On the value of deadlines and editors

You’ve been a staff writer for a number of different places. How does changing a writing outlet shift the way you write, if it does at all? Each time you go to a different place, do you need to get used to a new format? Or, do you just keep doing what you do?

Let’s see. There was a hard break for me between the Village Voice and Deadspin. I was the music editor at Village Voice for about five years. Then I moved to Oakland, California, and I worked briefly for a company called Rhapsody. It was a streaming service, kind of like Spotify, that had been around before Spotify, but was crushed by Spotify in a very strange sort of tech world thing that I barely understood then and don’t understand at all now.

But, so, there was a brief period where I was half out of journalism. We were living in New York, and my wife was pregnant, and we knew for a fact that we didn’t want to raise kids there. The outlook for journalism, in general, seemed bleak, and I had conceived it at the time as maybe leaving writing for good. But shortly after starting at Rhapsody, I started doing some freelance work for Spin, which was still a print magazine then. Though in the middle of that, they stopped doing the print edition. It became online only. And I worked part-time there as an editor and a writer a little bit.

Coming to Deadspin, it was a completely different audience. You know, everywhere I’d worked previously up to, and especially at the Voice, it was definitely the same music-centric job, where the people I was working with and the people I was writing for, were very music-criticism-centric people. It was just more of an intense environment and when you wrote about Lana Del Rey, or whatever, you assumed that the person reading it had the full CV of Lana Del Rey. I cringe when I go back and I read some of these things now, just how referential they are. The in-jokes and the assumptions of knowledge that, looking at it now, all seemed to boil down the target audience to the 250 people who are also full-time music critics or thinking about music critics full time.

Deadspin is a sports publication. They had always done culture stuff, though, and they hired me as a culture editor to consolidate and coordinate all of that and fine tune it. I found, suddenly, that I’m writing about Grimes for an audience of people who—many of them—had never ever heard of Grimes. Certainly, they don’t have any preconceived notion of her or knowledge of her, and they don’t care about her necessarily at all.

It was an entirely different kind of writing for me, honestly. And kind of freeing. You know, I wrote the review of Lana Del Rey’s Born to Die for Spin and my mother-in-law read it. She was like, “I really liked that review you wrote of Lana Del Rey.” I was like, “Oh, thank you. Thank you very much. Yes, that was excellent.” She was like, “Yeah, I didn’t understand any of it. I didn’t really know who you were talking about, but it was really good.” And I was like, “Oh, shit.”

So, the big break that happened for me at Deadspin was that I had to better explain what I was talking about, and I had to justify caring about it as much as I did. I had to get across to a different audience, a more generalized audience, a much more skeptical audience. I think that was a big help to me. It was certainly jarring to realize that they did not care about Lily Allen as much as I did. I think it improved my writing a great deal to have to convey myself to people who weren’t necessarily obsessed with what I was writing about.

Then, I moved from Deadspin to The Ringer. The Ringer is a sports site, but also a culture site by design. The editors there are really smart and culture-obsessed people like I am. Amanda Dobbins was my editor for the first couple of years there. What was great about her is, she knew what I was writing about, but she didn’t care about it at all. She didn’t like it, you know? And so, my audience is a little more generalized, again, and it’s not a hardcore-rock-critic audience like it seemed like the Voice was at the time, but even my editor, or the first person reading me, is coming at it with a little bit of skepticism, has to be convinced that this subject is worth my writing about it.

That was a very helpful thing to me, as well. It made me work harder and it hopefully helped me from falling back onto the lazy sort of in-jokes that, when I look back at my old work, seemed to just totally infect my old work.

So, some jumps between publications are bigger than others, but it can be a really seismic shift in the way you have to think and write. And it can make you better.

I freelanced for a long time, as well, and it’s definitely interesting to be faced with different audiences and editors and processes. One other thing I found for myself is that when I had a kid and then a second kid, I had much less time, and that also shifted the way I wrote. Now, I’ve almost been forced into minimalism—in my opinion, it doesn’t make the writing less interesting. I just don’t have all the time in the world to work in a reference to Ulysses, you know?

Yeah. When I was at the Voice and I was writing a column that led the print music section—that’s a full page and about 1,000 words—I would usually write it on Sunday night. It would take almost exactly three to four hours every time. I got locked into that. I think about my life before kids and the whole thing seems like an absurd indulgence. I don’t have any idea what I was doing with my time other than knowing that I was wasting the vast majority of it.

I’ve been really privileged to have these jobs as full-time jobs and to be able to treat them as 9:00 to 6:00 enterprises. You know, I’m just living here in Ohio, in the suburbs in Ohio, and just working out of an office in my house that crucially has a door. And so, I don’t have any kind of commute. I don’t have any sort of WeWork situation, but there’s just enough of a divide between work and not work where I can sort of treat this as a 9:00 to 6:00 job.

