Twenty years ago Jenny Jackson wanted to write a novel. But she needed to make rent and felt wary of taking loans for an MFA course, so in her own words, she got a “writing-adjacent” job in book publishing. As an Executive Editor at Knopf, she championed authors like Gabrielle Zevin (Tomorrow and Tomorrow and Tomorrow) and Emily St. John Mandel (Station Eleven) before finally, mid-pandemic, starting to write a book herself. That book is The New York Times bestseller Pineapple Street, a zingy comedy about a rich family in Brooklyn. We shouted about it over a formica table at the booming Regency Café in Pimlico. 

The interview has been edited and condensed for clarity.

You’ve sidestepped a fry-up for scrambled eggs and a black coffee today. What is breakfast like at your place in Brooklyn?

Breakfast in our house is an unsustainable disaster, frankly. Every person in my house eats different things. So I get up at 4:30am and I write for a while and I caffeinate for a while and then my kids get up at 6:30am. Sawyer likes to have pancakes with mango or fruit on the side. He only likes carbs, but he'll make an allowance for fruit. My daughter Waverley went to see Jurassic Park Live not too long ago at Madison Square Garden where she bought a drink that came in a big plastic dinosaur cup. It's a Tyrannosaurus Rex head and the jaw lifts. So every morning she would like to be served coconut yoghurt with granola in the dinosaur head. And it's dishwasher safe, so we're like “All right, it's a giant pain but it's what she likes, so okay.” My husband eats all of his meals standing over the sink. He'll say “no, no, it's better for the crumbs.” So it's a bagel or something over the sink for him and then I eat toast at the table with the children.

My husband is really nice – he takes the kids to the bus stop so that I can continue languishing in my pyjamas for as long as possible. So I languish until about 9 o'clock and sometimes I'll continue writing. On a good day I'll go for a quick run to think about some more book stuff and then scribble down anything I have before starting my day. Inevitably in my first Zooms I'm wearing workout clothes, or I have a sweatshirt or sweater over my pyjamas. The early Zooms are not my most glamorous suits.

It’s the London Book Fair this week, and you’re here as both an author on a UK press tour, and an editor for Knopf [an imprint of Penguin Random House]. Are you doing editorial work between interviews?

Yes, I need to give editorial notes for the new Dolly Alderton book by Monday. It’s Thursday today. I’ll have the plane time on Friday and then on Saturday, Kevin Kwan, who wrote Crazy Rich Asians, is going to be in New York. I just gave him edits on his new book, and that’s our only chance to see each other. So it’s the flight on Friday and Kevin on Saturday, and if I want to see my children on Sunday I think I had better get to work on the train today [to Bath, where Jenny has a book event in the evening at Mr B's Emporium].

Having become a writer yourself and experienced the other side of publishing a book, will it change how you interact with the writers you work with at Knopf?

Yes, yes. There are two big things. First, I now have a totally different understanding of revision. When people didn’t like revision before, I sort of took it to be laziness. I now understand that when someone asks you to make strong structural changes, you are terrified that you're going to break your book. You are so afraid that once you pull on that string, you're going to unwind it. And so I misunderstood people's reluctance to edit in a fundamental way. And now that I do understand, it turns out I don't actually like revising, which is a bit humbling after 20 years of making other people do it.

And then I also used to have this attitude about prizes and the bestseller list. In general, I feel like prizes are just not indicative because prize committees are made up of humans, and every time somebody announces the National Book Award shortlist it's like — what did these five people love? So when the list comes out and you aren’t on it, I would feel sorry for the writer, but also, who cares what those five people thought? And then in terms of the bestseller list, I used to think, you know, what does it matter where you’re placing on the bestseller list when we’re looking at long term sales month after month?

But I get it now. I really get it now. Because these things are a mark to your peers that your book is working.

You joined Random House 20 years ago out of university, moved up the ranks, and you’re still there. Did you ever think about doing anything else? 

