Interview with Ashley Winstead

Author Series #1

Today I’m so excited to share with you the first part in a semi-regular series in which authors share with us their trials and tribulations, mountains and valleys, high points and heartaches in the ever-changing publishing industry. 

Our first author is Ashley Winstead, whom I met a couple of years ago at an event at Murder by the Book in Houston. Afterward, we grabbed drinks at a popular hangout across the street (Under the Volcano serves great margaritas and tacos!) and shared industry insights and the behind-the-scenes things that authors aren’t posting on their social media feeds. 

From our very first conversation I came to appreciate the savvy eye with which Ashley analyzes the industry and the intentionality with which she approaches her writing and her career. Ashley knows what she wants and goes for it, barriers and glass ceilings be damned. She’s an inspiration, and I am confident you’ll learn from her in today’s interview. Also, side note: she’s actually Dr. Ashley Winstead with a Ph.D. in English!!

Quick Personal Update and Reflection: This week I celebrated twenty years of marriage to my husband Tim, and as I was thinking about how much has changed over the course of our two decades together (kids, pets, jobs, degrees), I also thought about the mantra that has made us work. Here are the two words I would use to summarize the secret to our first twenty years together: low expectations.

The idea that we both have low expectations (and thus, happiness) has become a recurring joke between us. Certainly, we have high expectations where it counts: fidelity, efforts to communicate, spending time together…for all of that, our expectations are high. But, for the other things—taking elaborate trips, planning romantic date nights, buying each other anniversary gifts (or hey, remembering that the date has come and gone)—that’s where the expectations are lowered. Part of this lowered bar is likely a survival instinct from having three under three around the ten-year-mark, and the other part is that our personalities lend to enjoying simple things like grabbing a to-go meal and watching a movie rather than dressing up for a night out. 

I’m beginning to realize that part of being content in publishing is also lowering my expectations.

• My first novel sold at a three-way auction within two weeks, but my fourth novel has been on sub for a few months.

• My third novel hit a bestseller list, but who knows if that will ever happen again?

• I was able to go part time two years ago, but because my daughter is starting private school, I’m looking at signing a full-time teaching contract for next year.

  Change in life and in the industry is inevitable, and, as I heard Jami Albright say recently on the Wish I’d Known Then podcast, you either keep going or you stop writing. I’m the kind of person (at least in this era of my life) who has to write, so that’s my answer. My agent recently told me that it’s harder right now for an established author with 3-4 books (but no huge breakout) to get a deal than for a debut. BUT, I also know aspiring authors are sitting in limbo for months at a time. I’ve had to learn to be okay with the changing publishing landscape, to embrace joy in other areas of my life, and to wait patiently. 

All that to say, who knows what happens next? But, I hope that you will find as much comfort and knowledge in Ashley’s post as I did, and if you’re waiting, know that you’re not alone.

As ever, you can find info about working with me as a book coach at www.kristenbird.com

Now, onto our interview!

Ashley Winstead

Can you tell us about your debut novel? 

Ashley: My debut, In My Dreams I Hold a Knife, came out on August 3, 2021. I received a small advance for it and a second novel in a two-book deal, and I knew at the time that it was a small advance, but I was feeling nothing but grateful to be published. I received great marketing support because the Sourcebooks Landmark PR & marketing team is really good at what they do, but in no way was IMDIHAK a lead title. No one has ever explicitly said this, but I suspect the popularity of the book was a surprise to everyone. Once it started gaining traction with readers, my publishing team took note and opportunities started to snowball. I say all the time that early readers have the power to reshape the fate of a book, and I really mean it. I watched it happen.

How many novels have you published since then? Have you ever changed publishers? What differences have you noticed in the publishing experience with these later novels? 

Ashley: I’ve published four novels since then – two more thrillers (The Last Housewife and Midnight is the Darkest Hour) and two romantic comedies (Fool Me Once and The Boyfriend Candidate). Since Sourcebooks was really focused on building my thrillers, we ended up working with Graydon House, an imprint of HarperCollins, on my romantic comedies. 

I really liked the split, actually – in the early days as a multi-genre writer, I felt working with two separate publishers kept things clean. It was fascinating to see how another publisher operated, and be able to compare my experiences not only publishing in romance vs. crime fiction (I’ve learned a lot about the similarities and differences in these worlds and readerships) but also working with a Big 5 versus an independent publisher. 

