20Something: Jack

“Go down that road.”

I was prepared to open this piece by describing my first time meeting Jack, which, to my knowledge, coincided with our interview. But when I tell him how nice it is to finally meet him, he laughs kindly. “We’ve actually met before,” he tells me. So we’re off to a great start.

“Oh god,” I say, “was it on The Boat?”

He laughs again, and nods. “It was on The Boat.”

On a warm June night last year, a few of my girlfriends and I joined a group of boisterous frat boys for a sunset cruise along the Chicago River to celebrate their graduation. We laughed and danced and drank as the sun sank behind the skyscrapers and the sky faded from blue to pink to black. When we docked, we stumbled, laughing, off of the boat and through the streets of downtown Chicago in search of a place to carry on our fun. It was during our hunt that Jack and I met. 

It was only a passing introduction amidst the drunken chaos of our group, most of us at the point in our nights when memories begin to falter and we realize a glass of water might be a good idea. 

He followed me on Instagram a few weeks later, and over the past year we’ve slowly developed an online friendship, indicative of our generation, that has never reached beyond story replies and compliments to each other's style. He’s also a writer, and I’ve had a sneaking suspicion for a while now that we’d get along well if our friendship ever left the confines of a phone screen. This interview confirmed my suspicions.

Jack has a gentle energy about him, reflected not only in his thoughtful responses to my questions, but in his posture and clothing, too. He’s wearing vintage jeans in a faded dark wash and a white graphic tee. A striped button down (unbuttoned) sits comfortably on his shoulders. He’s completed the look with black penny loafers (pennies included). He doesn’t use his hands much when he talks. 

We sit down at a coffee shop, I with my latte and he with his matcha. He tells me he recently quit coffee. The horror. “I was an addict,” he jokes. He jiggles a penny loafered-foot. I explain that I’ve been excited to interview him because he’s the first person to be a part of this series who I don’t know very well, so it’s only natural that we begin by getting to know each other. I ask him to give me his elevator pitch.

He studied journalism at DePaul and now works for Chicago Magazine as a fact checker, sprinkling in a piece of writing here and there. He describes the articles he writes for the magazine as “subtle editorial,” but clarifies that he isn’t a staff writer yet. His goal for next year is to begin freelancing - he’s found that he prefers the freedom of it to being told what to do. 

I ask him if there is a particular genre of writing he wants to focus on. I’ve read his blog, and it’s filled with pieces that are short, yet deeply observational and filled with details that paint a vivid scene. Reading an entry makes you feel as though you’re experiencing the moment with him, having the same passing thought in the park or listening to Latin music fill the backdrop of a beach sunset. I’m curious if his professional writing mimics his personal pieces. 

“I’ve always been interested in human interest stories,” he says. That checks out. “I’ve always been fascinated by people. And then, sort of the underlying theme of that is fashion and personal style. And that goes beyond clothes for me. It goes into the way somebody walks, you know, communicates. So it all kind of ties back to human interest.” He feels that the next step for him, professionally speaking, is covering fashion in some capacity. “I’ve always said my dream job is GQ, being on staff there. Like, if I got a job at GQ I wouldn’t write for anybody else. Endgame.”

In the interim between the present and his dream, he’s also trying his hand at poetry. Pushing a tight brown curl out of his eyes, he walks me through his inspiration: Patti Smith’s Just Kids (“I’m reading that right now!” I chime), Joan Didion, Kathleen Rooney, Grace Dougherty, and a lightbulb moment he had at Pitchfork Music Festival this past summer.

“I saw this artist, Dry Cleaning… I don’t know the singer’s name, but I was absolutely just mesmerized by her presence and the way she spoke.” He describes her lyricism as being akin to the words you mumble when you wake from a deep sleep.  He says it was this revelation that spurred him toward poetry. He started working on a zine this summer, and hopes to turn it into a series based on seasons. 

My head snaps up from the notes I’m taking. It’s like he reached inside my mind and pulled out an idea that was just beyond the forefront of it.  “That’s crazy,” I interrupt. I tell him about a recent idea I had, one for a zine series based on seasons. This is the first of several synchronous thoughts we’ll have throughout the interview. Each time, it makes me marvel at how connected human beings can be, even when we don’t realize it.  

Getting us back on track, I ask him about his journalism degree. “Did you major in it all four years?” Yes. “Did you pick it right off the bat?” Yes. “And you’ve never wavered in that?”

“Definitely wavered. Always going back and forth. Though I’d say about halfway through college I knew it was for me.”

