Kyle Chayka of The New Yorker on Newsletters, Feature Writing and Media

On November 22, 2021, Study Hall held an AMA with Study Hall co-founder Kyle Chayka about online communities, subscription-based newsletters, and the broader media industry.

On November 22, 2021, Study Hall held an AMA with Study Hall co-founder Kyle Chayka about online communities, subscription-based newsletters, and the broader media industry. Kyle runs Dirt, a daily newsletter about online entertainment, and is a contributing writer at The New Yorker, where he covers technology and internet culture. Here’s a condensed version of the AMA, which has been lightly edited into Q&A format.

Why did you start Study Hall and what led you to move to a newsletter-based subscription service? 

P.E. and I started Study Hall because we were both freelance writers and felt there was no support network or centralized resources for freelancers in media, and sites like Vice, BuzzFeed, and Vox Media were all relying so heavily on freelance contributors. No one really knew the scope of the market or what rates were being paid, so we actually started as a coworking space because we needed office space, and moved into paid digital subscriptions for media-industry news and opportunity lists.

We were early in the move to paid digital subscriptions, but we did it from the beginning because we wanted to be sure to have the money to pay for any work that needed to be done, rather than relying on free contributions from anyone. I’ve also always felt there was a lot of power in maintaining our own email lists and having a direct route to our readers, which I think comes from being a freelancer — people never know where to find your writing.

 

At this point you have created several inroads to accessing your work (written or otherwise). I’m thinking about your personal website, as well as the several newsletters you run or contribute to, but specifically your Kyle Chayka Industries newsletter, where you gather your writing projects in one place and provide BTS content. 

Yes. On one level I like starting new projects for myself, and on another I never had the right spaces to pitch every story I wanted to write. So now I have a whole range of spaces for stuff I want to do. Right now, my main job is writing a column for the New Yorker website on digital culture and platforms. But I started Dirt to talk about very random, small ideas about streaming, TikTok accounts, fun multimedia online, and whatever else. That has a life of its own now, edited by Daisy Alioto and featuring work from many freelance contributors. Otherwise, if I have an essay that doesn’t fit in the New Yorker, I’ll put it in my personal newsletter, which I think really connects with people who are truly SUPER interested in what I specifically do.

 

When we spoke with P.E. Moskowitz last week, a number of people asked about using their newsletter as a space to keep the unused bits of reporting or research. So it seems like you have no qualms with moving your work into a newsletter space, even if it’s an unpaid newsletter?

Yeah exactly. I think as long as it reaches readers, it’s good. But that also has to do with my personal writing career, because any mode of advertising myself and putting out work could benefit the sales of my book, who pays attention to my writing, etc. Even though the newsletter is unpaid, it’s kind of “monetized” as a marketing tool. I also like it as a very last-ditch insurance policy for making money: If nothing else was happening, I’d turn on paid Substack subscriptions.

 

What have been some successful methods for structuring your longform work (5,000+ words)? I feel like those stories can get thematically unruly and I wanted to hear how you tackle those. 

I am obsessed with structuring features and long essays. My one trick that I do every single time is I mark and label the section breaks. So I’ll write an outline that’s like:

1. Anecdotal Lead
2. Who is this person / Why do we care?
3. Scene with them in action
4. End scene / writer commentary

I write into that outline, making sure every bit under each section follows the theme of that section. My writing tends to be more thematic than narrative, but that structure can also work for narrative — marking out a specific chronology or moments in a travelogue, or whatever. So I ruthlessly follow the sections I set out, and create a new section if I see a new theme emerging.

But also generally if you are writing for a magazine, they already have a template for how features work. Every NYT Mag profile is structured basically the same way, and every New Yorker story starts: 1. Lead / X happened on Y Date 2. History of X subject.

For my book writing, I had to figure out how to extend 5k words to 10-15k words, which was really hard and I basically did it by breaking that up into 2k-word sections that built up to 15k-word chapters.

 

What I’m seeing in your answer is that you use structure to strengthen the narrative elements. Do you have a similarly structured research and reporting process?

I tend to do as much research and reporting as possible before I start writing, so I have a cache of a dozen interviews and other research, which I’ve highlighted for interesting parts, and then I write the outline, and I follow that. But my reporting — especially for non-travel stories — tends to be very haphazard, like I’ll basically call as many people as possible and figure out what brings them together. I also suggest figuring out the thesis / idea of every story, and being very ruthless in cutting stuff that doesn’t adhere to that central thesis.