It was also interesting to essentially start over as a debut in romance at the same time that my thriller career was building. As a debut you do a lot of introducing yourself so readers have the chance to get to know you and get a sense of what you might bring to the table. Doing that, while trying to keep excitement alive with my thrillers, ended up being a lot of balls to juggle. Not recommended for the faint of heart or anyone who wants to hold onto any scraps of their ego.

Have you ever had a novel ‘die on sub’? At what point in your writing career did this happen? How did you handle that (emotionally and/or practically)? 

So far I haven’t, but trust me, I’m knocking on every wooden surface. I know this happens to almost everyone at different points in their careers, so I’ll likely never feel safe. An experience I had that was similar to dying on sub was that the first book I ever wrote, a YA contemporary fantasy, landed me my wonderful agent, who then sent me a ton of suggested edits. It took me a while to process those substantial suggestions because I’d just been through the ringer editing that manuscript in Pitch Wars (RIP). 

After about a year (yes, that long), I returned to the book and dove into the changes and really ended up loving the rewrite. But when I sent it back to my agent, all hopeful and excited, she still didn’t think it was in a state to go on sub. That was a low point for me—I didn’t know what else to do to the book to make it better, and obviously if your agent doesn’t want to take your book out, you either shelve the book or the agent. The latter wasn’t on the table for me, because I love my agent. So I basically buried the book in the bowels of my laptop (I’m being dramatic—it’s just in a file like everything else), mourned that those characters would never see the light of day, and moved on. I guess you could say I died on pre-sub.

What has been the best part of publishing? The worst part? Or, what has been your highest high and lowest low in publishing? 

Ashley: Oh, man. You know you’re a writer when you can enumerate all your many lows but struggle to think of the highs. Not because you haven’t had them, but because your masochistic brain lovingly collects the lows and tends to them like a precious memory garden, and yeets the highs out days after they’ve happened. This might be best answered in list form.

A random assortment of lows from a much longer list:

1. The aforementioned YA fantasy dying on pre-sub.

2. In My Dreams I Hold a Knife struggling to find a publisher for the first few weeks it was on sub. I might’ve cried in a hotel room in Austin before wiping my tears and trying to smile through a weekend-long work conference.

3. The time I did a virtual event and only my mom and my sister showed up, but the bookseller didn’t realize our only two attendees were related to me, so we did the whole shebang anyway.

4. Actually, pretty much any Zoom or digital event where less than 10 people show up and I’m racked with guilt that I didn’t draw more of an audience.

5. That time my favorite romance writer said yes to blurbing my debut (much excite!), then ghosted me (much sad). I agonized for months over what I did wrong until I realized it might not be about me. (Or it might be. Jury’s still out.)

Highs (one more than the Lows because I’m an optimist):

1. Seeing my name on the list of writers accepted into Pitch Wars. I made my husband verify because I wasn’t sure that I hadn’t hallucinated the sight out of sheer desire.

2. Getting my first book deal for In My Dreams I Hold a Knife (thank you forever, Shana Drehs!)

3. Each subsequent book deal. I’ve celebrated each with sparkling rose and a fancy dinner at my favorite restaurant in Houston.

4. Discovering the thrill of Bookstagram. What was I doing with my life before it?

5. Meeting readers at my first in-person events, which didn’t happen until late 2022 thanks to the pandemic. Despite my high awkward levels, meeting readers makes me positively giddy (and nervous, but mostly giddy).

6. Getting certain rights news that can’t be shared yet. (Evil, I know, but that conference call was truly too wonderful not to include here, even in vagueness.)

Would you consider other types of publishing (indie, hybrid, digital first, Kickstarter)? Why/why not? 

Ashley: I have one (1) single talent, and that is writing novels. (Let’s pretend for the purposes of this that I don’t question whether I’m actually talented at it every other day.) Everything else that you’re required to do in those other types of publishing—learn metadata and search engine optimization, PR, marketing, light economics to know when to discount your books, etc, etc—is beyond the scope of what I want to spend my time doing. I have enormous respect for everyone who takes a path that isn’t traditional pub. Those authors are their own team on top of being the talent, and damn, that’s hard work. That’s why I love to see indie writers find huge breakout success. It always makes me whistle to myself, like my God, you achieved the dream all on your own? It restores my faith in the old idea that books that readers genuinely like will find success, even with the odds stacked against them. That gives me hope.

