After trying unsuccessfully to sell Boop and Eve’s Road Trip, debut novelist Mary Helen Sheriff was told her manuscript had three red flags that many other first novels have as well. Mary shares her experience with Zibby and other writers who may be facing publication roadblocks, as well as a few funky tips for anyone stuck with writer’s block. The two also discuss the differences between motherhood and grandmotherhood, how growing up in the 1980s and 90s affected the way they parent today, and which relationships in Mary’s life helped shape her characters.


Zibby Owens: Welcome, Mary. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss Boop and Eve’s Road Trip.

Mary Helen Sheriff: Thank you so much for having me. I’m super excited to be here.

Zibby: Please tell listeners what your book is about.

Mary: My novel is Southern women’s fiction. It’s the story of Eve, who is a college freshman who is struggling with depression. Her spunky grandma, Boop, gets wind of her struggles. When Eve wants to borrow her car to go find her missing best friend, Boop says, “Sure, you can borrow my car, but I have to come with you.” Boop’s goal here is, one, she wants to visit her sister in Savannah. Two, and more importantly, she is worried about Eve and trying to figure out what’s going on with her. Boop herself has a history of depression, and so she’s tuned into that. Most of the book is their road trip. It’s sort of a love story between a grandmother and a granddaughter. As Boop tries to help Eve deal with her future and finding herself and her authenticity, she also has to deal with her own past. Helping Eve helps her to do that.

Zibby: Excellent. Not to say that a mother figure can cause depression by any stretch, but I don’t think that Eve’s mom and Boop’s daughter helps the situation at all.

Mary: I agree.

Zibby: Tell me about this whole dynamic, which I feel like is very interesting, this alliance that forms between grandmothers and granddaughters and sort of skips over the more difficult party in between. What gave you the idea for this? Tell me about this particular piece of the relationship puzzle.

Mary: Boop is inspired my own grandmother. Her name was Hootie. She had passed away just a few years before I started writing this. I was still grieving, as one continues to probably grieve for people you love forever. I decided to base Boop off of her. My grandmother was a delightful, wonderful woman and a wonderful grandmother, but she wasn’t a great mom, mostly because she struggled with alcoholism and depression. That kind of made her an absentee mother, for the most part. When my mom was a young mother herself, my grandmother’s house caught on fire. Her husband died. She decided to move in with my mom and reinvented herself and became the woman I knew who was just wonderful, I couldn’t have asked for a better grandmother kind of person. To hear my mother and her sisters talk about their mother growing up, it was not the same person that I knew. I was fascinated by that ability to reinvent yourself. Then at the same time I was writing this, I was a young mom. I was kind of struggling with how to parent my own children. I grew up in the eighties. Kids had a lot more freedom, I feel like, than they do now. When I was young mom, I felt like the world was telling me I needed to be helicopter-y, but that didn’t quite sit right. I was really struggling with where the right balance is between taking care of my children and protecting my children, but then also letting them fall down and make mistakes and grow from those mistakes.

I think that Justine, who is helicopter extreme, is sort of my worst fear of the kind of mom I might become in my quest to want to protect my children. What happens in this story is that Justine is trying to be the mom her mom wasn’t. She goes to an extreme level. Her mother was absent. She felt like she raised herself. She wants to make sure that she doesn’t do that to her daughter, and so she overdoes it. She micromanages her whole daughter’s life. As a result, when Eve leaves for college, she doesn’t have the coping mechanisms to deal with life’s normal problems because she’s used to her mother just creating this perfect little bubble around her. That’s pretty much where Eve starts to fall apart, is just not having the skills because she hadn’t really had to develop them over life. There’s lots of tension between Eve and her mom and between her mom and Boop. There’s secrets and choices that they’ve made to not tell each other things that have made them misinterpret things and caused them to wonder whether they were loved and all kinds of important questions that haven’t been answered because they’re not being honest with each other in an attempt to protect themselves and maybe to protect each other too.

Zibby: Wow. Can we go back to the fire? Do you feel comfortable talking about that? Can you tell me more about it? That sounds horrific.

Mary: My understanding is that my grandmother was alone in her house. She fell asleep and maybe passed out. Her house caught on fire with her in it. Someone came in and got her out. The house was gone. She was okay. No one was hurt, but the house was gone. Their stuff was gone. All of the photographs that they’d taken over the years were pretty much gone. Back then, you didn’t have digital backup of anything. The photographs that she had of her family and stuff were people like — her sister might have had them. Somebody else had them. She kind of had to recreate stuff.

Zibby: So your grandfather did not die in the fire?

