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Meet Caroline Macon

Today we’d like to introduce you to Caroline Macon.

So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
I always, always, always wanted to be a writer. And when I was younger, I took myself like, way too seriously. In eighth grade, I told my friend’s mom, “I don’t think I should join theatre in high school because it is not what I want to do with my life.” I wanted to be a writer in the long-term, so I thought I should give up theatre, haha. She assured me it was okay to have hobbies, especially in high school.

So I did acting and was just okay at it. Then, sophomore year, my school hosted an evening of student-written work. I wrote a 10-minute play called Creeps and suddenly like, I was a playwright. It totally clicked. I expanded that play into a one-act and produced it at a community theatre with my friends. I’ve written plays ever since.

My senior year of college, I met Heidi Stillman. She is the Artistic Director of Lookingglass and she directed my play, The Women Eat Chocolate. When we met it was kind of crazy because we were like kindred spirits. Since then, we’ve done all kinds of stuff together–we wrote a children’s play for Chicago Children’s Theatre, work in the new play program at Lookingglass, and I think she likes having my input on all her stuff. It’s been an honor to have a mentor who is also a friend.

Besides Lookingglass, I’m an inaugural Tutterow Fellow at Chicago Dramatists. I’ve written two plays in my time there, and the journey has been charming and informative and stressful all at once. I’m also a 5-year member of Poems While You Wait–we travel to different events around the city and write typewritten, commissioned poetry on command.

Besides just the plays and the poems, I write other stuff. It’s so much stuff that I don’t even know how to categorize myself. I’ve become like, a journalist, essayist, fiction-writer, reviewer. Who knows? The bottom line is that literary citizenship is hugely important to me, and I try to serve the community by contributing to work that isn’t just mine. I like to review other people, I like to help companies create content for their sites, I like to contribute to the news and feminism and our current political climate. It’s a critical time to use talent to advocate for something. Because if not, then like, what are we doing?

We’re always bombarded by how great it is to pursue your passion, etc. – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
Yes and no. There are many good writers in the world, and sometimes opportunities go to people who are in the right place at the right time. That said, I think inspiration is a bit of a lofty idea, i.e. it’s maybe a hoax (?) and that writers who work hard maybe won’t get writer’s block (?).

There are still trials. I’ve struggled financially for a big chunk of life. My father works in food and hospitality, and in the 2008 crash, he lost a job he had for 25 years. In the last decade, there has been a lot more catastrophe–many jobs, many cities, and lots of stress. The service industry really shifted. Now, a lot of management is handled by young people who are waiting for the next big gig. But for some people like, it is the big gig. And they have nowhere to go.

For college, my dream school was The Theatre School at DePaul, and I was rejected! They put me on the waitlist, which was horrible. I lay in bed with my mom and wept, asking, “Is it okay to keep praying for DePaul even though they said no?” Even knowing very little about Chicago, I knew it was where I wanted to be.

At the last second, I got accepted, with a scholarship, and plenty of support from my family and mentors. Because of the waitlist situation, I felt like I had to try extra super hard to prove myself. So I did. I worked a zillion jobs, applied for a zillion grants, and managed to earn a double major and graduate with very little debt.

Then when I had a baby–surprise!–babies are expensive. Most weeks, after the cost of childcare, it costs me $50-$100/week to go to work. Childcare is no joke. Without my supplementary freelance work, I don’t know how I’d even afford groceries. That said, it’s better to have income than to not. And also like, working feeds my soul. I don’t want to not work. And besides my family, writing is the most important thing to me.

What are your currently work on, what’s your focus, what are you most proud of, etc.
I am a freelance writer. My interests are far and wide, but I have a special heart for literature written by and for women, stories about teenagers written for adults, and stories written in a genre that is hard to define. I like poetry and essay collections. I like the newspaper. I like helping people with resumes and websites.

Right now, I’m working on a piece for American Theatre about the work-life balance for parent artists. I’ve interviewed many inspiring folks for that, including the founder of the PAAL, the Parent Artist Advocacy League.

My first publication was a fiction story in PANK Magazine in 2015. The magazine has since been sold, but I’ll never forget the day I got an email from Roxane Gay, who was a founder. She said she loved my piece and wanted to publish it. I was, and am, a big fan of hers so it just rocked me. After that, it was a flurry of activity. My story was mentioned in a few blogs, so my connections expanded from that.

The biggest thing I’ve learned in my young life (haha who am I?) is that one opportunity leads to another. When I get one, it’s like an avalanche, and then a month or two will go by with nothing. Every second of every day is an email hustle. If one thing goes to the wayside, everything does.

So, what’s next? Any big plans?
I want to keep at it, but be kinder to myself. I’ve dealt with depression, and when I got pregnant, the depression was exacerbated. It was unexpected, so I felt embarrassed to even tell people. In retrospect, that’s silly. Because I am good at being a mom and it makes me happy. It’s not for everyone, and it shouldn’t be expected of anyone. But for me, it’s rounded out the person I am.

A lot of people struggle with a loss after they give birth. Like, feeling as though they’ve lost themselves. I’ve had some of that, but my mom always says, “The baby moved in with you, and not the other way around.” That helps me remember I’m still me, and I’m not going to be me. Augie is a year old now, and I want to hit the ground running with next big things.

Contact Info:

Image Credit:
Photos by Charles Osgood, Michael Brosilow, Caroline Macon

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