🟧 What makes a good newsletter?

A roundtable with five email critics: Delia Cai, Katy Waldman, Lily Meyer, Kyle, and Nate

Impressio Librorum (Book Printing), plate 4 from the Nova Reperta (New Inventions of Modern Times), c. 1580–1605, engraving by Theodoor Galle after a drawing by Jan van der Straet, c. 1550. Source.

New York Magazine may have collected dozens of ~media power players~ to discuss how unions are bad, but we here at One Thing have something else on our minds: the true future of journalism, email newsletters. There’s a lot of noise around the format; everyone is joining Substack or launching their own multi-platform solo creator brand. But there’s very little discourse or criticism about this type of content. It’s hard to find good newsletters and it’s hard to find good thinking specifically about newsletters: their writing, their editorial choices, their presentation. So we gathered some smart friends to fill in the gap and discuss the subject over email.

Kyle Chayka is a staff writer at The New Yorker and author of Filterworld; Nate Gallant is a writer and academic based in DC and one of the founders of One Thing; Delia Cai is a novelist and writer, author of Central Places and creator of the newsletter Deez Links; Lily Meyer is a critic, translator, and novelist, author of Short War; Katy Waldman is a literary critic and staff writer at The New Yorker.

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Kyle Chayka:

Email newsletters may be everywhere right now, but it's hard to define them. Some are from solo writers, others are produced by groups. Some have a single focus, others have no theme at all. What are the qualities you look for in a newsletter when you're deciding whether to sign up for it?

Nate Gallant:

I guess one thing I’ve really come to enjoy in a newsletter is a sense of thematic or conceptual specificity that feels particular to the more blog-adjacent areas of this world. Searching for a blog, at admittedly a very different time on the internet, seems in retrospect a little more about browsing diffuse online communities to find your personal niche. Now that algorithmic curation has ensured that our personal niches/identities are the main way we interact with the internet, I don’t find myself as excited by advertisements of expertise, personal brands, or culture/politics writing that competes with established outlets. I’m much more drawn in by a weird bit or gimmick that produces something new. I really enjoy high-concept formats or hyper-specific themes, which seem to afford the possibility that people can do something that is led more by an idea rather than the conventions of a format or imitating the way social media attracts attention.

In this sense, I think of “Dreaming in Japanese,” writer Leanne Ogasawara’s journey through The Tale of Genji. This is effectively a literary blog but organized around her reading of each chapter from Japan’s first long-form fictional narrative. I also really love The Sweeper, which is both a podcast and a newsletter on Patreon, and offers a very fun, geopolitically sensitive tour of far-flung stories from the world of soccer. They both give me the feeling of randomly finding a very well-done zine, with obvious differences and drawbacks in a digital format, but with the addition of being far more reproducible and accessible. But maybe I’m alone though in my search for a weird bit!

Delia Cai:

I'm afraid I have more utilitarian requirements than Nate's desire to find and fall down wondrous rabbitholes at the click of the subject line. I think that is because I'm just too oversubscribed to everything and yet I still think I can somehow scan everything that comes into my inbox (for mental illness reasons).

 As a result, I'm partial to newsletters that offer a distinct "service," whether it's alerting me to the top five Gen Z retail headlines or it's simply a reliable source of signal to be gathered, the better for trendspotting or even just figuring out if that one thing is worth reading. It's got to be snappy, too. I think the paid subscription model makes people think they should be penning long, discursive essays twice a week, or cramming a zine's worth of content into a single email. That's part of a whole other conversation about how much emails should "cost" and what they should provide in return. (The $50/year Substack norm feels so unsustainable in at least fifty ways!). But if your newsletter is regularly too long, I am already a little mad at you. 

Lily Meyer:

I am more like Delia than Nate! I treat newsletters as, well, treats — little breaks from my workday. So really, if it’s an essay, it’s just not what I want (with the exception of Haley Nahman’s Maybe Baby, which I am loyal to for millennial reasons). I also don’t trust any journalism that comes from one mind without colleagues or editors (an editor you pay isn’t the same, sorry!), so I don’t do analysis newsletters. What I *do* do is style and food, pretty much. Within those categories, I want good photos, good recipes (for food or outfits), and a good, sharp, developed voice. All three of those things are treats for me, and I’ll only pay for a newsletter that has them all. 

