Interview with Self-Published Author Whitney Cubbison
The author of the hit romcom Will There Be Wine? joins us for a Q&A about self-publishing her first novel
Whitney Cubbison, author of Will There Be Wine?, was a career communications executive for Microsoft before she left and committed to publishing her first book. It was a risky move—romcoms are a crowded category, and self-publishing is famously difficult to navigate. However, she managed to break through the noise and has seen great success from a sales and content perspective. She generously took the time to answer questions about her journey and her answers shed helpful light on the complexities of writing and publishing your own book.
Thank you, Whitney!
First, can you tell us a little bit about your journey to becoming a writer?
Technically, I started young! I was a closet diary-writer from elementary school until I got married. It was my way of processing all my youthful feelings, and although absolutely none of my childhood musings are worth revisiting, it created the habit. I stopped writing in that format, I think, because I was finally happy, and therefore didn’t feel the need to hash through my turbulent feelings.
At the time, I was also working for a technology public relations agency in San Francisco, writing press releases, media pitches, and the like, so writing became a professional habit at that stage. I ultimately spent 16 years at Microsoft working in corporate communications, with writing responsibilities spanning public relations, employee communications, executive speechwriting and social media. I wrote for a living, but fiction it was not.
As I think it through, it’s all rather logical that my “pleasure writing” resumed with this novel, which starts on the day of my main character Austen’s divorce. The key lesson here: marriage is bad for writing! Austen is very much based on me, so I suppose Will There Be Wine? is my diary-outlet 2.0 for processing my feelings, albeit this time via fictional prose. Old habits die hard, it seems!
At what point did you realize you wanted to self-publish vs. going the route of finding an agent?
I pitched a bunch of agents in early 2021 and had initial interest from five, which was very exciting. However, in the end, none of them offered to represent me. That small amount of interest was enough to convince me I had a good premise for the book, but it obviously wasn’t polished enough to sell, so I decided to hire a freelance editor to help improve it.
Working with this editor was so incredibly helpful, so by the time I had processed all her feedback and rewritten huge chunks of the book, I knew it was ready to go. At that stage, I was simply too impatient to re-pitch agents and wait another 3-6 months for their responses, knowing that if I did get one, they’d inevitably want me to change some things before they pitched it to a publishing house, and then if anyone bought it, they’d inevitably want even more changes. The process felt way too long and I’m a bit of a control freak, so I decided to self-publish and control my own destiny.
Who were the people you hired to help you put the book together (i.e. an editor, designer, etc.) and where did you find them? What was it like working with them?
When I completed the first draft, I hired a structural editor who I found by word of mouth. At the time, the book was basically one chapter per guy, and for the meatier stories, there was some flashback and/or flashforward within the chapter. Her main feedback was that I should break out those flashbacks or flashforwards and tell them as full and linear stories, to create reader attachment to the returning characters. The feedback seems obvious now, but at that stage I had absolutely no idea what I was doing, so it provided some great clarity on how to move ahead and improve. I pulled the story apart, added around thirty thousand words, adjusted timeframes and put it back together again. It was then that I pitched agents and got nowhere.
So, I hired a copy editor, naively thinking it just needed a bit of polish and formatting. I found this second editor on Reedsy, which is a fantastic resource for aspiring writers, and she turned out to be an angel from heaven. I discovered this fact after she missed the initial deadline for getting me her feedback. I emailed her to ask where it was, and she told me that she needed a few more days because she “loved my story so much that [she] didn’t want to miss an opportunity to help make it great.” She’d started a partial line edit on the book, which she returned to me a few days later. She had line-edited about a third of the book, at no extra charge, in an act of extreme generosity. It was in processing her feedback that I really understood how to write a novel.
From there, I worked on rewrites between 6 and 12 hours a day, 7 days a week, for two months solid, jumping out of bed every day so excited to keep writing. In my acknowledgments, I thank both of these editors for “taking what I vomited out onto a page and teaching me how to turn it into a novel.” I’m so grateful for their help!