The reality is, I benefit hugely from being able to be with my kids anytime during the day if they need it, or driving to school—it’s a fluid sort of porous thing that’s great. But it has just enough of the structure of the 9:00 to 6:00 where it still kind of feels like the way that I used to write. I have an idea of how many hours it takes me to write X words, and that’s changed over time, but there’s enough of a structure, a through-line there, that it’s not been that jarring of a change.

Do you find that because you’ve been writing for so many publications for so long, and you do work all the time with deadlines, that you don’t have time for outside writing projects?

The answer to that is that I’ve been working on a novel off and on for, oh god, it’s getting up to five years now. I’ve written a few drafts and shown it to a few agents and not had any bites yet. That was a completely different feel. I wrote it exclusively at night after the kids went to bed. I don’t know if I deliberately decided to compartmentalize it like that or it just happened naturally, but starting with Deadspin, again, I have the 9:00 to 6:00 structure, and get off of work, and have dinner, and chill with the kids, and put the kids to bed. And then, that three to four hour block until I went to bed was devoted to the novel. That went on for several years, and that’s still going on, though it’s sort of spaced out at the moment. But that’s the first time that I’ve had a second project of any scale going other than my day job.

I didn’t deliberately set out to separate them as starkly as I did, but in the few instances when nothing was going on in my day job and I had this block of two hours, and it’s like, “Oh, I can work on the novel,” it just didn’t work for some reason because the sun was up. I don’t know what it was, but I created this psychological division that worked for me. Even if I had an opportunity to put a little more time into it, it just didn’t feel right.

I get up early, at 5am, to do my outside writing. I remember when I interviewed Zach Baron for TCI, he was saying that he can only write before noon. After noon, he has nothing left. Are you able to write your stuff for The Ringer throughout the day?

Even with kids, even with obviously getting up early with them, I am still not a morning person. And so, if anything, again, the novel was written almost exclusively from 7:00 to midnight or 7:00 to 2:00 AM or whatever. I don’t particularly write well in the morning. As far as the day job goes, some days I’m writing steadily the entire time. Some days it’s sort of half and half. But in terms of creative writing, in terms of the novel, yeah, it was entirely at night for me. I still prefer nights to work if I can. The block from 9:00 to 6:00 is just devoted to whatever the day job needs that day. And if that’s writing, that’s fine.

I like the romantic ideal of the hours from 5am to 8am being my time. My wife writes romance novels, and that’s what she prefers. You know, she would vastly prefer to write in the morning than to write at night. But I’ve never been like that. I wish I could be like that, but I apparently can’t.

Do you have any tendencies you need to work against with your writing?

I find myself repeating and just overusing adverbs. And there’s certainly been plenty of times when I’ve thought of a joke and then something in the back of my head says to Google me making that same joke in a thing I wrote four years ago, or whatever, that’s happened enough times that… yeah. I hope, at least from my perspective, that I never fall into a rut, but there’s definitely a pattern that you get into.

Part of what I do at The Ringer, a big part unfortunately, is obituaries. When figures of a certain age die, there’s a certain quadrant of that site that is populated by people who were alive when that figure was first a big deal. Here explicitly, to speak to that historical context, is a big part of what I do. And the structure of that is interesting. If you want to start with some sort of personal anecdote for you, related to that person, or you want to focus in on one song, it’s never quite hardened into a template like that… But yeah, if you write enough record reviews, if you write enough obituaries, if you write enough 20-minute artist profiles, inevitably there’s a pattern they get set in. And it’s the challenge of working within that without it ever feeling overtly like a pattern to you, or to the person reading it.

Have you ever handed in a piece that you thought wasn’t successful?

When I go back and read things, I like some things that I’ve written more than others. I don’t know if there’s one specific thing that I would point to as a failure. It’s just sometimes you go on these big reported things and you’re not able to interview the people that you’d like to interview. Like, I just wrote a big thing about the first Coachella music festival in 1999, and I really hoped to talk to Paul Tollett who’s the founder of Coachella and now the CEO of Goldenvoice, which runs Coachella and all that. I talked to a lot of artists who played it, but I was hoping to talk to him, as well, and I couldn’t, and that does change the piece. So on that level, yeah. There have been times when I’ve done a reported piece and I’ve not been able to talk to as many principals as I would like.

When you’re writing three or four things a week of varying sizes—sometimes I’ll completely forget that I’ve done something and go back and look at it and be like, “Oh man, this is really wordy and incomprehensible.” And sometimes I’ll read it be like, “Well, that was all right.” But there’s nothing that feels, in my memory, like a total failure in the moment or in retrospect. But you know, there is kind of a sliding scale between forgetting about it and then cringing upon rediscovering it.

Because you do write so often and so much, you have to keep going. If you wake up on a certain day and you don’t have it in you, are there any tricks you’ve come up with that get you through that creative block?

