Content & Cocktails: An Interview with Cosmopolitan's Ashley Oerman

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How She Got There

An Interview with Ashley Oerman by Emma Garza

Let’s be real—we’ve all watched those iconic movies like 13 Going on 30 and The Devil Wears Prada and imagined what it would be like to work for a magazine in New York.

After interviewing Ashley Oerman, deputy lifestyle director at Cosmopolitan Magazine, it’s become more apparent than ever the hard work, years of experience and commitment to creative vision that goes into producing content for the iconic fashion and lifestyle publication we know as Cosmo (which they never show in the movies).

Having written for Women’s Health, College Fashionista, and various media sites and newspapers, Ashley has earned her fair share of experience in the industry. As deputy lifestyle director, Ashley curates the lifestyle section of the magazine to stay fresh and relevant, covering everything from fitness and health to cocktails and entertainment.

In this interview, Ashley gave some key advice for writing a quality article, tips on breaking into the magazine industry, and the important lessons she’s learned along the way.

Did you always want to work in content creation? If not, what was it that led you to knowing what you wanted to do?

Yes! I was always reading magazines like Allure, Seventeen, and Cosmo, and I knew writing was something I was pretty good at. But it took me a while to realize that a job in magazines/digital media was something that was accessible to me. By my senior year of college, I was pretty set on finding a magazine gig in Chicago (I'm from Iowa) or even New York. 

What was the most valuable lesson you learned from your least favorite job?

My first job was an editorial assistant at XO Group, which used to own The Knot magazine as well as The Nest and The Blush websites. It was back in 2012 when media companies were starting to discover that posting stories to social media (mostly Facebook) brought in so much traffic. Other than that, there really weren't any guidelines as to what kind of content I should be producing, so I just pitched whatever felt like a fit for our brand. 

I didn't have a lot of direction in this position, which helped me realize that data (what your readers are clicking on and how they're getting to your brand) is so important for content strategy and goal setting. Another part of my job was to do some backend CMS work to make sure that our digital stories could be re-published by larger news outlets. Even though that CMS task was challenging, I learned that editors need to be able to troubleshoot coding issues in addition to being great writers and editors. Lastly, I was laid off from that job after 8 months when they shut down the site. I learned that it's important to have savings to fall back on because the industry can be rocky. 

The road to becoming a Cosmopolitan editor seems like a long one—what was your first big break in your journalism career?

I feel like there were so many! First, writing for my college newspaper taught me a lot. Second, my internship at Cosmo helped me get my foot in the door at publications that would normally be skeptical of applicants who don’t already live in New York City.

Finally, even though I'd been writing and editing at sites like The Blush and Parents, it wasn't until I started at Women's Health as a digital editor that I really got my writing chops. I learned so much about style, reporting, writing, and interviewing in that job, and it was the first time I wrote longer feature stories. 

What does a typical workday morning look like for you?

No matter where I am, whether that be at home or in the office, I start the day by checking Slack and email on my phone. When I get into the office (or my kitchen office) I look at my digital calendar to see what stories I need to edit to go live that day. Then, I start chipping away at those (if the drafts are ready for me), or I dig into my print queue. We try to work on 3 issues at time, so I might be editing a first draft for July while assigning a story for August, and prepping my pitches for September—all at the same time. In between all of that, I'll respond to press emails, assign digital stories, and discuss e-comm strategy with our shopping editor. And, of course, random things from the sales team (like a pitch they're working on for a brand) or questions from the art and photo team about photoshoots pop up all the time. 

What is the most rewarding part about your job as deputy lifestyle director?

I feel responsible for providing our reader with the most accurate, helpful information possible—especially when it comes to reproductive and mental health. I think of her like a little sister.

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“Don’t be afraid to kill your darlings.”

Can you tell us one rule of thumb for writing a good magazine article?

Don't be afraid to kill your darlings. Sometimes you write a really witty line that you get attached to even though it doesn't quite work in the piece. To be a good editor or writer, you have to be willing to cut that for the good of the entire story. Leave your ego at the door. 

What is something you wish you had learned before pursuing a job in the magazine industry?

Always try to negotiate your salary. Maybe not at your first job, but in every job after that. Do your research so that you know your value and ask for more than the company offers you. They might not budge, but if they do, you'll save yourself from losing out on thousands of dollars down the line (there's a reason why companies ask for your current salary). You have to look out for yourself. 

What is some sage advice you would give to anyone who is interested in working for a magazine?

Definitely the above. But also, if you're pursuing a job in media, you have to study the voice and style of the publication you're applying to. Your cover letter should read as if it came straight from the magazine or website. Do not underestimate the power of a cover letter. Oh, and one more thing: Your edit test is your ticket to your dream job. Always go above and beyond by doing your homework (reading back issues and their most recent stories), and giving the editor more than what they asked for. For example, if they ask for 3 story ideas, give them 6. If they ask for a hed and dek for each pitch, give them 4. If you want that job, this is how you show it.

Where are you most excited to go once quarantine is over?

Day drinking in SoHo and eating cheap sushi from the Hearst cafeteria (lame but also my favorite). 

Special thanks to Ashley Oerman for this insightful and inspiring interview. For the latest on lifestyle, check out some of Ashley’s articles here.