Also on Reedsy, I found my cover designer and a proofreader, completing my team. Working with the cover designer was great fun. I had absolutely no idea what I wanted the cover to look like, and we got to the end product within three iterations from her initial proposal. She was a fantastic collaborator who also did the interior typesetting for the book and formatted the final files for KDP and Ingram Spark, which had slightly different requirements. My proofreader was also a real pro, whose comments further boosted my confidence that the book was ready. So, on January 16, 2023, I self-published on Amazon.
As you were going through the process of writing and editing the book, what was the most surprising challenge you faced and how did you push through it?
Having spent my entire professional life writing as a corporate communicator, I was pretty sure I was a good writer. As it turned out, most of the skills I had spent years honing in my earlier career did not serve me well as a novelist. In tech PR/communications, we’re most often writing for a transaction or a sale. You tell people exactly what they’ll get if they buy your product. As a novelist, you have to write for a feeling. You have to be able to transport your readers into the scene and bring them on an emotional journey with your characters. These writing skillsets are NOT the same.
The difference between them really clicked thanks to the feedback of that second editor. As one small example, one of her game-changing comments/questions was “What is she thinking here? Consider adding internal monologue, in italics.” I’d never even thought about internal monologue as a storytelling tactic. Going back and adding that in throughout the book gave the main character a whole new level of depth, exposing her insides and providing the reader with so much more insight into who she was.
More broadly though, I’d say the big challenge was how to take the real-life experiences (and by “experiences” I mean horrifically hilarious dates) that had inspired me to write in the first place and figure out how to create a narrative arc through all of them. Without that, it would have been just a random string of anecdotes, rather than a cohesive novel. I wanted the book to be smart and thought-provoking, as well as funny, so the girlfriend characters became the glue that stuck it all together. It was through their conversations that the reader sees how Austen’s friends helped her reflect, grow, learn, and propel herself forward toward happiness.
The most annoying challenge was formatting the book from paperback into e-book -- because of hyphens. Hyphens became my nemesis for several weeks. In a paperback format, which is the first in the typesetting process, if a word runs off the end of a line on a page, a hyphen is added to continue that word onto the next line. My designer then copy/pasted that text into a new file to format for e-book so suddenly there were a million unnecessary hyphens that all had to be edited out, one by one. I went cross-eyed so many times over the Christmas holidays, trying to make sure all the bastard, rogue hyphens had been eliminated. I’m pretty sure there should have been an easier way, but alas… that’s how it went.
Once the book was finished, how did you go about navigating the actual “selling” piece? Did you use Amazon ads? Work with influencers?
I joined several Facebook Groups for self-published authors as a starting point and read a ton online about how to get started. My first priority starting in November of last year (two months before publishing) was putting together a team of ARC readers, which I found through Instagram by searching for handles that included the words “book” and “wine.” I figured the title of my book alone would be enough to get those people’s attention. I reached out via DM to roughly 50 people, eventually getting around half of those to say yes to reading and reviewing the book for my launch week.
In December, I had the good fortune to meet you, Amy! Despite my having a background in PR and marketing, the worlds of tech PR/marketing and book PR/marketing are not the same. Certainly, having that background helps, but there were (and still are!) so many things about the book industry that I didn’t/don’t understand, so it’s been helpful to work with someone who knows that industry inside and out. I’ve learned that the book industry is very insular, so a lot of the opportunities come through knowing the right people who can crack open the right doors. Flying solo as an indie author, it’s exceedingly tough to do that at any kind of scale. There are just too many books competing for attention.
When the initial round of ARC reviews came in almost entirely with 4 or 5 star reviews, I decided to really invest in marketing, including setting up a seven city book tour in Europe and the U.S. I was fortunate to have the money to invest and while I was nervous to do it, my very smart friend Heather told me “not to nickel and dime my dream” and just go for it. I ended up selling out of books in all seven stops.
