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  • Michael Feeney

In Conversation with Writer's Digest's CASSIE LIPP

Writer’s Digest Managing Editor Cassie Lipp has graciously joined us in conversation about her experiences with Writer’s Digest, her writing, and more.

Writer’s Digest is such a wonderful resource for both seasoned and aspiring writers. Give us a brief overview of your journey with WD and how you ascended to the position of Managing Editor.

It’s kind of a funny story. I graduated from college with a degree in English and journalism. Then I spent the next two years freelance writing and teaching creative writing while applying for jobs. I didn’t expect it to take nearly that long to find full-time work, but I’m glad that I continued to build my portfolio rather than taking whatever job I could get to pay the bills because I worked on some pretty amazing projects during that time. I was hired by the photographer Mike Spitz to write the text of Queen City Records, a coffee table book about the record stores of Cincinnati and Northern Kentucky. Mike isn’t a writer himself, so he needed a writer local to Cincinnati to go to all the stores and interview the owners. He self-published that book at the end of 2017. I also began my own literary zine with a friend from college because I knew I wanted to work in publishing but didn’t exactly know how to break into that industry living in a town with zero publishing jobs.

Then one day I saw the job opening for Associate Managing Editor of Writer’s Digest on LinkedIn. I was already familiar with the magazine because one of my journalism professors pointed us toward WD as a great resource on all things writing. My habit of checking the job listings daily because I had nothing better to do (okay, sometimes multiple times a day) worked in my favor because I was the first person to apply for the job! The work I did as the author and publicist of Queen City Records and the issues of the zine I made impressed the editors and publisher of WD enough to offer me the job. Then in March of 2019—five months after I started—FW Media, the parent company of WD, filed for Chapter 11 bankruptcy. So for the next five months after that, I got a crash course in everything they don’t teach you in journalism school: learning to take on (a lot) more responsibilities when other staff are leaving and not being replaced; how to pitch new ideas in times of uncertainty; how to operate a publication under dwindling resources; etc. All this translated to proving my worth as a valuable asset to WD once it was purchased in an auction by our current owner Active Interest Media, so I was promoted to Managing Editor.

What are some of your responsibilities as Managing Editor?

As Managing Editor, I am the main person in charge of the print publication. So I give the editor-in-chief my input in which articles to commission, then do everything from giving articles a first-pass edit to writing the headlines, copy editing, creating coverlines, and proofreading the issue. I own a few columns, so I select and interview authors for Breaking In; create the puzzles for Potpourri for the Pen; and read all the Your Story writing contest entries to pick the winner. For the past few issues I’ve also written our big annual features, like the 101 Best Websites for Writers feature and the literary agent roundup. I’ve also been lucky enough to interview some authors for feature well interviews, including Ross Gay and Samantha Irby.

Let’s talk about your personal writing journey, your poetry, and Queen City Records. What have been some highlights of your writing career and what has been some main inspiration behind your work?

I began writing poetry in college because the fiction writing workshop was full. But I ended up loving poetry, so I took more poetry classes whenever possible and continued writing poems until about a year ago. I hope to pick poetry writing up again and publish those poems in a chapbook, but for now I’ve been focused on writing creative nonfiction with a humorous tone. I picked up humor writing because when FW filed for bankruptcy, I was a mix of frustrated and confused about what I wanted to do with my life if my job with WD came to an end. Working for a bankrupt company can be pretty stressful. So I turned to reading books by Samantha Irby and David Sedaris when I got home to get through that rough patch with laughter. They are both so funny, and they also made me want to write like them. The other WD staff kept telling me I was funny, so I thought maybe writing humor was where my life was supposed to go in that moment. I followed that lead and I’m still there now, writing in any spare moment I get, mostly on the weekends. I keep a little notebook where I jot down any ideas I get that would be funny to write about so I don’t forget them. Anything that’s happened in my life is fair game. Most of my essays deal with the weird things I did as a kid because I didn’t have any friends, plus a few things from my young adulthood. I’m only 25 so there isn’t much else to write about…yet. Editing WD has been a huge inspiration. I can’t help but think about how I’m going to apply each piece of writing advice to my own work as I’m creating the magazine. I just feel like a wimp if I come home and I’m not working on my next project after conversing with so many great writers all day. The amount of writing I’ve been doing since taking over as editor has increased tenfold.

You are especially passionate about independent publishing and small press. Recently, you were responsible for Writer’s Digest’s April Issue highlighting the best of indie publishing. What fuels your efforts and what makes you so passionate about advocating for small presses?

There’s a lot of reasons why I love independent presses. I’m an avid reader of poetry—there are so many poets whose words have moved me, changed the way I see the world, and their books would not have been published without small presses. With the exception of a very small number of imprints, the Big 5 and Amazon publishers don’t really put out poetry collections. So there wouldn’t be many poetry books traditionally published today without the existence of small presses.