Katy Waldman:

I realized something while reading this roundtable discussion about newsletters! I am much more likely to approach newsletters as an extension of my social life than as an extension of my reading life. What I mean is that I don't really read newsletters for their own sake, or to find other things to read; I read them to stay connected to friends (both the writers of the newsletters and the people who read the newsletters). This approach is due to an idea that I'm clinging to in order to preserve my sanity, although it might be wrong: that high-quality writing is more likely to exist in books and edited journalism than in newsletters.

Lily sort of alluded to this already — her disclination for substacks that offer analysis — and it's why I'm less scrupulous than I might otherwise be about seeking out "wondrous rabbit holes," in Delia's great phrase. I want to stay connected to people I like; I want to know what they're thinking about; I want to give them my money; and newsletters can help with that. When the content is good, too, (which it often is), it's a nice bonus! But I'd still rather reframe newsletters as socializing because doing so relieves the pressure to be super-rigorous about subscriptions and how I'm spending my precious resources in the attention economy.

TLDR: It can be guilt-inducing to read a long Substack essay that doesn't go anywhere, but you don't have to have a brain-rewiring conversation every time you meet up with someone. 

Kyle Chayka:

I like Katy's thought about newsletters as socializing! Particularly as social media continues to disintegrate, we don't have as much of that ambient awareness of other people's thoughts as we might have had otherwise. I definitely rely on newsletters to bring me updates about what some individual is thinking about. That's why I'm so excited about Tina Brown's new Substack newsletter Fresh Hell and it's why I have enjoyed Alexandra Marshall's syndicated memoir An American Who Fled Paris. They're kind of like blogs with RSS feeds. But really the newsletters I open most often are information services: Magasin for fashion, Semafor Media for industry gossip, Delia's Deez Links for fun stuff online. They deliver consistently, which might be my best guideline for a worthwhile newsletter.

Another question I've been wondering about is, what is the role of "good writing" in a newsletter, or maybe more broadly, what is the role of “voice” in a newsletter? The newsletter form is different from the ~media institution~ as we've known it because newspapers or magazines tend to come with a certain unified tone and personality. I don't need my newsletters to be too polished, but at the same time, I want the creators to have some discipline... We often complain that writing is too blah and normal these days — are newsletters a space for weirder things to succeed? Or are they a new form of homogeneity, as newsletterer Emily Sundberg argued? To put the question another way, have newsletters succeeded in ushering in more interesting writing, are big publications embracing that change in any way?

Delia Cai:

Yes and no. I love reading Rob Horning, Blackbird Spyplane, Rusty Foster, Heather Havrilesky, and Sam Kriss in newsletter form often purely for the  demonstrations of sheer gymnastic prose, for example. But for the most part, I think the current Substack model of 1-2 posts/week drives most of us (and I definitely count myself as part of this) to push out the most harried, half-edited demi-thought ASAP in hopes of making readers feel like they're getting their money's worth, wordcount-wise. It's a looser, voicier writing more like what you'd encounter on Twitter or in blogland, but it's not always "interesting writing" per se. 

Sort of on this topic: one thing I've definitely noticed is how the standard for journalistic sourcing is definitely more casual in newsletters. You read an authoritative newsletterer saying "Oh, an insider told me this," or "I texted someone who worked on this closely," and it's very conspiratorial, very fun. You as the newsletter reader aren't really bothered to know more about who this source is. But that's probably not something you could slide by the fact-check desk at a big masthead. 

Lily Meyer:

I agree with Delia! I do enjoy that voiciness, though I’m picky about it, too. One newsletter that comes to mind is Subrina Heyink’s, which has this very confident tone that is precisely what I want in style writing (which hers is) but which you don’t get in, you know, Vogue. (I would like Vogue et al so much more if they bossed me around!)

I will say I really like a newsletter to be different from the rest of my media diet. I read newsletter book reviews if my friends wrote them, but I’m not seeking out more books stuff on Substack because it’s my real life, so to speak. Which is to say I don’t necessarily want big pubs reacting to newsletters, though I’m sure on some level they are. 