Mary: No, he had a heart attack.

Zibby: Oh, no. It is so interesting, this ability for grandparents to have a do-over, everything, make up for the sins of the past with the doting in the present.

Mary: I think there’s a freedom in being a grandparent because the responsibility isn’t completely on your shoulders. I think you’re able to be a little freer and more forgiving and more accepting of the mistakes your grandchildren are making. Your perspective on life is a little bit more balanced, perhaps, than especially young moms. I think that’s just a really hard time to try to define yourself as a mother. My kids are now in middle school. I’m getting a little nervous about high school and exactly how — that’s a different kind of parenting than I’ve had to do. We’ll see how that goes.

Zibby: I’m in the same boat. We have two almost-eighth graders now and also some little kids. I’m like, okay, so now I talk in a different voice. Even how high an octave I speak drops over time. I literally have a different voice with each of these.

Mary: They are able to think through things and make choices. You have to give them some freedom to do that even if those choices aren’t always the best.

Zibby: I loved what you said earlier about this need to helicopter, how that was of the moment and you didn’t buy into it. It does feel, also, like there are these parenting trends, if you will, and sea changes. Even though a few years before that was not the thing, now that it is the thing, you have to do it. It’s like, well, what? What happened to what I had to do three years ago? No? We’re done with that?

Mary: It’s different. I remember thinking, is this because of where kids — you remember how all the milk cartons had the pictures of the missing children on them?

Zibby: Yes.

Mary: You’d have your cereal at breakfast. Is this the result of a lifetime of looking at missing children on milk cartons? Then you’re now a parent and you’re just worried your kid’s going to get kidnapped all the time. I am not saying no one ever gets kidnapped and bad things don’t happen, but I don’t feel like they happen with the regularity that we fear they do.

Zibby: Or one could probably argue that they don’t happen because of the vigilance.

Mary: Could be true too.

Zibby: You never know.

Mary: Which came first? I think everything has its pros and cons. It’s all about balance and that push and pull and trying to figure out the right spot. That’s hard.

Zibby: Essentially, I feel like why there are so often these headbutting incidents between generations is because we all have to embrace those trends. When my mother or my grandmother says something and I’m like, no, no, no, everyone has to, say, breastfeed or whatever, whatever it is, they’re like, we didn’t. I’m like, well…

Mary: You did it wrong.

Zibby: Right. I think it all comes from this place of deep insecurity. Ultimately, none of us know what we’re doing because we can’t possibly know. It’s new to everybody. It’s constantly changing. You have to be very strong in character to go against the mold and be able to justify it because there’s so much data all the time. Whatever the collective has picked, there’s data.

Mary: Yes, you can find data, probably, to support a lot of different choices. Even if one thing is better in a certain way for your kids — maybe helicopter parenting makes your kids physically safer, but maybe it makes them mentally less safe. How do you find that space between, my kids are relatively physically safe and relatively mentally safe? It’s not the same for every kid. It’s the not the same for every parent. It’s not the same in every community. It’s a really hard thing to figure out the best way for you to parent your child in your times.

Zibby: It’s so true. Maybe as your kids have gotten older, as we have alongside them, I feel much more confident now making choices that I didn’t feel like before. I do think that having people like Boop in your life or people who have made different choices or who are so individualistic helps, to see that role model, to have it out there.

Mary: Right. You don’t necessarily have to do what everyone else is doing. It’s good to think about what everyone else is doing and what the thought behind that is and why that might be appropriate in some cases and not other cases. We do a lot of judging parents for the way they do things. That feels awfully unfair and hard on each other too.

Zibby: Totally. I do also feel, though, that there is this piece of feeling a little left out by the mom in the sandwich of the daughter and the grandmother. I don’t think my mother would say this out loud. Maybe I shouldn’t even say this. I was super, super close to her mom. I would be like, “I’m going to visit Gadgi.” She’s like, “Wait, you’re taking a whole trip now to visit your grandmother? What about visiting me?” She would never say that, but you get it. Then I wonder, is that going to happen to me? Am I going to bypass my daughter because I’m so obsessed with her daughter? I don’t know. It does create some sort of almost, not competition, but exclusion like you’re back on the playground again.

Mary: I think there’s a natural tension between mothers and children and maybe even especially daughters. I think that we feel some responsibility for how they turn out. In the same way we might be hard on ourselves, we tend to be kind of hard on our children. I don’t think grandmothers feel that sense of responsibility for how they turn out so much and see themselves more as a friend figure. That makes it a little bit easier. It’s nice to have somebody in your life like that who just loves you unconditionally and isn’t putting a whole lot of pressure on you to be who — your parents think you should be somebody. That’s a reflection on them if you’re not.