That’s just one example of the type of books that don’t get published by larger publishers. Many publishing companies acquire titles based on what they think will sell well and aren’t very willing to take big risks. But isn’t taking risks on books that are experimental/ unique/ telling an important story how the literary landscape evolves? There’s just so many groundbreaking books being published by independent presses today that these small publishers are too loud to ignore.

This is not to say that large publishers aren’t putting out great books. They’re just not the only ones publishing books worthy of our attention. If you are reading as widely as you can, which is something that all writers should do, it’s not possible to get an accurate grasp on all the types of books being published today without looking at small presses too.

When choosing authors to feature in the Breaking In column, I make sure to feature at least one small press author each issue because I want to make sure that releases outside of the Big 5 get the attention they deserve. Many authors I’ve featured in the column have had success selling their manuscript to a small publisher without an agent. I think that’s important for our readers to know—that it is still possible to find a home for your book even if you are having trouble finding an agent.

What do you see for the future of independent publishing?

I think the (at the time I’m typing this) 8,500+ follows on the PublishrsWeakly Twitter account shows that there are a lot of people—authors, editors, agents, publicists, booksellers, etc.—who are unsatisfied with the current state of the publishing industry. Yes, there are many great books being published today, and there has been a lot of progress in including more diverse voices in the books that get published. But there are a lot of issues hindering the progress that still needs to happen. Some issues I see are the fact that the majority of the industry is located in the most expensive city in the U.S., and most publishing jobs pay salaries so low that it’s pretty common for publishing professionals to need to work a second job or rely on the support of a partner or family member to survive. I don’t think this system is sustainable, nor conducive to getting the stories we desperately need but aren’t yet published out there. The current COVID-19 pandemic is illuminating some of these issues and will hopefully incite some change for the future.

While independent publishers aren’t immune to these problems, many are able to side-step some of these problems that plague bigger publishers. For example, nonprofit presses aren’t beholden to shareholders, and there’s small presses located around the nation. Many are making their mark, with titles topping bestseller lists and winning literary awards. Readers are taking notice and supporting these releases.

As time goes on, I can see independent publishing taking an even bigger slice of readers’ attention. It won’t be just Graywolf, Coffee House, and Milkweed one the forefront of readers’ and booksellers’ minds when they think of independent publishing; the hundreds of other small presses out there should also rise in popularity. I also think an increasing number of authors will consider independent publishing when it’s time to sell their manuscript.

In your bio, it states that you are currently working on your debut essay collection. That’s very exciting. Can you divulge any information regarding the focus and your goals for the project?

It’s hard to describe because creative nonfiction deals so much with anything that happens in your real life. The best way I can describe it now is that the essay collection will cover all of the bizarre things that I’ve done or have happened to me in my life, plus anything else that occurs from the time that I’m typing this to the time that I sell the book. So far I’ve written about 15,000 words that could go into it, including some pieces about a phase I went through when I was addicted to the Magic Bullet infomercial (my favorite); how I found myself forming a coven at age eight; the one frat party I went to in college just so I could steal a trophy off the wall; and other ridiculous things I’m too embarrassed to casually talk about. But revealing them all in creative nonfiction is so freeing. I want to traditionally publish the book, so I plan to shop it around to agents when I’ve got more material written. In the meantime, I’m pitching the pieces I’ve written so far to literary journals and websites to build an author platform.

We look forward to more resources and developments from you and the rest of the staff at WD! What are your goals for the near future as managing editor? What other topics do you look forward to focusing on?

I’d really love to expand WD’s offering of digital content. There’s already a lot offered in terms of online classes, virtual conferences, and tutorials, but we don’t have a huge presence on YouTube. I see a lot of well-known publications producing some really great video series on YouTube, so I’d love to be able to do the same for WD. My boyfriend runs a channel of gaming list videos that has amassed 500,000 subscribers in two years. I assist him in producing those videos, so I’ve seen how many people you can reach if you know a little something about YouTube’s algorithm. With everyone being stuck in their homes, the demand for digital offerings is only going to grow.

And as WD’s youngest staff member, I’m always trying to expand our audience in the age bracket I reside in, whether that’s putting a fresh spin on our content to address certain topics they’re interested in, finding new ways to reach our audience, featuring the authors they’re reading in our magazine and other offerings, etc.


Cassandra Lipp worked as a freelance writer for local publications and wrote the nonfiction book Queen City Records, which tells the history of Cincinnati record stores, before becoming Managing Editor of Writer's Digest in 2018.

Driven by a passion for helping other writers improve their craft, she also leads writing workshops and works as a freelance book editor and consultant. Her specialties include creative nonfiction, memoir, poetry, humor, and narrative nonfiction.

Cassandra enjoys penning poetry, humor, and personal essays in any spare moment she gets. Her work has appeared in Points in Case, Ohio's Best Emerging Poets, and elsewhere. In addition to writing, she has been a stage manager and performer with Improv Cincinnati.

She is currently taking on freelance book editing projects. She can be reached at

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