Katy Waldman:

I read my friends’ newsletters because mostly those are the ones I know about. (So hearing everyone's recs on this thread is great!) I’m also drawn to fun/smart aggregation (like Today in Tabs, Deez Links, and Garbage Day), niche content about topics I’m interested in (like Toonstack, a delightful stack by a group of cartoonists), and “the way we live now” acid trips (like Sam Kriss’s Numb at the Lodge). I try to stay on top of a few newsletters about books, craft, and literary gossip (Meghan O’Rourke just started one, and I appreciate Naomi Kanakia’s heretical takes and John Pistelli’s deep dives). But, on the whole, my approach is laughably haphazard. My inbox is full of substacks that I don’t remember subscribing to or vaguely remember subscribing to but don’t know why. Which ones am I paying for? Who can say?? Do you guys have this problem? You wake up to emails from a life coach in LA and an amateur jewelry maker and Freddie deBoer and wonder whether they somehow have your credit card information??

Kyle Chayka:

I turn to newsletters to get things I don't get elsewhere — a lot of lifestyle and consumerism stuff, honestly. FOUND NY, a newsletter launched by the former founder of Curbed, Eater, etc, collects real estate I definitely can't buy and hotels that I'm never going to stay at, but I enjoy it because it feels low-investment and fun, unlike other publications I read. I don't have to take it that seriously. But as Delia noted, that can be a problem when it comes to Doing Journalism, because newsletters are ultimately gossip sheets, Bridgerton-style. Like blogs, they aren't held to the same standard of credibility as a newspaper. I think that's mostly fine — though some newsy places sometimes get in trouble by reporting big, important stuff in newsletter form and maybe getting it wrong — but it does mean that newsletters aren't really going to save hardcore journalism.

Nate Gallant:

I really like the description of  “voiciness” that Delia and Lily picked up on, and despite my less utilitarian newsletter diet, feels like it could equally if not more accurately describe what I pretentiously insisted liking about “high concept” newsletters. I completely agree that it feels like a necessary part of the mostly editor-less chaos of the newsletter world. There’s something about the format of people writing half-way in between the hot hot heat of Twitter takes and the relative but restricted shade of being under a big masthead that seems to bring a feeling of personality, which I definitely enjoy, but as everyone has pointed out, is by necessity a little looser in feeling.

I think newsletters are “interesting” for me as writing because of that voiciness – the weird rabbit hole I’m after could be conceptual or inaccessibly frivolous (I agree about FOUND NY) but it is equally the ability to experience observant, funny, and creative people thinking out loud (which feels equally in conversation with the lower-fi, unscripted podcasting world). I guess this would be a bit more parasocial than in Katy’s thinking about newsletter’s being social, though? You sort of get to see people’s thought processes as much as their observations or conclusions because, as Delia also pointed out, the expectation is to put out a lot of text per week as a very small operation. And because it’s still not as raw as the immediate reactivity of social media but often built in the image of magazine writing, they can also feel “drafty”, though I wonder if that’s any different than “voice-y”?

Katy Waldman:

I want to respond to Kyle’s question about voice in newsletters and also to Nate’s point that the kinds of pleasures you get from newsletters, especially voice-y or personality-driven ones, might be more parasocial than social. I think that’s true! I really love Elif Batuman’s newsletter and we’ve never met. What I love about it is the quality of the insight coupled with a looser, slangier style, like when she wrote a whole post about “butthurt,” and it felt smart but also effortless, which made reading it feel effortless.

If I’m opening a newsletter, I’m probably burnt out or procrastinating. I don’t want to read anything that feels sweaty or needy or eager to convince me of anything! I don’t want the writer to be working hard. (Or if the writer is working hard, I don’t want to know about it—give me the relaxing illusion of conversational prose lol.) Obviously, newsletters are performances, but when the tone is intimate or diaristic enough, you can feel invisible—it’s like the writing is promising to turn a blind eye while you lounge in its shade for a moment. So maybe newsletters by people you know count as socializing (because you imagine they’re talking to you) and newsletters by people you don’t offer a kind of refreshing solitude (because you imagine they’re talking to themselves)?  