I just sort of walk around my neighborhood listening to music a lot. I live in the suburbs, so I just walk around the sidewalks and around the various parks in this area. Exercise like that, I find helps a lot. And there’s always kids stuff dotted throughout the day, whether that’s driving them to school, or driving them to sports, or just stopping work for a little bit to play with them, since they are home here in the house when they’re not at school. There’s enough of those little breaks. There’s always something I can go and do for an hour or 15 minutes, at least, that does kind of break that cycle.

When I’m writing a piece, if I get blocked in a micro way for longer than 30 seconds, I just reread everything that I’ve written up to that point, which is why I end up reading the first paragraph 50 times over the course of writing it. It’s just sort of a weird subconscious reset where I just read the whole thing again and then eventually I’m able to move forward.

How do you edit your own work? When you hand something to an editor, what have you done up to that point? What’s the process for you getting a draft done and ready for another set of eyes?

It’s all working through Google Docs. I guess I’m more of a “veteran” writer. A lot of The Ringer staffers are young and for many of them, this is their first writing job. And so, part of what I hope that I’m bringing is, I’m trying to be as low-maintenance as possible, just not needing a whole lot of prodding in terms of meeting deadlines and logistical stuff like that, but also, just filing as clean as I can. You know, trying to include the YouTube links, and the art links, and stuff like that, and just trying to make it as clean and as simple a process for my editor as possible.

Like I said, Amanda was my editor for the first couple of years at The Ringer, and she was awesome, both because of her skepticism of the thing I was writing about—which I think really helped hone what I was writing—but also just the suggestions she had and the way that she would shape things, and the way that she would identify, as you say, those sort of ticks and repetitions that come out. And she just really improved my work a lot. The guy I’m working with now, Justin Sayles, is the same way.

I definitely want to be edited on some level. I definitely want some sort of pushback. If it’s getting too wordy or just too incomprehensible, I really need that feedback. But I am vying to make things as simple as possible and not require a great deal of back and forth.

If I’m writing a larger thing with a ton of interviews, and it’s 5,000 words or whatever, then there’s a few different drafts of that and more macro changes. But if you’re talking about a simple piece in the 1000, 1500-word range that I wrote in a day and might even be going up that same day, I’m hoping that my editor comes back with a few changes or suggestions and maybe there’s a few things that I add, but that it’s not a terribly long process. I’m trying to make it as streamlined as possible.

There was this thing on social media a little while ago where people were complaining about editors. They were, I think, offended by having to be edited. Personally, I enjoy the editing process. It makes the writing better and I don’t take offense to it. Even if you disagree with the editor, or get an editor that isn’t the best, I’m bound to find something useful in that exchange. I’ve never had an edit be a completely worthless situation.

I haven’t either. I think across the board, certainly at The Ringer, but I think everywhere I’ve worked, every edit that I’ve gotten has improved the piece. I think it’s crucial to have somebody look at it who’s not as biased as I am, having written it.

To work at The Ringer, a place that has a tiered structure of editors, and also copy editors, and also fact checkers, is an unimaginable luxury, unfortunately, in 2019. A lot of people came up blogging first for themselves, and didn’t have that kind, or any kind, of editing structure. You know, if you’re typing directly into the CMS, and the thing that you’re writing is going directly onto the internet with no intermediary whatsoever, then I imagine it would be really jarring, a couple of jobs down the line, to suddenly have an editing process at all.

Coming up as I did, with alt weeklies, there was an arts editor and there was an editor above the arts editor who would often read it as well. I always had that kind of process. As my career went on and just looking at these other publications, that already seems pretty drastically different. And so I can imagine new writers would react to editing much differently.

Have you ever missed a deadline?

Yes. I’m trying to think… I feel like I’ve been pretty good about it at The Ringer. There’s been a few instances where I’ve asked for an extra day, a day before something was due. There’ve been a few instances where I’ve asked to modify the deadline, but I don’t think there’s been an instance of something that’s been due that day, and at the end of the day, I’m like, “It’s not coming.”

You were saying how, as a veteran writer, you attempt to not take up a huge amount of space as far as the resources of the editor, or try to file things on time, and with all the links, and all that. What kind of advice would you give to someone just starting out—or someone wanting to figure out why they keep getting fired?

I think it’s understood when you’re young that it’s going to be a struggle at first. Other than the diligence of just doing the work, and keeping to those deadlines, and doing what you said you would do, I think it’s not fun to be edited on some core intrinsic level of feeling like, “This beautiful thing that I wrote is not perfect?” “Who are you to tell me that my work isn’t perfect?” That sort of animal instinct that you have? The sooner you can learn to set it aside and the sooner you can realize that almost every piece, anywhere by anybody, is improved by another or several other sets of eyes on it… The sooner you can submit to that and realize that your work is going to be better if you are edited, if you do get a certain amount of pushback, if you are called on your clichés, if you are called on your repetitions, then your work will be better. And, the sooner you can learn that, the better.