Esty Heller: intentionality, logistics, and the inevitability of gray area
Released just before Yom Tov, Follow Me is a vibrant story of travel, food, and connection. In an intertwined dual-plot, two very different women uncover the loneliness they’ve been avoiding and find new possibilities. Esty Heller masterfully balances light reading with meaningful character development and thoughtful themes, a combination that is surprisingly uncommon and so satisfying when achieved.
Esty Heller writes fiction, humor, and personal essays for Mishpacha and Family First. In addition to Follow Me, she published Yardsticks in 2021.
How did writing, publishing, and receiving feedback from Yardsticks inform Follow Me?
Although Yardsticks was my first book, it wasn’t my first writing project. I wrote my first serial for Mishpacha, Money Talks, seven years ago. I went into it blindfolded, and I admit that it was a reckless decision. It was during a busy time in my life, and I had three weeks' notice. I kind of closed my eyes and jumped in. I'm happy I did because it gave me the kind of experience I would never have acquired had it been a rational decision. By the time I started working on Yardsticks, I already knew what I was getting into. So why did I do it? I guess because I'm a glutton for punishment. Living with the stress of a weekly deadline is harrowing, and it took me a few serials before I learned to enjoy the work.
My next serial, Follow Me, was definitely a lot easier than Yardsticks because I’d gained experience inof how to properly structure a serial, with the pacing, development, and plotting. Usually, when an idea strikes, my default is to start writing immediately. But that’s the wrong approach. I worked hand in hand with my editors, Bassi Gruen and Avigail Sharer, and learned to force myself to spend a lot of time plotting. They were incredible; I could never have done it without them.
It's so interesting because writing is such a creative type of thing, but you describe it like a science where you're getting that technique down pat.
You need to have both; it's a balance. There's a lot of math to it, things have to make sense and you constantly have to figure out logistics. A character appears, and then you never mention him again. Where did he go? The first thing I do when I start a serial is create a character spreadsheet. Every time a new character appears in the story, I add him or her to my spreadsheet, along with relevant information. I constantly refer back to my spreadsheet to make sure every character’s behavior matches his profile. I also keep notes of various running conflicts, because sometimes I’ll start a sub-conflict and later forget about that thread. That’s a literary crime – Chekhov’s Gun. A good editor will never let a detail get lost: if you’re mentioning it, it has to be necessary, and if it isn’t, cut it.
A mistake or contradiction hits a reader much more glaringly than the editor who was involved behind the scenes. That's why the editing process and self-editing are important. You constantly have to step back and re-read to see that whatever you did so far makes sense. Making sense is a biggie, I'm obsessed with that. So all these different things are more like discipline and the logistics of it. It's not enough to have an interesting idea or a cool character, all these details have to line up.
I hate doing the plotting, but I have to. For the past week and a half, I refused to write a single word before plotting out every last scene of the story I’m currently working on. It's slow progress and very intense. I start with a scene, deciding that this and that will happen. Then I tell myself, no, that's impossible. It can't work because XYZ. So I go back and shift it. The chronology has to make sense. A character has to be in a happy mood when this incident happens, or she has to be full of anger when that’s happening, and therefore, this scene has to come before that one, but then that detail has to move over to three chapters later. Or earlier. It's dizzying, and it takes a lot of concentration.
After the first few chapters, you panic, what did I get myself into? You desperately want to back out. And then it happens again at the 60, 70% mark when you have no idea how to resolve everything. But when it's flowing, when you go from chapter to chapter with your creative juices turned on, it’s exhilarating. One thing I’m always firm about is my insistence onof staying at least ten chapters ahead of the reader at any given time. Not all writers work this way, most serial writers live hand to mouth. I don't know how they do it, I wouldn't be able to sleep at night.
Yardsticks and Follow Me are centered around an “everyday”ness that makes for a fun, low-key read. The scenes are so regular, with no extreme or exotic scenarios or “problems”. What challenges does this present in keeping the plot moving?
My father wrote many thrillers, he goes by the name Eli Shekhter. I’ve never done anything like his stories. I don’t have a wild imagination, I rather like to explore different characteristics and conflicts.
But sometimes I do feel like, could we get out of the kitchen? Could we shake things up? Changing up a setting is often a solution, just take these characters somewhere different. If a character has a unique trait or career, something within that career could take them to different places. In Follow Me, we got into the whole touring industry and that took the characters over the world. I also took Pessie Hersko to Israel for two or three chapters to change the setting.
I also like adding interesting characters to make things colorful. They don't have to be carnival jesters, they can just be neighbors on the block. In Yardsticks, I used Yelena as a main character, the kind of person people usually pass by without giving her any thought; she's just the Russian seamstress. By turning her into one of the main characters, we explored something different without having any guns drawn.
Despite the fun and easy tone, your writing has a seriousness of layered themes. Not just talking about materialism, but about how ideals collide with reality. Or not just talking about the facade of social media, but about how our inner insecurities spill over. Your epilogues make it clear that your step 1 is the base theme. What’s that process like of developing a stack of themes that play into each other and make every chapter thought-provoking?
I started Yardsticks with this one line in my head: principles versus loyalties. What happens if a person is put into a position where her loyalties are set against her principles, what she stands for vs who she needs to side with? So I had Mina and Yocheverd, two sisters with very different principles, and being sisters, Mina had to be loyal to Yocheved. Throughout the entire story, those two strong elements were in conflict. It kept coming out differently, and then they had to compromise on one to appease the other. Of course, there are external conflicts as well, but once you start having people involved in that conflict, you start understanding all the dynamics and why people make the decisions that they make.
