Writerland, Chapter 30: Please Be My Editor, Rachel Dry. Please.

Writerland is a newsletter from The Delacorte Review whose mission is to help writers tell the stories they need to tell.

The relationship between writers and editors is much like the relationship between teenagers and their parents. The kids are desperate to assert their independence even as they need to know their parents are there, when needed, at any time - day or night - for any reason - small or large - even though when it comes to writers and teenagers there are never small reasons, not when everything matters and if it doesn’t get fixed immediately you could, like, die or worse still, have the best sentence you have ever written cut.

If you are a writer, you know I am speaking the truth -- I have been that writer, and am still that writer -- and if you are an editor you are nodding your head like a maddeningly wise parent, thinking, the poor dear, thinking he or she could do this on their own. To you editors I would offer a cautionary note: you can mess this up. A show of hands please from everyone whose parents always got it right when they were sixteen. Thought so. 

Every writer I know and admire longs for an editor she or he can trust, the editor who can make you better. The editor for whom -- and I have heard this said more than once -- they would run through walls. There are writers who believe they do not need editors, who resist any editing at all. Some of them are talented. But I have come to believe that skilled as they are, their insistence on going it alone stunts them as writers, and too often that means that despite their A+ aspirations they will never get better than B+ or A-.

Writers need editors, but not just any editor. I have had bad editors and terrific editors, among them my colleagues at the Review, Mike Hoyt and Cissi Falligant. That I have done my best work for the best editors is not accidental. I wanted to please them but I was not afraid of disappointing them. Tricky for an editor, like a parent, to pull that off. 

Which explains why there are editors whose names get around, whom writers hear about from other writers and who, when they get the chance, will leap to work with them. One of them is Rachel Dry.

Rachel is an editor at The New York Times, and before that at the Washington Post. Her current gig is as Sunday Business Editor. Before that she was deputy politics editor for enterprise, deputy op-ed and Sunday Review editor. At the Post, she was, among other roles, the features editor in Style and the deputy Outlook editor. When I mentioned her name to a Post writer who once worked for her, she sounded so wistful you might have thought she’d been abandoned. 

Rachel is very smart and very funny; she also does stand-up comedy. But brains and wit alone do not explain what makes her an editor whom writers love to work with. So I asked one of those writers, Matt Flegenheimer, what made her so good.

He wrote: A field guide to being edited by Rachel Dry: She will have ideas. Better ideas than your ideas. Until, one day, your ideas also start sounding better than your ideas. She will let you take credit for this. She will tell you when you’re wrong. She will tell you when she’s wrong. She will stay up all night with you when the president’s coronavirus diagnosis lands at 1 a.m. and you decide you have a riff that can’t wait until morning. She will hold only productive, conspiratorial grudges against shared antagonists. She will inspire a loyalty fierce enough that her reporters will insist on showing up to a Des Moines open-mic night to watch her tell (killer) jokes about Vermont to befuddled Midwesterners. She will know when to let you cook on deadline and when to nudge you toward better ingredients. She will ask, in your first real conversation as editor and reporter, “What is your worst-case scenario for us?” She will not roll her eyes at the answer — producing perfectly fine, forgettable enterprise — and then she will not let it happen. She will call you out for using hacky devices like the second person. You will be very lucky.”

But how does she do this? How does any editor become that editor? I put the question to Rachel. What mistakes did she make? If you want to be that kind of editor, pull up a chair, as the great baseball broadcaster Vin Scully used to say.

“It’s important to fully understand that it’s the writer’s name on the story, not yours. Most mistakes, I have found, come from a misunderstanding in that territory,” she wrote. “That can take a few forms, but usually it means pushing too hard for something you want that is just as good as what the writer wants. (This holds true even if your idea is slightly better, but only slightly.) It’s her name. It’s his Twitter handle, and carefully cultivated and maintained public persona that will do battle online, if battle is to be done.

“Another mistake I seem doomed to repeat is being an unreliable and often slow emailer. This is not a good quality when working with anyone, but especially writers. You want their creativity focused on the work, not on imagining just how it happened that you were attacked by a bear on the way home from the subway -- they’re very sad but of course they’ll give a beautiful and moving speech at your memorial service – because that must be the reason you haven’t written back.”

But what, I asked, do writers need from editors?

“Writers need kindling and a firepit and an editor who might question the use of this metaphor from someone (me) who has just recently developed some modest skill in fire building.

“But, committing to the bit, what I mean is: Even, or especially, some of the most creative reporters and storytellers might find themselves stalled out when staring at a blank story list and casting their gaze over the entirety of the human condition for something to write about.

“Creativity often needs constraint to really take off. So what I offer is a voracious eye and story-generating mind. In the best collaborative cases, I present a pile of kindling culled from the news cycle or the season or something I read or questions that have occurred to me while on a walk. And together we figure out what to toss and what to ignite.

“Writers also need some guardrails, the contained burn of a firepit. So once the flames are going, they need the safety of someone saying: actually, that is enough, that joke is a bit much, this person’s name is not necessary, this scene is just to prove you went to that place not for any other reason, I approved your expenses and know you drove there but really we should cut it – oh and your real nut graf is the kicker, sorry. Now we’re cooking.”

So then, I asked, what did you have to learn to succeed as an editor? Here she invoked her standup life. Not that it’s a requirement for editors, mind you. But humor helps. Just like with teenagers, lest you lose your mind.

“I learned to tell jokes onstage in bar basements in Washington DC. That might seem like a circuitous way to hone one’s skill in newspapering. But it worked for me, not just because ritual humiliation is character building. As I developed a standup act and had a clear outlet for my own voice, I was able to get out of the way of reporters more easily. I was better able to elevate their voice and the way they wanted to tell a story, not jam my own ideas on top of theirs. 

“Open mics with strict time limits, bar shows with easily distracted crowds, the way a few seconds can stretch into eternity when an audience is totally silent – those were also always very good reminders that keeping people’s attention is extremely difficult and it’s often better to be concise.

“I learned that editors are fundamentally salespeople, which is not a bad thing to know and acknowledge. Framing a story properly, writing a headline, social copy, pitching a story in a meeting full of people who generally hate everything (newspaper editors) and getting their attention—those are all sales skills, and, working backward, knowing how to sell something usually means knowing how to make it compelling in the first place.

“Finally, I learned to know when it’s worth making someone climb the stairs: I once commissioned an essay from Carl Reiner. His longtime assistant was our go-between, and we had a few slight misunderstandings on the edit. We were almost done and ready to publish when I called to ask about one final change. If memory serves, she said something like: “Mr. Reiner’s office is up the stairs. I am not walking upstairs to bother him about that.

“She was right.”

We’ll be back in June to talk about what a writer friend calls “engineering” a writing life. Because, after all, very few of us get to write all the time, unless we are Stephen King or Danielle Steel. For everyone else the trick is finding ways to make time to write, and still pay the bills. 

And if you’re looking for reading material over the holiday weekend (or any weekday or weekend, for that matter) check out Issue #6 of the Review -- Hope and Loss -- which is now available in print. Until then, stay safe and well. 

Nothing good ever came from writers punishing themselves. We know writing is hard. We’re here to show that it doesn’t have to be torture. The Delacorte Review Newsletter comes out every other week. Subscribe to get full access to the newsletter and website. Never miss an update.