Zibby: Very true. Wait, so tell me a little more about the writing of this book and how you came up with the plot, how long the whole thing took, and all of that. Then I want to hear about your other stuff that you do like your blog and all of that, care packages.

Mary: It took me about six years, probably, total, to write it. I started it when my daughter was four and was leaving to go to preschool five mornings a week. I’d had a part-time job up until then. I decided that the amount of money I was making teaching part time was really not the difference in our lifestyle. This had been a long-time dream. Maybe this was my chance to grab it. I spent the time that she was at preschool largely writing. In about two years, I had what I thought was a complete manuscript. I’d had a critique group. I was feeling really good about it. I sent it out. I just got form-letter rejection after form-letter rejection, which was great fun. Especially because it’s a form letter, you don’t even know what’s wrong. I don’t know if my letter just stinks. You don’t send that much. You send a letter and you send maybe five pages, maybe ten, maybe a chapter. It’s not much. What’s wrong? I don’t know. I found this writing retreat called the Algonkian Writing Retreat. It’s in St. Augustine, Florida, which is a spot in my novel. It was already a spot in my novel, coincidentally. Anyway, I went to this writing retreat. They kind of sold it as the tough-love writing retreat. They had six industry professionals there that you got to meet with for twenty minutes at a time, which is kind of unheard of. You got to give them your pitch. Then they told you exactly what they were thinking, which is both good and bad.

Zibby: I like that.

Mary: What I learned that day is that particular draft of this novel had three red flags. Basically, they all agreed they would never even read the first page after reading my cover letter because of these three red flags. Red flag number one, the book was originally set in the 1990s. That’s not contemporary and it’s not historical, so it makes it a little tougher because it doesn’t sit on a natural shelf. If you are a debut author, they do not like your book to be set — they’re like, 1950s or before or now. That in-between time makes them super uncomfortable. Now, if you’ve got a reputation and you write — that’s different. For someone, I’ve never heard of you, then that’s red flag number one. Red flag number two was — this is still a character-driven novel, but it was even more character driven in its first draft. This book is held together with the thread of, Eve’s best friend has sort of gone missing in action. They’re trying to find her. Before, that was a very small subplot in the whole book. The rewrite ended up pulling that storyline out to make that the arc.

The third problem was that it was in first-person point of view. My background was writing YA and middle grade. They love first person in that genre. Apparently, adult books sell better if they’re in third person. What each of these people told me independently was, with three things that we don’t like from debut authors, we wouldn’t read your book. Of course, you can think of a million books that break all of those rules, but they usually aren’t someone’s first book or they’re someone famous’s first book, which doesn’t have to follow those rules either. Interesting, I had been writing for a long time and I never knew any of this stuff. I’ve yet to see it written down anywhere, but that was apparently the thing. I spent a few months grieving for the loss of this book that I thought was great. Apparently, it wasn’t commercial enough for an agent to be interested in it. Then I put on my big-girl pants and did a massive rewrite. Changing the time, adding a plotline, and changing the point of view, in particular, was huge. This draft that resulted from that is way better than the draft that didn’t sell. Do I regret it? No. Was it hard to do that? Yes. That’s the journey of that book and its rewrite and why it took so long and all that good stuff.

Zibby: Wow, that is so interesting. I have not heard those things either about debut novels. Who were the insiders? Did they work in publishing houses? Were they agents?

Mary: They were agents. Some of them did more TV. One of them was a book-to-TV kind of guy. The others were agents. Three agents, one TV guy, and a Pulitzer Prize author who wasn’t talking about that so much, talking about other stuff. The agents were the ones, in particular, who pointed this out.

Zibby: That’s so interesting. It’s almost like it could save authors a lot of time to go to a boot camp like that before they write the book. If you had only known…

Mary: Yes. I think that’s what he would’ve liked to do. This guy was thinking, you write your whole synopsis before you write the book, and that’s what you’re bringing with you. Most of us had already worked on our books and had already invested a lot of time into them. To then go and hear this was —

Zibby: — It’s also hard to have a fully formed idea without actually writing it. Maybe you need to write that draft to figure out what — things unfold as you write. It’s hard to see the whole thing from the outset.

Mary: Yes, absolutely. I guess some people think differently too, but I’m with you. I definitely learn my characters as I write them. The plot changes as I go. I always have an outline, but the book, in the end, is not what the outline was.

Zibby: How did you get started writing and publishing?