I feel like I probably could have worked in advertising and written copy and had some fun doing that. I love writing jacket copy. I love making something sellable. I love figuring it out. I think that writing compelling, original copy is the difference between a book working and not working. You'll notice how, in many reviews, people just repeat the descriptive copy, and the way that you frame the book for people influences the way that they read the book. I feel like in some ways, writing copy that sells is one of my favourite parts of the job, and it would have been possible for me to do that somewhere else.

When you started at Random House, could you imagine staying as long as you have?

Yes and no. Knopf is really wild in that it’s pretty normal to have editors stay for a very long time. It’s really common for us to be like ‘Oh, today’s a champagne toast for so-and-so celebrating 40 years here, or 50 years here.’

I mean, people don't leave. We joke sometimes that when you become an editor, it’s like you've been appointed to the Supreme Court and it's a lifetime appointment because people don't move on. And so when I started out at Vintage [the paperback arm of Knopf], I set these private goals for myself. I wanted to be a senior editor by the time I was 30, and I wanted to move to Knopf before I had children.

And in my head that was the plan and that so I guess in that sense yes, I always wanted to be here. At one point a part of me dreamed about being an editorial director or a publisher. That's actually not my dream. I think right now is my dream. I love working with my writers. And I think that once you become a publisher, you spend a lot more time thinking about budgets and thinking about strategy and what I want is to be in the weeds in the book with the writers.

At what point did you start thinking that you might want to be a writer?

Always. It was a dream that turned into another dream and then turned back again. I studied writing in high school and college. I wrote a lot in high school and college. And then when I graduated college, I just couldn’t figure out how to do it. I didn’t want to take out loans to get an MFA. I couldn’t figure out how I would ever pay them off if I did that. And so I was trying to think of a job that was writing-adjacent, and the hilarious thing is that I thought, I need to make money, I guess I’ll work in book publishing. I mean, great plan, right? But I felt like that was going to get me close to the centre of the action.

Then one of the very first things they tell you, and I'm sure you heard it when you started in book publishing too, is do not work in publishing if you want to be a writer. Because it’s always the bridesmaid, never the bride. You'll be resentful. Right? You definitely hear people say that.

People do say that. But there are also a lot of authors who start off working in book publishing.

That’s true, but I think when I heard that early on, I really believed it. That ambition was put aside for a long time.

I’m also someone who really soaks up the language of whoever I'm spending time with, which made writing myself more complicated. Like, do you remember when The Marvellous Mrs Maisel was a big thing, and everyone would just walk around Maisel-ing because there was something so infectious about that dialogue? Or sometimes if you’ve been watching a lot of The West Wing, you just go around being clever because there's something so irresistible about certain kinds of language? I find that when I'm reading a book, the voice really gets to me.

That helps me as an editor, but it's scary to think about being a writer when you're somebody who picks up other people's voices all the time. One of the things that was really hard for me when I did start writing is that I would have to take breaks, because an edit would be due and I'd be deep in the world of Pineapple Street and witty banter and, you know, rich people playing tennis, and then I would step out and be working on Cormac McCarthy’s The Passenger, or Peter Heller’s wilderness thrillers. And the language is so rich and incredible, but different. And so to rinse that off of your brain and get back to writing is a really hard thing.

What were some of the books you were reading for pleasure, early on, that made you feel like you wanted to write?

In high school I was reading Anne Tyler and Lorrie Moore. Those are the novels that I really absorbed. I have loved Bridget Jones’s Diary since 1997. That book opened up writing playfully, and writing humour in a new way for me. The Girls’ Guide to Hunting and Fishing by Melissa Banks was just so transformative. It made me want to get into publishing. I loved it so much.

Jenny Jackson

What are you reading now?

I am one of those people who always has three different books going at any moment. I have my bedside table book. I have my subway book. I have my living room book.

Right now I’m reading Big Swiss by Jen Beagin as my bedtime book, and it’s great, really wonderfully weird. I just started the new Curtis Sittenfeld [Romantic Comedy]. I recently read Breakfast at Tiffany’s by Truman Capote for the first time, which is ridiculous because Truman Capote lived at 70 Willow Street, kitty corner to where I was living. I’d read In Cold Blood in high school and loved it, but because I put a quote from Truman Capote on the front of Pineapple Street, I felt like a giant fraud for not having read Breakfast at Tiffany’s. It is actually quite a weird, dark book and not at all what I thought it was! 

