Three Questions with author & editor Jessie Gaynor

The Literary Hub editor and author of THE GLOW talks about funnies & jokey asides, pitching tricks, writing production, and the brief elation of publishing a book, & more!

For this month’s three questions, you’re getting a little insight from the witty, wonderful mind of Jessie Gaynor. Jessie is, on my massive brain spreadsheet of editors, one of the people who never felt like there was some weird email wall (PR wall?) to be broken and instead, I was able to just shoot the shit from the hip with her really early in our exchanges. It always works better for me to be quirky and personable in emails (especially when I make a mistake), but I get more responses when I’m in fact NOT a BOT-VOICE. And throughout the last year (?) I found myself emailing Jessie about our (tumultuous) family vacation, flying toddlers, epic colds, all the things that you might talk blankly about with a friend.

And so, (am I allowed to say this?) she’s one of my favorite editors in the industry. She’s also really good at tightening an essay and making it look easy.

And for the BIG STUFF, she happens to be the author of THE GLOW (which got its own glow in the New York Times, Elle, Shondaland, Grazia, Glamour, Woo, CrimeReads, and more, and is a book I secretly hope Gwyneth Paltrow and Emily Weiss both have on their night stands,) and she’s an editor at Literary Hub. You can buy The Glow in paperback now too, and you should!

Jessie Gaynor © Ebru Yildiz

How do you manage the brain clutter of being both writer and editor (and mom!)? How do they complement one another and how do they clash (if either)?

The biggest thing for me is that I have to write in the morning, before I start my editing work. As an editor, I really try to inhabit the voice of the writer whose work I’m reading. It feels important to make suggestions that hew as closely to the author’s intention as possible—to push them to write the most clear and compelling version of their own stories, in their own unique styles. I never want to make suggestions based on what I, the writer, would say.

And after spending a day bouncing from voice to voice, it’s difficult to return to my own.

I’m very fortunate to have a partner who supports that need—in the mornings, he gets the kids ready for daycare and I write for an hour or so. When I’m working on something I feel good about, I will occasionally dip into it in the evening, but for the most part, I find it mitigates the writer guilt and the mom guilt to keep the book work to its allotted time slot. 

As an author who is an editor where most writers want to see their book or their work (Literary Hub), what did you imagine (dream!) for your book in the months leading up to publication? (This question is brought to you by this essay you wrote on validation, and I'm interested most in how you see the work of the book vs. what "success" means for it--rather than a "they like me, they really, really like me" vibe)

Before I sold the book, I was absolutely certain, despite the self-knowledge facilitated by both painful self-awareness and years of therapy, that selling a book would make me feel like a Successful Writer. A year after publication, with a shelf full of copies of My Real Book, I’m still waiting for that feeling to materialize! But the biggest surprise is that I’ve found that realization really liberating.

Because now I know, really know, that no amount of outside validation will make me feel any way but briefly elated. And that brief elation is lovely, no doubt.

But as I write my second book, the goal isn’t Feel like a worthwhile person. It’s Write the book. And that, I think, is a much less emotionally fraught position from which to write. 

I was inevitably disappointed with the ways in which the book was not recognized, but I do think I have come to realize that I was always going to fixate on the lists I didn’t make (unfortunately, working at Lit Hub, I see all the lists). The most unexpected joy of publishing the book has been, for me, the people I don’t know who have told me that it meant something to them. It’s not the public validation for which I still thirst, but as a person to whom books mean a great deal, it’s very, very special. 

You've written for a lot of HOT mags like Dirt, Romper, and Mother Tongue, if you could tell authors three (strategic?) points for pitching essays what would they be?

I am allergic to networking, which a terrible intolerance for a writer, but as both a person who pitches and a person who reads them, it really does help to leverage a connection, even if the connection is I read a thing you wrote and liked it, pay no attention to how I found your work email! (But definitely make sure it’s a work email, not a personal one.)

This is an obvious one, but do make sure you have a good handle on the tone of the site.

For all three of the publications you mentioned, I was writing, in some way, about grief over my mother’s Parkinson’s, but I made sure that the hook of the pitch was aligned with the ~vibe~ and interest of the site. It also helps to point to a recent piece you read and enjoyed there!

Finally, (specific) bragging is good! You don’t have to have a ton of publications, but you do have to convince an editor that you have an interesting point of view and the skill to follow through on your pitch. If you want to write about romance novels, it’s a huge asset if you have a massive nerdy spreadsheet of the ones you’ve read.

I would so much rather read a wonky essay about a very specific passion from an unpublished writer than a vague piece about why hard work pays off from a Pulitzer winner.

(NB to any Pulitzer writers I’ve edited, this was not a real example, I love you and congratulations on your well-deserved laurels.)

Bonus fourth question: It's so hard to write a funny novel, and The Glow uses humor in surprising and fun ways--is there a practice or prompt you recommend to get to the humor (funny bone, ba dum cha!), or is that simply the voice that came out of you for the book?

As a lapsed poet, I like to say that poetry and comedy are both, ultimately, about obsessive attention to language. A line of verse and a joke can both hinge on the placement of a comma. As a language obsessive, I really love working at that line level. I find plot really difficult (and have great admiration for those who do it well), but I will happily write a scene that is 90% jokey asides. My editor was incredibly helpful in getting me to actually make things happen, but I would always come back to the jokes. Books with zero humor really bum me out, I think because in the shittiest moments of my own life, I cling to humor the most.

Humor complicates pain in a way I find really interesting. For me, humor is not a deflection, but a way to live more deeply in the difficult. 

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Jessie Gaynor is the author of The Glow. Her work has appeared in Mother Tongue, McSweeney’s Internet Tendency, The New Yorker, TASTE, and elsewhere. She is a senior editor at Literary Hub and she has an MFA in poetry from the Iowa Writers’ Workshop, where she was a Rona Jaffe fellow. She lives in Richmond, Virginia with her family.