Mary: I was twenty-three when I wrote my first book. I was in graduate school to be a teacher. I had an assignment that went awry. It ended up being, basically, a novella, which was not at all what the assignment was supposed to be. I turned it in with a sheepish apology of, “You don’t really have to read this. I’m hoping that you’re just going to be excited that your assignment encouraged this to happen. I understand if I have to redo it the way I was supposed to do it in the first place.” The teacher was very gracious and was like, “This is awesome. I love it.” I really had so much fun writing that book. The professor said, “Hey, you know, you should try to submit this and get it published.” I was like, yeah, maybe I should. It was only like eighty pages, which isn’t a book, exactly. I did rewrite it. I tried submitting it. It didn’t really go over very well. To be frank, it was bad, so it’s okay that it didn’t go over very well. From that, I decided that I did really enjoy writing and I wanted to be a writer. I was teaching as my job. Over the summers, I got an MFA at Hollins University in writing for children and young adults because that’s where my heart was at that time. I’ve written two YA books and one middle-grade book that sit on my computer. Boop and Eve’s Road Trip was going to be a young adult book, but Boop ended up really being a dual protagonist. She has as much of the story as Eve does. You really can’t have an eighty-year-old be a main character in a young adult book even if the other person is young. I made Eve a little bit older when I realized that was happening and put her in college. In the original thought, she was going to be more like in boarding school or something like that, so younger but still away from Mom. Eve’s nineteen. Boop is eighty.

Zibby: Now also, you do your blog. You have these amazing literary care packages. Talk about those things.

Mary: I have a blog called The Gift of Story. One of the things I do there is something called a literary care package. I did one for your anthology.

Zibby: Thank you. Thank you.

Mary: My pleasure. Basically, it’s the idea of, people like to gift books, but sometimes it’s overwhelming to think, there are a million books out there. Which book do I give? What for? Who for? What I try to do is find a book that I think would make a great gift for a certain target audience, an example of your book being people who are mothers, and then come up with two items that are related to the book, usually thematically related to the book, so that you have something more than a book to give. A book is a lovely gift, but sometimes people want something to round it out a little bit. I call them literary care packages. I make one a month. Then I have a larger e-guide that’s twelve of them. Sometimes they’re related to a holiday or a particular event. If you’re going to a baby shower, here’s a great gift. If you’re going to a wedding, here’s a great gift. Then sometimes they’re related to a certain target like yours was. This is a great gift for moms whenever you might give a mother a gift. Obviously, Mother’s Day is a nice time to do that, but people have birthdays all year long. I do those. I also have a Facebook group called Bookish Road Trip which is for travelers and readers. We do lots of fun things there. Zibby is going to be our guest at our next book club, which is July 7th at seven o’clock. We’re going to be discussing Moms Don’t Have Time To: A Quarantine Anthology. We like to have the author come if they’re able to. We do a different book every month. It runs the gamut. It’s lots of different kinds of books. Last month, we did Stephanie Dray’s recent release of The Chateau Lafayette, Women of Lafayette, I’m mangling that, but a historical fiction book. We’ve done all kinds of different things. We like to have fun and chat about books. We do panels and lots of fun things.

Zibby: Amazing. I’m so excited for my book club, I have to say. Thank you for making me a care package.

Mary: I’m so excited to have you.

Zibby: or something. It’s amazing. Awesome. In terms of writing, you have all these businesses and writing and all this great stuff, are you doing another book? Are you on hold with the books for now? What are you thinking?

Mary: I am writing. I’m not writing as much as I would like to be. I am very much struggling to figure out how to find time to write and find time to market. When the book came out, the marketing sort of took over. It’s been hard to pull back enough to find large amounts of time to write. I’m writing about an hour a day, give or take, which is slow, but it’s steady. I decided to do something really strange this time with this novel. It’s very different from Boop and Eve’s Road Trip. It’s a dystopian novel set in the future. I was having trouble writing it because I kept writing ten, twenty, thirty pages and then realizing that’s not what I wanted to happen and throwing them away, which is not a very efficient way to get into a book. I decided to write a screenplay of it first because for me, dialogue comes the easiest. I thought I could just basically write the dialogue for the whole book and find the characters and find the plot. If I need to throw out a scene, whatever. That was maybe a half an hour of my time, not a big deal. I’m going to finish that screenplay this week. The real test is going to be in July when I start writing it in narrative form, whether that’s an easy transition. I don’t know yet. It’s an experiment. I’ve never heard of anyone writing a book this way. I kind of made it up. I’m crossing my fingers. The screenplay was easy to write, though. I’m not saying it’s the best screenplay. I’m sure a real screenplay writer would tell me lots of things that are wrong with it. As far as getting what I needed to do as an exercise, it’s kind of like a cross between a rough draft and an outline, essentially. It’s a hundred-ish pages. I’m hoping that I take the scene and I turn it into prose and it works beautifully. We’ll see.

