chicago, 8 years. I settled on job searching in Chicago after ruling out several other big cities where I had friends. Those places all felt too far, too big, too stuffy. But Chicago, Chicago felt like I could tackle it. 

I remember the day I moved here from a full-time newspaper editing gig for a two-month PR internship at a nonprofit. I unloaded my suitcases in a friend’s furnished, extra bedroom in Lakeview for a few weeks until I found two random Craigslist roommates (coincidentally in an apartment just blocks away). Looking back now, I can’t believe I was that brave. I had just turned 24 and figured even if the part-time internship didn’t work out, I could find something else to pay my rent. Luckily I didn’t have to, but I did have to get two more part-time jobs to make ends meet, and enough money to explore my new city. Several months in a friend came to visit. After walking him through the steps to buy a pass for the ‘L’ and board he said, “Who would have thought – Jennie Szink showing me how to ride the train in Chicago?”
 
I guess to my friends from Ohio and Michigan, I might not have seemed like a Chicagoan, but I quickly felt like it here. Although at the time, I didn’t imagine the love affair I’d come to have with the public transportation – its tracks were still too close to my bedroom, the train shaking me awake at night! I didn’t know that in eight years, the same college friend who let me crash my first week would take me out for dinner on my 32nd birthday at what would become one of our favorite restaurants in Lincoln Park. Or that one of the two girls I met and moved in with from Craigslist would be in my wedding party, or that I’d be in hers as she married one of my best college friends! I wasn’t even aware Steve existed in this city yet, beating me here from Michigan by one year. 

As you can probably guess, I didn’t really have a plan when I came to Chicago. In fact, it was a miracle I even chose the city. The last length of time I’d spent in here was a year and a half earlier for a miserable Sisters Trip in January. My sister, Emily, and I tried to navigate the L’s pink line to go to a a Bulls game in an arena that felt so far away from the Magnificent Mile, and after returning to the hotel room, I refused to go back out because I couldn’t stand any more cold.

But when you decide to live your life here as a 20 something, and you come in the middle of the summer, you forget about that cold winter trip. (Much as you’ll forget about the polar vortex years later to convince yourself it’s worth staying in this freezing city.) It’s sunny and inviting and full of other young people dying to make friends and stay out until close at the 4 a.m. bars. (Only did that a handful of times, truthfully.)

It’s big enough that everything feels new because you can explore a different neighborhood every weekend. But it’s small enough that you always run the chance of bumping into someone – which I did at one of my first masses in my new neighborhood. “Jennie Szink?” a woman asked as she approached me at church, and I instantly remembered her as one of my best friends from CCD in middle school. Suddenly, she and her two roommates were built-in friends for said 4 a.m. bars in the coming years.

I recently heard a podcast host say “Chicago is a great place for a 20 something,” and it certainly was for me. I was independent and excited by everything, and now the not-so-good times (roommate fights, heartbreaks) are just slightly amusing memories, because they’re the stories you can only have from your 20s. The backdrop of Chicago is what makes the memories complete – having a boy ask you out after you met on the L just stops earlier; riding in a cab on Lake Shore Drive to get from one night out destination to the next; dressing up for “hipster Sundays” as a nod to the evolving Wicker Park; a Big 10 bar package for your 25th birthday party; huddled under a blanket with friends during Movies in the Park because you underestimated the chill from Lake Michigan; the list goes on and on.

Chicago isn’t just for the 20-something, as the last two years have taught me. We’ve all moved out of our shared apartments and many in with our partners, even some with babies now. Friends have homes across the city and suburbs. My bridesmaid and former roommate offered me her finished basement, should I ever need a place to crash. I no longer need to be out at late-night bars to meet someone, because I met Steve and we moved to the West Loop, where the Bulls games really aren’t that far from. 

I do still marvel at how beautiful the city is in the summer. (Hell, even in the winter it’s pretty amazing as a frozen tundra, as long as you don’t have to be outside for long.) After my first internship in Chicago turned into a full time gig, I stayed there a few years, then moved to a communications agency downtown. My commute home is a walk along the river, one of the best Chicago sights, in my opinion. I’ve seen it five times a week for nearly five years, yet at least once a week I stop to take a photo. Maybe the light’s hitting the river differently than usual, more boats are out on the water, or I’m just reminded that I’m truly lucky to get this view day in and day out. 

When I’m home and feeling nostalgic on nights like this, I think about how eight years isn’t really that long. But eight years as a young professional in a big city, those could be some of the biggest changes of your life. Then, I realize it’s past my bedtime, and I go to the room I share with my husband (!) and turn out the light. And I don’t hear the L from our bed at all.  

 

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