 

I’m super curious about how you manage all the information around technology, specifically trending and controversial technology like NFTs. One of the things I appreciate about your writing on online culture is that you stick to narrative and structure, giving lay people a chance to understand what’s going on. But I also see a lot of tech writers just regurgitating information or somehow making it even more abstract.  

I tend not to get into nuts and bolts too often, which is sometimes a bad thing. I don’t tend to break news or details about companies. But my writing usually follows an idea or a feeling that I hope other people will identify with. So the technical stuff, or the very niche stuff, usually stems from something that’s recognizable to people. My new essay on digital nostalgia and pixel art goes into weird NFT stuff, but it emerges from a sense that the internet now sucks and it was better to play Pokémon in 1999, which I think people will identify with. So I try to focus on ideas, narrative, and characters rather than tech. That works the same for business stories, as well.

 

Another part of my curiosity stems from your willingness to investigate these trends and build a brand (maybe even several brands?) around them. From the outside, it seems like your work in digital publishing informs your writing about digital culture at large.

Yeah, I don’t think I can separate my interests that well. It all tends to flow together and I think often the best writing comes from a place of some experience or familiarity, so maybe I’m a better writer on media and platform dynamics because I’ve had to contend with them myself. I’m very familiar with the pressures that digital platforms exert on creativity, so I have been interested in writing about them.

As far as a brand, I think freelance writers especially benefit from being known for covering one or a few subjects. I never really decided what “brand” to have, I just kept writing about the stuff I was most interested in and those subjects reinforced themselves.

 

Can you walk us through your writing career, and also talk about how you found your thing, your niche?

Yes! Basically, I had staff jobs in art media from 2010-2012, then I wanted to branch out more and began covering technology and business stuff as a freelancer. I freelanced kind of all over until I settled more into book and magazine writing in 2018-2020, then I started as a contributing writer at the New Yorker this year.

 

Any tips or strategies on negotiating rates for freelance work? Are those strategies any different for contract or longer-term ‘contributing writer’ roles?

I’m not the best negotiator ever, but I think the trick is to always ask for more money and never be embarrassed about it. Longer-term gigs should pay more than one-offs by whatever basis because they’re more of a commitment for you. Always try to find out what other people are getting paid at the same place, especially for contract gigs. That can be tough and varies a lot.

I just wrote about what I was most interested in or what assignments editors gave me, which became more frequent over time. At the top it was maybe 50% assigned stories and 50% pitched stories. Now I pitch all of my New Yorker columns. I think my personal niche just comes from my ideas about digital culture and how algorithms influence our cultural habits, which is very niche. It’s also what I found resonated with people most, and is what drove my most popular pieces.

 

Have you always written longform?

I began writing longform more around 2015-2016. I wanted to write “features” but I didn’t really know what that meant, and I ended up doing more profiles and essays. So I evolved into longform over time. I will put one of my golden rules here: Editors will always ask you to do more of the work you’re already doing, so if you want to do longform, you should publish longform. If you want to write about true crime, publish true crime. And you should publish what you want to write, no matter where it shows up or how “prestige” the outlet seems. It’s better to publish a story that you really wanted to do in an indie magazine or on a random website than a story you don’t care about in NYT Mag, money notwithstanding.

 

I think that speaks to some of the anxiety we see about bylines, newsletters, branding, etc. It seems like people think there is a lot more strategy that goes into it when what you’re saying is, “Write about what interests you and let that interest build an audience.” An organic approach from the algorithm guy?

Yeah, for sure. I am definitely privileged in that regard, but I cared less about where a piece was showing up after I collected a lot of bylines. It was more about what an editor allowed me to do, and how creative or interesting I could be. I don’t think there’s one model for everyone, but as far as developing a reputation as a niche essay / feature / magazine writer, it’s definitely about pursuing what interests you most and what results in the most impressive product — the thing that drags readers in. What’s great about online  publishing now is that if a good feature shows up anywhere, Twitter will direct people to it. Doesn’t matter if it was published in The Drift or The New York Times or on someone’s Substack. And everyone is always looking for The Next Big Voice in whatever field, so novelty counts for something.

 

Are there any good features or feature writers that you would point people towards as an example of a niche, compelling product?