Zibby: I love that. What a great idea. Also, it can be a movie. There you go. It’s already done.

Mary: There you go. I could have somebody who actually knows what they’re doing writing a screenplay fix it up.

Zibby: You at least have the bones of it, which is great. Awesome. That’s exciting. I love how your brain works, how you’re thinking about things a little differently. To your point on marketing, oh, my gosh, you can’t just have a book come out. It’s a whole thing. It never ends.

Mary: A whole thing. If you talk to these people who write four books a year, I don’t know how they do that. I don’t know. You’ve got another book coming out soon.

Zibby: I do. I know. I have a couple books coming out. I don’t know how I’m going to do it. I’m still trying to sell this book. I don’t know. I have no idea. In my head, I’m like, I’m just going to not make it as big a deal the next time. Already, I’m like, ooh, if I spend all weekend making this presentation, maybe if I sell it in this store, that will change everything. What if I do — you just can’t stop thinking about it, at least me. You can always do it better.

Mary: The truth is that selling books is hard.

Zibby: It’s really hard.

Mary: It’s not as easy as selling a lot of other things, I think. Even though they’re not an expensive product, there’s a time cost in someone buying your book too.

Zibby: Huge time cost.

Mary: It’s not just the twenty bucks your book costs. I’m also setting myself up to spend six hours of my life with this book. I think that’s the hurdle maybe more than the twenty bucks.

Zibby: Also, twenty bucks is a lot if you don’t know if you’re going to like something.

Mary: Right. True too.

Zibby: Sometimes when I’m scrolling on iTunes for a movie or something, I’m like, oh, gosh, I can’t rent this one? Forget it. I have to buy this movie? What if I don’t like it? What a waste.

Mary: That brings in the point of how important reviews are, which I didn’t realize. I was a reader for many, many years before I ever had a book published. I didn’t know that my spending five minutes writing a review for somebody was such a huge help to them, especially if they’re nice. Now I try really hard to write a review for books that I read. It doesn’t have to be some long, huge, four-paragraph thing, a short paragraph, a couple sentences, but it does make a difference. People who are scrolling through and never heard of an author, especially new authors, I’ve never heard of you, I don’t know if I want to invest twenty bucks and six hours of my life into what you’re writing, having people say, hey, yeah, I did do that and I don’t regret it, you should too, it really helps.

Zibby: Very true. I know. I’m writing this memoir now. It’s getting long. I’m like, oh, gosh, I feel so bad asking people to spend all their time reading this. This is a lot of time. I wonder if I could sum this up or something. Maybe I should put cliff notes at the end of each chapter or something funny. If you don’t feel like reading this chapter, here’s what you missed.

Mary: You could do a Choose Your Own Adventure. Remember those books? There was like twelve.

Zibby: Yeah, I loved those. Do you have any advice for aspiring authors?

Mary: My biggest advice is to make friends with other authors. I think no matter what stage you are in your career, you can benefit immensely from those friendships. If you’re new, learning the ropes and helping someone with your craft and doing critique groups or beta swaps or that kind of thing can really be helpful. Then as you move along, having someone introduce you to agents or publishers or other book influencers can open up lots of doors for you. Then the emotional support, which should not be overlooked, I don’t think anyone who doesn’t write books understands how hard emotionally this experience can be. Having people who have been there and done that and can say, “Hey, yeah, that stinks. Now put your chin up and keep going,” is really helpful.

Zibby: Very true. Yes, it doesn’t get easier being rejected. It doesn’t matter how old you are or how much time you’ve invested. If someone doesn’t like what you’ve done, it really stinks. Not fun.

Mary: Even constructive criticism, which is helpful and helps you grow and get better, it can still also be a little bit of, ooh.

Zibby: I’m like, I should really show this draft to someone, but maybe I won’t.

Mary: Maybe I’ll wait a little while.

Zibby: Then I won’t be done. Anyway, so nice chatting with you. I’m so excited to come to your book club. Thank you for all of your support of me along the way. Delighted to chat with you. Just so glad our paths have crossed.

Mary: Thanks so much. It was great to finally get to interact one-on-one with you.

Zibby: You too. Have a great day, Mary.

Mary: You too. Buh-bye.

Zibby: Buh-bye.


BOOP AND EVE’S ROADTRIP by Mary Helen Sheriff

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