Do you think of yourself as a full time writer? Do you have other streams of income that help pay the bills? 

Ashley: I am a full-time writer, for which I’m very grateful. Real talk, my other income stream is my husband, who also has a full-time job that provides me with health insurance. (I resent that my insurance card and Health Savings Account card both bear his name because I’m a bitter feminist and don’t like being anyone’s dependent.)

What would you tell someone/what advice would you give to someone who wants to be traditionally published? 

Ashley: You’re not done trying until you say you’re done. When I look around at which writers end up getting published versus the ones who don’t, the difference-maker isn’t talent. It’s a little bit of luck but overwhelmingly sheer persistence. Rack up those rejections. Don’t take them to heart. Write as many books as it takes to get your one yes, and then the next yes. If you’re full of anger and resentment and spite over it, excellent. Use that as fuel.

What does success in publishing look like to you at this point in your career? Has it changed over time? 

Ashley: Like any Type-A eldest daughter worth her salt, I’m ambitious and impatient. My vision for success hasn’t changed much from the beginning. In the immortal words of Florence and the Machine, “I never wanted anything from [publishing] / Except everything [it] had / And what was left after that too.” Colleen Hoover- or Sarah J. Maas-level success would be just fine with me. What has changed over time is my patience. I’m learning to make peace with keeping hope alive over the long road. 

Is there one thing you or your publisher did that you think may have helped sell books to readers? We love tips and advice! 

Ashley: I credit early readers on Bookstagram with In My Dreams I Hold a Knife taking off the way it did. The fact that early ARC readers got excited about it and created buzz for the book was everything. So anything you can do to actually get ARCs or digital galleys into readers’ hands can be a huge win.

Do you have any tips for protecting your mental health in such a tough business? 

Ashley: Here’s what works for me. I’m incredibly invested in my writing, but I’ve been able to emotionally disinvest from the politics and social tensions involved in the publishing industry. (To be clear, I’m not disinvested in calling for more equity, author/publishing employee protections, and the like—not that kind of politics. I mean the he-said, she-said, so-and-so-is-going-here-and-saying-that kind of politics. Simply put, I stay in my corner and don’t engage in drama that isn’t about justice.) 

I’m also on a journey of disinvesting from the market side of publishing—I’ve gone cold-turkey with review sites like Goodreads, don’t look at my portals to monitor sales outside of two times a year when royalty statements come out (and then you best believe I’m scrupulously checking to make sure all is right), and have learned to reject the idea that the amount of money paid by publishers for a book has any relationship to the quality of said book. All of those things are really good for your mental health. Just to be clear again, I’m not advocating for authors to not engage in the business side of publishing—every author is an entrepreneur and should treat their business with seriousness. 

What I’m saying is not to obsess or equate your sales numbers with your self-worth. Do your due diligence and then get out. I’ve watched too many writers drive themselves into depression obsessing over numbers. On a totally different note, I long ago decided that it’s important to me to be true to myself (A Genuine Golden Retriever Personality) and be a welcoming person to everyone, even if they don’t reciprocate. I’m not doing it for reciprocation, and I’m not trying to be the coolest person in a room, so if I go out on a limb and try to be friendly to another author or a reader and they’re not nice back, no sweat. Nothing lost, because all I’ve done is be true to myself, and everything else is out of my control.

Lastly, leave your ego at the door. In an interview about why she paused touring, Miley Cyrus said the intense experience of being observed so often—of being an object that subjects were constantly watching—was toxic for her ego and got in the way of her having normal relationships with other people. While most writers will never experience this to the extent that Miley Cyrus does, there is something to be said about the puffing up your ego has to do to be able to sit on a stage and talk about yourself at book festivals, or sit in a signing line to meet readers. 

Make sure you’re always deflating that ego after you’ve accomplished what you need to do. Otherwise, you run the risk of not only being a jerk, but getting in your own head about what you’re owed. Again, I’ve witnessed this sink other writers. If anyone needs tips on deflating your ego, it helps to remember one of your more embarrassing moments. Like yes, you wrote a good line some people have highlighted in their books, but you’re also the person who accidentally drove her car into the dining room when she was 16 and very sleepy thanks to undiagnosed mono. Chill out!

Thank you, Ashley, for sharing your wisdom and insights. Check out Ashley’s latest thriller, Midnight is the Darkest Hour, and follow her on Instagram at @ashleywinsteadbooks.