Rachel Monroe is an amazing true crime writer, who is deeply interested in the ethics and philosophy of the genre — kind of meta-true crime, as her book addresses. Gideon Lewis-Kraus is one of my favorite writers for incredibly knotty conceptual features, which often have some kind of structural or literary gimmick. (Both are at the New Yorker now also lol sorry).

I don’t think you need to choose which “genre” of writer you are, but sooner or later people will identify you with something. Gideon Lewis-Kraus came from Harper’s and NYT Mag and kind of the rarefied literary sphere, so he already had his bona fides.

 

Can you talk a bit more about how you develop and sequence a story’s structure? How do you work with editors during that process?

That really depends on the subject. I think I have a sense now of how narrative works for me, which is often the narrative of an idea, and expanding and shifting the angle of something. Generally, I think sections should work in terms of themes or scenes, or both. Perhaps it’s one character, or one conflict, or one philosophical debate per section. Developing your sense of how each section should both be different and a development on the last one comes with time and experience.

I tend to work mostly on my own when writing a story, and make the structure on my own. Sometimes an editor will want to change that, which is totally fine, but that will be after the first draft goes in. When a story is ambiguous, I like to talk through it with my editor before I start writing, which is a habit I should cultivate more because it helps to be on the same page. I don’t think “structure” is some magic bullet though; structure follows content. Having a structure be too predetermined can be bad. I think John McPhee has caused some problems in that regard.

 

I’m curious to hear what you think will be some of the 2022 media trends.

More people are going to jump into crypto and NFTs — NYT is hiring a crypto reporter right now. I think more coverage is desperately needed and few people take it seriously. I think we’ll see more individual newsletters and more consolidation of voicey writers in big publications, mainly the New Yorker, The Atlantic, NYT. NYT will get bigger than ever and will be increasingly targeted for its missteps and opacity as an institution. Writers will also start going straight to TikTok video essays instead of writing.

 

Would you mind giving a brief overview of how the whole book proposal process went for you? Where’d you start, how’d you figure it all out, land an agent, sell it, etc? I know you have a new one in the works, but I’m specifically curious about how you sold your first. 

Big questions! Agents contacted me because of my writing and bylines, which was happening a lot circa 2014-2015 in NYC. I signed with an agent (who I love) before I had a solid, single idea for a book, which is not something I would totally recommend. Don’t get an agent until you have a very clear book idea or need to negotiate some kind of creative deal. As I was writing this NYT Mag First Words column about “minimalism”, I realized that there was enough material in the minimalism discussion to fuel an actual book, which is a rare quality in a magazine story idea. So I developed a proposal out of that, working closely with my agent. It took a very long time, and it didn’t sell on the first round out. I got good feedback, re-edited the proposal, and then it sold. No one should want to write a book just to write a book, it’s too hard. You’ll know when you have something that has to be a book.

 

During the actual process of selling the proposal, did your agent provide any guidance that changed how you saw or valued your work?

For better or worse, everything in nonfiction is memoir now, or if it’s not memoir it’s investigative hot-button politics / society / crime stuff. My agent essentially acted as my editor when writing the proposal, so her feedback influenced every part of it. The selling part was totally out of my hands, and I didn’t want to know any details of it.

 

Is there any particular advice you’d give for less established writers who are interested in getting into freelancing, pitching, and publishing?

Probably something like what I said above. Definitely pitch and publish the stuff you want to write, no matter where it’s showing up. Start with any publication you might have an inroad to, and try to figure out what area you’re interested in, like there are various types of freelance writers and journalists. Are you into essays? Criticism? Crime? Business? Tech? If you don’t know, try all of it and figure it out.

 

What about building a community while working as a freelancer? It feels like being involved in Study Hall and similar community-focused projects didn’t hurt!

Yeah, for sure. It always helped to feel like I wasn’t alone in struggling to publish, be creative, and make money. I think community can mean a lot of things, but what it comes down to is having people to share information with and complain to, discuss how things are going, debate if ideas are good or not. Also, many people — freelance and not — have shadow editors or friends helping them develop their work, so those are good relationships to form. I’m a big fan of starting your own thing if what you want doesn’t already exist. Everyone in media is always jealous of new, cool stuff. It’s also a really boring and moribund time in publications! Good time to start over

 

If anyone has any follow-up questions, you can reach out to Kyle at [email protected].

 

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