As an online marketing vehicle, Instagram has remained my primary focus because of the highly engaged Bookstagram community and also because I happen to love taking pictures. Most of my book takes place in Paris, so I decided to do a whole visual storytelling journey through the book’s real locations on my page. I’ve also been doing regular monthly “campaigns” with Bookstagrammers, creating themed templates for them to share around Valentine’s Day, Spring Break and now Summer reading. I share those custom templates (made in Canva) along with a free copy of the book and rally a group of reviewers around a particular week to create ongoing visibility for the book. And I keep posting Paris photos, which everybody loves. I’ve also been part of two virtual Bookstagram tours, appeared on several podcasts, done some traditional PR, collaborated with a few relationship/therapist influencers, and hosted a few small giveaways on Instagram and GoodReads.
I know I should be doing more video – both on Instagram and also on TikTok – but the easy subject matter is all the truly horrible dates I’ve been on, and to be honest, I am scared that if I start talking about those in real time via video, I will never get another date and will end up single forever!
I’ve also done Amazon ads but because romance/romcom is such an enormous category for books, I’ve found it very difficult to break through. There are some helpful resources available for indies to try and understand the Amazon algorithm from sites such as Kindlepreneur, but in truth, Amazon is intentionally opaque about how their algorithm works, so unless your book speaks to a very targeted niche, it takes a lot of experimentation and persistence to get those ads working for you. In my experience, advertising against the Amazon category called “divorce fiction” has been the most effective, despite the fact that Austen’s divorce is a background point in the overall story of her looking for her second chance romance. It’s a bit of a mystery!
What has been the most valuable or impactful thing you’ve done to help sell your book?
Write a good book! As for the rest, I can’t point to any one thing that’s moved the needle more dramatically than another. I just keep trying lots of things in the hopes that something catches fire.
What do you see as the biggest obstacle to overcome when you self-publish?
For many authors, the answer to this question would be marketing. Most authors hate marketing and just want to write. I happen to enjoy both, so that’s a definite advantage.
For me, I’d say it’s the stigma. Despite there being a ton of high-quality self-published books, many people equate “indie” with “low quality.” Let’s be honest: some of them are. Having spent a decent chunk of time in these self-publishing Facebook Groups, I can say with utmost certainty that a lot of people who don’t think they need professional editors really, really do. But for those of us who did work with professional editors, there is often no discernible difference in quality between indies and traditionally published books.
However, getting your book on bookstore shelves can be a real challenge for indies. I’ve approached several bookstores here in Paris and been told at almost every stop that they don’t carry self-published books. Some persistence (and a great book cover) can occasionally turn a no into a yes, but it universally has started out with a no, in my case.
That said, the economics aren’t particularly interesting for an author like me to be in bookstores. I make less than one dollar/euro per book sold in a bookstore, if the books are ordered by the store through Ingram Spark. For me, the most profitable sale (other than selling direct) is a Kindle sale, for which I earn 70% commission (with Amazon having exclusive rights to my e-book sales.) For a paperback sold via Amazon, my commission is 35% (due to printing and shipping costs). Having your book on a bookstore shelf is certainly a proud moment, but it does next to nothing for your bottom line.
Finally, what is something you wish someone had told you about self-publishing before you started?
There’s a lot to learn when you’re self-publishing, especially when it’s your first book. Writing is the easy part. After that you have to edit, format, pick a trim size, set your price, design a cover, typeset, register your copyright, get an ARC team in place, start building buzz/an audience, and much more -- all before you sell a single book. The process is long, time-consuming, and can be expensive if you’re working with quality professionals.
Then you have to learn how to write a book description (which is way harder than writing a whole book), pick your Amazon categories and keywords, set up Amazon ads, try to understand its mystery algorithm, market like your life depends on it AND start writing another book, because according to self-publishing industry experts, no one makes a living self-publishing until you’ve written twenty books.
Nah… scratch that. If anyone had told me that I might not have ever written my book, and I’m really glad I did.