I was determined not to hit readers with the message, “Spending a lot of money on a wedding is wrong.” I tried keeping it open-ended, raising the voices of all sides, and leaving the reader to think about it on her own. Although there is no one answer, there’s definitely place for a discussion.
Nuts and Basil as Deena’s social media personality is millennial, cool, and current. Were you concerned about losing an older audience or those not familiar with the ins and outs of social media?
It was a concern that we discussed. It was more concerning to me than the general readership because social media a big no-no in my community, our Rabbanim are extremely against it. So I can't say that I have an unbiased opinion on this one. But when I set out to write a story, my editors and I agreed that we're not coming out with a message that social media is bad because of hashkafic reasons. Instead, I focused on universal elements, the emptiness, and false satisfaction. Deena was constantly trying to fill up on that good feeling, it was like a numbing agent in her life. And sometimes, she didn't even appreciate the popularity, she was repulsed by herself. She would meet some of her followers and cringe inside at how she was constantly being scrutinized.
Loneliness is such a deep and touching topic, something that takes a level of self-awareness to recognize that’s rarely seen in fiction. You took on a few different aspects of loneliness and connection in Follow Me. How do Deena and Pessie’s experiences bring understanding to each other, while presenting a more nuanced look at the subject to readers?
When I set out to write this story, I had one scene in mind, where three very lonely women from very different backgrounds meet up. Each of them experienced their loneliness differently, but they connect because they’re able to identify with each other’s pain. Such a scene is quite universal; sometimes you're going to find yourself relating to someone extremely different because of your universal pain points, and that itself is such a strong comfort, it gives a person a tremendous support system and it makes them feel better.
Pessie Hersko lives a sheltered life, so different from Deena's out-there personality, which heavily revolves around social media. Deena is a whole celebrity, and Pessie wouldn't even know to appreciate it. Yet they clicked from the first second they met because they were able to connect on that level of loneliness that they were both experiencing.
Characters are human. You try to put some lifeblood into them, and they will go down a path to address their conflicts. They're going to meet the people that they need to meet. But the whole backstory also has to make sense, connecting the characters and leading up to their climax. I find that challenging because you don't want it to be contrived and feel like a parallel journey with everything together. So right when you're leading up to the climax, their conflicts will overlap and the ends come together.
Your writing is consistently about gray areas and coming to terms with the realities that might cool down raw idealism. Rereading both of your books back to back, two scenes stuck out at me. In Yardsticks, Mina is representing a minimalist ideal while spending her days in the world of luxury and wishing the same for her daughter. In Follow Me, Pessie finds herself defending the new tour-guide lifestyle, while she is still furious and terrified of what it will bring. These mirror-image scenes made me wonder: How is the natural process of coming to terms with the gray areas in life affected when we need to defend and present ourselves to the world?
Sometimes being forced to view something differently opens your eyes to the right thing. You verbalize something, then stop and think about what you’d just said. Maybe Pessie was telling her mother all that she told her only to defend her husband, but she used the words she herself needed to hear. Before that, she wasn't in a position to be able to think why her husband was doing what he was doing and why maybe for him it's the right thing to do and why for her the right thing to do is to be supportive and go along with him.
But it's not like I intentionally always put myself into this boat, with the gray area. It's hard, why did I put her into such a sticky situation, now I need to get her out of it! It's easy to create problems for your characters but extremely difficult to resolve them. Whatever she's going to do now will be wrong, so it can’t be black and white.
And that's such a good point because something that comes across so strongly is how relationships and our inner struggles are complex and don't fit in a box. And as much as she might have compartmentalized, they keep spilling into each other and affecting the different areas of her life in ways that she wouldn't have predicted to be connected.
Behind the everyday writer of these books lies dozens of humor articles that you write for Family First. Tell me about writing those, and what that kind of writing does for you.
When I started writing, I wrote very heavy or sad stories of people in horrible life situations. The most common feedback I got from my readers was that they cried. Over the years, I’ve seen the shift where people started telling me, “I laughed, I was rolling.” I like that feedback better because life is so heavy and intense, everyone has to put up with so much pain and suffering. When you read something and get lost in a different world, just let it be an enjoyable, pleasant world. Make people smile. I found it so interesting when my editors started requesting humor pieces. I'm this heavy, intense person, I was always the serious kid, the nerd. Why are you asking me for funny stuff? But I realized that what they saw in my writing was more satire than humor, and writing satire somehow came naturally to me.
As my writing style developed, I realized that humor will pop up all over my writing. Even when I'm writing a serious piece, the characters are going to say unexpected things or a blunt statement and that will make readers laugh. It's not a tickle, tickle joke, it's just the unexpectedness that makes you laugh. So you can have a balance. You can have a serious message in a funny piece, and you could use very light language in a serious piece.
What frum books have you recently read that you can recommend?
I love reading historical fiction, probably because I can't write it. I recommend anything by Leah Gebber. Rocking Horse and Map the Starlight are masterpieces. Also, M. Kenan’s Wildland is a phenomenal book. It's different from my typical writing and reading style, so I was surprised at how much I enjoyed it. It has a really strong plot, and most stories these days are more situational than plotty. I also enjoy all of Riva Pomerantz and Dov Haller’s books. I always think of Dov Haller’s books when I'm writing. I don't reach his toenail, but I try for that relatability.
Great interview!