Interview: Megan Weinerman, Copywriter & Author

This week we chatted with Megan Weinerman, a freelance copywriter, author, and artist based out of Chicago. In the latest installment of our interview series, Megan discusses how she got into writing, her intuitive artistic style, and the Windy City’s growing startup community.

Twenty Two: Let’s start with the basics. Can you tell us a bit about yourself?

Megan: What would you like to know? Where I was born? NYC. Where I was raised? City of Chicago. What do I do? Freelance writer in advertising.

Twenty Two: Have you always been interested in writing?

Megan: No, I fell into it. It was like an accident. I was working in TV production in NYC for VH1 and I started writing in a journal, doing improv, and studying stand-up. Shit like that.

Then a friend of mine was going through a bad breakup with her boyfriend. She was living in LA and I started sending her these funny/cute cards that I had written. She loved them. She’d always wanted to start her own company, so one day she called me up and said, “Let’s start a company together. You write funny stuff, I’ll market the crap out of it.” It went something like that. The gist of the story is on my website,, under “She Work.” But that’s how it started. Then after being with the company for three years, I moved home to Chicago to take care of my parents. I put everything together that I’d done with the company and put it in a portfolio and hustled ad agencies for writing work and ta-da! Here I am almost ten years later.

I’ve written humor books, greeting cards, advertising, screwed around with a TV pilot script, and screwed around with a kid’s book. I just got off a six-month gig writing for Claire’s, the tween/teen accessories brand. That was fun! I rewrote the brand “voice,” as we call it in the “biz.” I rewrote their voice to sound more like a 13-year-old on Twitter meets Dr. Seuss meets a rapper meets a fashionista. It was a blast. Then the client and the agency I was working with/for decided to change direction and they no longer needed me. C’est la vie.

Twenty Two: How would you describe your writing style?

Megan: Direct, empowering, oftentimes humorous. I try to us my voice/perspective to help bring connections together. That’s what a good ad writer does: helps show connections, whether to each other, a product or blah, blah, blah… And I try and keep things simple. Simple is best. I was trained in journalism in college, not English. So I’m more interested in being clear and direct than flowery. Make sense?

Twenty Two: Definitely. Does writing humor come naturally for you or did you develop it while doing improv and stand-up?

Megan: Doing improv and stand-up was a test for myself to try and learn new tools. I was always considered “funny.” A lot of ad writers take improv to help hone their writing skills. It helps with the whole “thinking on your feet” thing that you have to do in the ad biz and it helps with the creative process. An improv tenet is “yes, and” which means you have to go with the flow of an idea instead of negate it. You have to let ideas flow first before you kill them. Besides, in advertising your boss and client will happily kill them for you! What I’ve come to realize in my work is that the creative process is more of a positive process than a negative one. Meaning, you have to say “yes” a lot more than “no” to ideas to get anything done. Then you edit, massage, hone, ensure that it fits a strategy. Thus the word “process.” I don’t think creativity comes out of chaos like many people are led to believe.

Twenty Two: Where do you find inspiration for your writing?

Megan: It’s always based on the project at hand, never out of thin air. A lot of times though, when I’m at work, I like to approach things like, “What if this wasn’t a website? What if it was a magazine? What would it look like? How would it be written?” I try and take the thing we have at hand, and see what it would be like if it were another “thing.” There’s an old joke about ad creative: “How many ad creatives does it take to change a light bulb?” And the ad creative interrupts the joke and says, “Does it have to be a light bulb?” When you can look at something from another perspective, that’s usually when inspiration comes. That’s when inspiration usually happens.

Twenty Two: You’ve mentioned that you’ve published a few books and you have a couple on the way. Can you tell us a bit about this?

Megan: The humor books were done when I was with my old company and the children’s book was done while I had some downtime during freelance gigs. It’s not published or anything and now I think I need to rework the drawings. It’s one of those art projects that you pick up and put down as other things in life take a hold of you. I’ll probably try and self-publish it someday. Getting a publisher for anything is hard.

Twenty Two: Speaking of drawings, in addition to being a writer, you’re also an artist. How would you describe your artistic style?

Megan: Definitely intuitive. I call my artwork an “artistic meditation.” I would never market myself as an artist for hire. I can’t say, “You want a picture of a landscape? And you want a lot of the color blue? I can do that for you!” The stuff’s definitely more conceptual. It’s usually not until I’ve done the piece that I know what the piece is about. Right now I’m working a lot with hand cut paper on paper. Cutting the paper into fluid shapes feels meditative to me. Why? Who knows? But I’ve done a series of greeting cards that I’ve sold. And I sometimes do some illustrations, color marker on paper. I was a fine art minor in college. I got all C’s because I had nothing to say. I guess it took all these years to finally say… something.

Twenty Two: Which projects are you most proud of?

Megan: Ah! The customer mailer series I did for the high-end boutique ikram in Chicago. I got to do the customer mailer series twice. Both series are on my website under “She Work,” too. They were fun approaches to how to think about fashion. They were very fun to do and the ideas came to me very quickly. It was just about joy.

Twenty Two: How has living in Chicago influenced your work?

Megan: Well, Chicago is very grounding for me. My friends and family are here. I’ve lived all over California and New York, and never thought I wanted to move back here. But when I did, something felt like “home.”

Twenty Two: When you’re not working, how do you spend your time?

Megan: Oh, that’s easy. I’m learning how to meditate, I work out, I network, hang out with friends, and hang out with my boyfriend all the time. Oh, and I’ve also been writing articles for Technori. They’re dedicated to the startup community in Chicago. They have an online publication and hold a lot of networking events. It’s pretty exciting to see the change in Chicago. Ten years ago, this type of community didn’t exist.

Twenty Two: Are you very involved with the startup community in Chicago?

Megan: Through Technori. I’m not in a startup myself. I meet a lot of people starting their own companies. It’s fun, but I don’t have a “big idea” of my own right now.

Twenty Two: Are there any exciting startups based in Chicago that we should look out for?

Megan: Well, Technori is a startup itself! I’m very proud of the founders Seth [Kravitz] and Val [Chulamorkodt] for all their passion and focus on building Technori into what it’s already become in such a short time. They’ve only been around for a little more than a year, and they’re rapidly expanding. There’s clearly a hunger for the type of networking/educational events that they can offer. They’ve brought on a new editorial staff to expand the content on the site, too.

Twenty Two: What can we expect to see from you in the future?

Megan: Hm. Good question. I’m talking to a couple of people about collaborating on some book ideas. One is about mentorship, the other is about dating. I’m still working with Technori, checking out what writing opportunities there are in the ad biz, and thinking about taking some trips with my boyfriend. And of course, I’m always interested in laughing my ass off, so I try and do that as much as possible.

Twenty Two: Do you have any advice for aspiring copywriters, authors, or artists?

Megan: Do. Don’t think.

A special thanks to Megan for giving us the opportunity to learn more about her work. You can keep up with her by checking out her website, blog, Twitter, and LinkedIn.

Click on the images below to see more from Megan.

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