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Who made you see Chicago differently in 2022?

We asked both transplants and lifelong Chicagoans for our January 2023 issue. Here's what they said.

At Gertie, 2023 is all about perspective shifts. I’ve noticed that over time, the stories we tell ourselves about ourselves get reinforced by routine, and often, it takes someone or something to show us the mundane with fresh eyes.

Over the years, my own personal geography of Chicago has changed. If I still saw the city the way I did in grade school, I never would have moved back. But because I had the opportunity to produce theater with Steppenwolf and Hebru Brantley while living in New York and Los Angeles, I got to see the city through a new lens (from the outside) and meet communities of people who allowed me to envision a different experience of Chicago as an adult. My friend Alexa Rice, a social entrepreneur with a passion for climate justice, also moved back during the pandemic. “I’ve been experiencing Chicago like someone who’s never lived here before,” she told me.

At the (A)Part launch party last year — hosted by Symone Wright and Hailey Losselyong — I spoke with a woman who expressed a desire to move away for a change in scenery. She described a feeling that's familiar to a lot of single millennials: “All my friends are getting married or starting families, and I feel like I don’t know what to do, or who to hang out with anymore.”

I asked her: "Instead of moving away, what if you just changed your experience here?” Because our city has so many layers, we're constantly seeing it with fresh eyes thanks to the people and organizations around us. Sometimes, it takes an introduction to a new neighborhood or community to see yourself differently in the same place.

For our first newsletter of the year, we asked both transplants and lifelong Chicagoans: Do you remember a time or person who introduced you to a whole new layer of Chicago? Did you get involved with a community or ‘scene’ that made you see Chicago differently?

Here’s what they said.

Emily Brown, who works in venture capital, told me the Chicago marathon pushed her to explore new neighborhoods. “Over the course of 26.2 miles, I ran through almost 30 neighborhoods and experienced a different, beautiful side of Chicago at each turn.”

Product manager Symone Snowden-Wright was invited to a neighbor's holiday party this past December. Even though it was 35 steps from her front door, she met members of the 25th Ward IPO (Independent Political Organization). “The vibrant energy of the group members coupled with their passion for the 25th Ward was infectious,” Symone said. In a plot twist, she is now the newest member of the organization. “Their passionate chatter about the politics and changes of the neighborhood was something that deeply resonated with me,” she said.

At the end of 1996, Jackie Kaplan Perkins began work as the finance director for congresswoman Jan Schakowsky. “At the time, I had only been out to myself and family and friends for a couple of years,” she said. Unbeknownst to Jackie, her boss was one of the few straight elected officials in Illinois who advocated for the LGBT community. “My connection to Jan gave me instant access to a community of which I was a member but did not feel a part,” Jackie said. “Soon, I was attending queer women-identified community events, from the Backlot Bash behind Ann Sathers on Belmont, to Lesbian Community Cancer Center at Southshore Cultural Center.” With all of this engagement came new understandings: of being “in the life,” of the difference between being a “soft butch” and a “tomboy,” of embodying and embracing the word “dyke,” and of the pure joy in hugging someone and wishing them “a good pride.”

While growing up, the Wicker Park and Humboldt Park art communities opened Armani Howard’s eyes to the possibilities of having an art career here. “There was an energy that covered these neighborhoods of art, music, fashion, etc. that I don’t think I ever had ever interacted with,” Armani said. “It definitely forced me to push myself to see more of the city."

For Brenda Jacobsen, the investor Britt Whitfield has been a great connector.  “Britt never misses a moment to celebrate and has built a portfolio of businesses to do just that,” Brenda said. “Britt’s business, Revel, restored 2400 S Michigan and seeing this landmark brought back to life shows me as much about Chicago’s past as it does about its future.” Together, the friends have explored places like Apolonia and Reggie’s Chicago “along with some great residential buildings in the area,” Brenda said. Plus, the parties at Revel Motor Row “certainly bring a lot of energy and new visitors to the neighborhood.”

SoHo House Cities Without Houses manager Erica Jackson was born on the east side of Chicago, so downtown and the northside never felt like home. After time on the East Coast, she moved back a year ago with a transplant’s fascination. “Being in the hospitality space, I've been allowed to meet wonderful people who have become part of my ecosystem and have exposed me to areas within the city that I would not have otherwise occupied,” she said. “Abby, you've been one of those people for me.” Our adventures together, Erica said, have offered "a new clean lens into a city that I saw a different, colder side to while growing up. I'm like a tourist in my own city and it's quite refreshing.”

A few years ago, a long-time Chicagoan introduced Aretae Wyler to an organization called Facing History. “Although Facing History is a national organization, it has a very active Chicago office that provides curricula and training to local schools and teachers,” Aretae explained. “Facing History’s goal is to build empathy, tolerance, civic responsibility by connecting the lessons of history tangibly to today. Facing History has created Chicago-specific curricula around Chicago’s Red Summer of 1919 and the Great Migration, which I find incredibly helpful to understand many challenges we face today as a city, including neighborhood segregation.” Although Aretae is not a student or an educator, Facing History has helped her understand some of the historical subtext of the city. “I’m so glad the organization is making sure those lessons are passed to younger generations of Chicagoans!”

In all of these stories, there is a common denominator: most of our friends’ discoveries and perspective changes and narrative shifts happened because people invited them in.

That’s part of what we hope to do with our content and events over the coming months. Gertie is the discovery and engagement platform that puts you in the center of Chicago’s arts and culture scene: If you’re not already, we want you to be part of cultural moments and communities who make them.

Think about your own experience of Chicago. Who has helped you see the city through new eyes? What did they show you? Why did you find it meaningful? And if you feel stuck in a rut right now, or like you need to change your personal geography, ask your people this question: What is your favorite place in the city? Will you bring me there?

Happy new year!

Xx Abby