What was it like for your colleagues, seeing you shift over to the other side?

I basically had two publishers. I've had the team at Pam Dorman and Viking. But then also, the whole Knopf team was out there pitching my book. All the publicists were pitching Knopf books and then also pitching Pineapple Street. We get these weekly round-ups of, you know, which books are on the bestseller list and which book has been featured somewhere and they kept putting my book on the Knopf round-up, too. It was wonderful. It's really sweet. It makes me feel weepy. 

What about for your writers, watching you become an author?

They have been so unbelievably generous. I had a book launch at Books Are Magic in Brooklyn and then a cocktail party afterwards in the neighbourhood. And Kevin Kwan flew in from Los Angeles, and Courtney Sullivan took the train for Boston. Chris Bohjalian drove down from Vermont. Jennifer Close took the train up from Washington D.C. So many of my writers came and showed up for me. They've been posting about it and writing about it and offering to help every step of the way. And it just feels like – how lucky am I? – because they're genuine friendships too. One of my authors read an early draft for me and gave me notes on Pineapple Street, which is a hilarious role reversal. It was my writer Lauren Fox, and she and I are just really, really close and she really wanted to read it and her notes were wonderful.

I remember when I first started out, some people would say don't become friends with your writers. It's like, they're your authors, they're not your friends, don't get too enmeshed because it gets messy with the business blah, blah, blah. But how can you not become friends? You love their work. You're talking on the phone, you're emailing. And then over time, it slips into, you know, sending each other funny texts. Lauren stayed with me when she was last in New York and you know, she was up late with my children playing games. You become friends!

Did any of your writers give you tips about finishing the book?

Rosie Walsh who wrote Ghosted [The Man Who Didn’t Call in the UK] said she likes to write in a white font, so that she can't see what she's writing and she won’t go back and edit. She'll just keep going. It’s a great tip but she's obviously a much better typist than I am. Because when I would turn it to black it'd be gibberish, and I’d be like, ‘Oh my god, I was off by a key the whole time.’

But I've been hearing a lot of writing advice now, and I'm starting to figure out what is applicable for me. There was a time I went to a writers talk and they were like, ‘Are you a Butt-in-Chair person or not?’ meaning, do you just make yourself do X number of hours every day?

I’m now a Butt-in-Chair person. One of my writers, Chris Bohjalian, he’s published 20-something books, and he told me that every novel has tried to kill itself at least once. And I definitely hit that point with Pineapple Street. Just because something is hard doesn’t mean it’s not going to work out, and just because you’re stuck doesn’t mean you should give up. That’s advice I wouldn’t have felt qualified to give until I got stuck and pushed past getting stuck.

How did you push past it?

By working, by trying things that didn’t work, by writing words that I then threw away, which sucks. Before writing myself, I didn’t realise quite how awful that is, to have wasted writing days. It feels terrible and it's not just because you’re wasting time. It’s because it feels like you’re wasting good creative energy.

Having had this experience with Pineapple Street, does it make you want to do it again?

Yes, definitely. After a good writing day, I become so insufferable. I call my husband, and I’m like ‘Honey, honey, honey – let me read you this part, let me read you this part.’ Because when you’ve written something good, it’s so fun.

Do you think you’ll stay in the world of Pineapple Street, or do something different?

I want to move away from rich people, because I think I’ve said what I have to say on the subject. I’m working on something set in my hometown, in Ipswich, Massachusetts. Ipswich is this magical place – a seaside town, three miles of white sand beach, a giant English Tudor-style castle overlooking the beach, where I worked as a teenager. I’m just dying to write something there. So that’s what’s next. I have some words. I just need to get my butt in the chair.

Interview by Jo Rodgers. 

Photographs by Liz Seabrook. 

Pineapple Street, Jenny Jackson's first novel, is available now. 

Jenny wears our Cropped Sleeve Linen Sweater.  

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