Kyle Chayka:

Here’s a concluding question: What do you want to see in newsletters into the future, the next year or two as the space matures? It could be a subject matter newsletters should cover more, a suggestion for a newsletter publication launch, or a style of writing you want to see more of.

I personally want newsletters to go in two directions at once, which should be doable for something that is more a medium than a genre. #1: I want to find more sources of great aggregation from voices I trust, newsletters that are superficial in terms of information but also broad in terms of scope. Leanluxe is a now-defunct weekly newsletter that was great at covering luxury consumerism culture and brand-building — it was a perfect mix of business and culture with great taste but far less pretentious than, say, T Magazine, and it had great imagery and visual formatting. I haven't found anything to replace it. (Please start a new or competing version!!! Feed Me from Emily Sundberg is similar-ish but less aesthetics.) #2: I want more depth in niche subjects. I haven't found a great coffee newsletter yet... I'd love one on ceramics, art and culture... I'd love a voicey art-world self-contained column... (Marion Maneker at Puck is kind of it). Basically I want a version of the Internet newsletter Garbage Day for everything I'm interested in. 

Lily Meyer:

I also would like more niche newsletters, especially about art! I like the newsletter format for mixing text and image. My dream would be for visual artists to start writing little sneak-peek-type newsletters that let readers snoop in their studios. (Why would they do this? I don't know.) In general, I would like more newsletters that offer the pleasures of snooping into a professional life I'm interested in. I don't want thoughts and feelings: I want a dog trainer's weekly report with photos and tricks. 

One newsletter I have appreciated for ages is 730 DC, which is an events newsletter with a sneaky and very useful local-politics element. It's hard to get local news in DC, as in many other places, and I rely on 730 and the DC Line, which aggregate it for readers who don't have the time to, let's say, read DC council minutes themselves. More newsletters doing this, please!

Delia Cai:

Is it totally philistine that I want......more images? Better images? Actual art direction? Graydon Carter's Air Mail was supposedly the luxury version of a newsletter, but there's just something so leveling (in a bad way?) about the text-centric newsletter format. Text alone does not ever feel glossy or premium! I'm not sure how this could be solved since most single-operator newsletter writers do not have art departments at their disposal (much less photo budgets), but I fear the Newsletterification of it all just means we increasingly end up down pages and pages of text with no visual reprieve. (Logos don't count). At least when The New Yorker makes you do that, you get (1) illustration every few thousand words!

Nate Gallant:

I agree with more + better visuals, for readability but because I could also use more like “curatorial” text for my insanely visual media-life. I share the frustration with the deluge of loosely organized text, and for me, simple and pointed commentary on art/design, on- or off-line, or just better pictures in bloggy writing could offer a more intelligible relationship for my overwhelmed brain between text/image: whether it's lo-fi architectural photography, pictures of dogs being walked, or just a well-placed dumb meme from 10 years ago. It would also be nice to see the platforms on which most newsletters run go beyond the basic, Squarespace-y modularity.

I'd also love to see more slice of life or culture writing in translation from less traditionally popular sites of media intrigue. I've enjoyed this about The Dial, which is, granted, more of an operation than a newsletter. Still, I could see individual writing offering something beyond than standard, news-driven menu of vacation vibes from millennial hotspots in Europe, reports from fashion/design hubs in East Asia/Scandinavia, or scenes of political catastrophe from the many fronts of post-colonial violence.

I wonder too if these things could be out there, and the means of newsletter aggregation are just not developed enough to sort by anything other than popularity, so it’s just all a bit buried at the moment…

Katy Waldman:

Art and photography — yes! Snooping into people’s professional lives — I’m here for it. Personally, I would love a newsletter with pictures of animals/weird animal facts. If someone’s dog “wrote” a newsletter, I would absolutely read that. This roundtable has also sold me on the value of a medium that encourages interesting people to weigh in on things that may seem lightweight or ephemeral: a passing trend, an episode of TV, that musician who was just in the news. Some texts seem to lend themselves to a perfectly newsletter-sized piece of analysis.

But I also want to suggest that maybe we should ban newsletters?? We are already drowning in content, and our time on earth is brief.

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