As he tells me the story of how he fell into writing, I realize it’s almost identical to mine: he wrote imaginative stories growing up, and once he hit high school, his teachers were quick to compliment his skills. He appreciated the praise and accepted writing as a strong suit, but could never really work out whether his affinity for it was born out of his own enjoyment, or from the validation he received from his teachers. “It was sort of this back and forth between agency and believing it, but also being, like, ‘Oh, I’m doing this for somebody else,’” he explains.

Ultimately, it was a creative writing class he took during his junior year in college that pushed him beyond his comfort zone and cemented his passion for writing as something he could claim as his own. Since then, he’s been working on finding his identity as a writer and falling in love with the art form. 

I ask him if he ever grapples with the pressure of turning his passion into a career. It’s something I struggled with immensely in my time as a dancer, and has made me shy away from treating my other passions as anything more substantial than hobbies. He admits that the days spent reading, writing, and fact checking can be draining and often leave him with little motivation to work on his own portfolio. “I’ll say this though…. Writing, for me, as much as it can feel like a job… it has never been something I feel obligated to do.” He says writing feels like a necessary bodily function for him. A means to survive. “Writing is just something I have to do.”

I wouldn’t be surprised if strangers often pegged Jack as a writer upon first glance. There’s something about his demeanor, or perhaps it’s his style, that exudes “literary”. Jack, like myself, roots a large part of his identity in his personal style, ever-changing as it may be. It was one of the things I was most excited to ask him about.

When he begins to tell me about his journey with fashion and style, it takes me completely by surprise. He’s always been fascinated by style and the way that he presents himself, so much so that he would bite his sleeves as a child, trying to emulate the frayed look that he liked so much. When he was around the age of 10, his parents took him to a Blackhawks game. “While I was watching the game, the thing that I was most interested in was how the players looked with the shoulderpads and the skates.”

“Like the silhouette of them?” I ask.

“Everything,” he says. “Everything about it. What attracted me to the game was not the game so much itself as it was how they looked in the uniforms. So then I started playing hockey.” 

Here’s where it gets interesting: he explains that style is a huge part of hockey, not just in players’ clothing off the ice, but in the way they don their gear, or wrap their sticks, or pair their helmet with their gloves. While he eventually left hockey behind, he took the practice of dressing intentionally with him. He feels as if he’s filled some of the void that hockey left with fashion. Uh, that feels familiar. 

Now, he finds most of his style inspiration through well-dressed women on Instagram. “I’ll go to these pages, and see what kind of fits they’re rocking with, and I’ll be like, ‘I’m gonna do something along the lines of that.’” 

I ask him what his perfect style recipe would be.

Jack McGann’s Perfect Outfit

• 1 white t-shirt (can substitute with black)

• 1 pair of vintage Levi’s

• 1 blazer

• 1 pair of black or burgundy loafers (pennies in)

I’m jealous that he’s been able to find a good pair of vintage denim. It’s the one part of my closet that I feel is still lacking. I make a mental note to try Depop again.

We’ve been talking for almost an hour now, and the conversation has yet to fizzle in the way that first meetings sometimes do. 

I want to dig a bit deeper at this point, so I ask him to tell me about the best and worst years of his 20s.

“Can I start with the worst?” he asks.

“Of course,” I say.

As he begins to speak I watch his demeanor change, so slightly that I almost think I imagined it. He tells me that his 22nd year was one of unrequited love and eventual heartbreak. He was living alone at the time, caught in the throes of isolation that so many of us in our early 20s are familiar with. He had written a story in his mind, one that told of a relationship far sunnier than its reality.

“It really changed my perspective on giving myself to somebody… I feel like I unveiled, sort of, the deepest things about myself. I was as raw as I could possibly be. And then for that not to be reciprocated….  There was a lot of negative self-talk.”

As he finishes describing his experience, he seems more self-assured. “It was also a period of deep self-exploration. I went vegan… I was doing pushups… I had demons,” he laughs. “So that’s probably the worst year. 22.”

And the best year?

“24. Where I’m at right now. This has been the best year of my life.”

He sits in silence for a moment as he tries to articulate what it is that’s made this year so fulfilling. “Sometimes you get a sense that something is different in you,” he explains. “You get a sense of, ‘Oh, this wasn’t here before…’ I departed from a version of me that was fixed on the past.”

He leaves me with something his dad often says to him: “Go down that road.”

“That’s sort of my quote of 24… Suppose it goes wrong. Suppose I entirely misjudge a situation, whatever it is. I went down that road. I can sleep well at night knowing that I put myself out there. I tried. I learned something.” 

If you want to read Jack’s musings, check out his blog. I highly recommend it.