• Sophie Poole

Posting Into the Void

Updated: Mar 3

You, me, and everyone else’s Substack newsletters.

By Sophie Poole


Newsletters distributed in early modern England related the “diverse particulars” from European outposts to English readers. Corantos, meaning both a French running dance and a newsletter, slipped through the inky hands of the literate and landed gentry. Proto-reporters called intelligencers emerged on the scene, keeping their clients abreast of the court gossip. Lord Scudamore paid John Pory twenty pounds annually for his reporting. Meanwhile in France, nobleman and philosopher Michel de Montaigne, tucked away in his château between Bordeaux and Périgord, produced Essais, a collection of three books with 107 chapters. Montaigne, through formal and conceptual innovation, established the standard for contemporary essays and essay collections today: astute social criticism coupled with transparent, and often humorous, self-reflection. The combination of these historical phenomena—a burgeoning publishing industry, direct payments to reporters, representations of the self in essayistic form—bears a striking resemblance to the buzziest force in our current media ecosystem: Substack.


Indebted to direct payment plans in early modern England and the blogosphere boom in the early 2000s, Substack gathers disparate historical threads and ties them together in a neat contemporary bow, promising Substack writers and readers the opportunity to build a relationship à la Scudamore and Pory. Established in 2017, the platform enables readers to directly subscribe to writers’ email newsletters. While Substack takes ten percent of a newsletter’s revenue and the separate payment processing company takes another three, the system largely allows writers to build their own business model. As their website notes, “A few hundred paying subscribers can support a livelihood. A few thousand makes it lucrative.” For established writers on Substack’s platform, like Haley Nahman, a direct payment plan may exceed their full-time salary as a writer for a brand-name publication.


Salaried writers at named publications receive paychecks from their company—not their readers. In order to make money on Substack, however, a writer must commodify aspects of themselves for public consumption. The shift to subscriber-based compensation emphasizes the importance of the reader. Instead of writing toward the publication’s ethos, a writer constructs their own. Readers will fork over five dollars a month for intimate-seeming missives delivered to their inboxes from writers with a pre-established audience.


Initially known for hosting a coterie of semi-cancelled mainstream media mavericks, ranging from Glenn Greenwald to Leandra Medine Cohen to Alison Roman, Substack has only grown more alluring to professional and aspirational writers alike. In Clio Chang’s article in Columbia Journalism Review chronicling the recent rise of Substack, she linked the pandemic to the website’s growing user-base. Established journalists reckoning with the changing tides of media see Substack as a viable option for freelance work.


In an interview with Substack CEO Chris Best, Kara Swisher, host of the New York Times’ Sway podcast, suggests that the platform is derivative, and ultimately replicable. Perhaps Substack lacks originality, but its mission is clear: to support writers and readers, and allow writers who may otherwise be unable to access mainstream media byways to find a legitimate platform to publish their work.


When smaller newsletters with lesser-known writers explore their ideas, they escape the pressure to define their thoughts in marketable terms. For new writers, often young people publicly attempting to make meaning of newfangled observations, the writer-reader relationship largely develops without compensation. Without the looming presence of paying subscribers, the fledgling newsletter endures through sheer personal will. The individual reigns supreme in Substack, and the newsletter’s delivery hinges on the person—a person like Prem Thakker, CC ’22.


In the waning days of 2020 and part way through Thakker’s gap year, he sent off the inaugural article for his newsletter “better world.”— a writing project comprising reporting, conversations and essays from a “humanistic” angle. The first article concludes with a promise—that his newsletter will be “work that is critical of power, grounded in love & conviction, and built on the wholehearted belief that humans can actually be for each other, and not simply in spite of each other.” Starting from this idealistic premise, Thakker has written and sent off four additional articles to his subscribers.


One article dissects inauthentic calls for unity following the insurrection at the Capitol. Another investigates the story behind a viral television interview with a justifiably exasperated business owner, Dave Morris. This piece garnered attention, especially on Thakker’s personal Twitter, resulting in more subscribers from strangers.


“I'm not that renowned of a writer to offer exclusive content. I’m just going to write, to write,” said Thakker. “If you like it enough you can send some money, just because it takes time. Especially after the Morris piece, people randomly, from across the country, sent some money.”


Thakker’s latest essay, his most explicitly personal piece of writing, considers love through an anecdote about New York City’s recent snowfall. “better world.” reads earnestly, and perhaps any writing project—whether it be a weekly newsletter or the next great American novel—needs a dose of Wildean earnestness.


“If nothing else, even if a few people like it, that's great,” said Thakker, speaking of his newsletter’s reception. “And if nothing, nothing else, at least it helps clarify things for me or helps me work through things and try to grow intellectually myself.” At its most basic level, then, writing a free newsletter on Substack—sans editors, sans co-writers, sans institutional pressure—starts with the self. Whether the writer defines it as a serious journalistic project with robust editing or a receptacle for niche ramblings about local politics, the work is primarily mediated through the individual. This means a newsletter’s success—however one defines it—relies on the writer’s persona.


Grady Yuthok Short, a sophomore at Williams College and my former co-editor of our high school’s newspaper, chuckled at the idea of people paying to read his Substack, “Just Grady Things.” Evident from the title, his “newsletter-blog hybrid” centers on himself and his interests: sharing music from 100 gecs, Mitski, and Playboi Carti; analyzing local city council data; breaking down US-Tibet policy; and showing off his Tibetan terrier Khampa wearing a holiday-themed sweater. After seeing friends writing newsletters through Mailchimp’s TinyLetter last fall, Short thought to himself, “Wow, this is like Facebook, but healthier.” Unlike Facebook, however, the format facilitates fewer back and forth interactions between writer and reader. As much as a newsletter’s generation depends on the individual writer, its vitality depends on its community of subscribers.


“The downside of the newsletter format is that, just inherently, it’s sort of one-sided,” said Short. “You're just posting into the void. You’re spamming people’s inboxes.” Especially for Substacks without paywalls and thousands of active readers, a legitimate concern can creep into the corners of a writer’s mind: Does anyone actually read my Substack? In George Berkeley’s A Treatise Concerning the Principles of Human Knowledge, he questions if objects, like trees, exist without perception. Similarly, a writer may ask themselves: Does my writing exist without readers? Berkeley’s conclusion, “esse est percipi,” or “to be is to be perceived,” suggests the importance of active readers for writing’s existence. In an attempt to elicit honest criticism, circumvent the Internet void, and confirm people’s perception of his newsletter, Short created a Google Form.


“I wanted some way to know whether people actually liked or cared about what I was telling them, because if they weren't, I should probably be doing something else—or maybe not doing a newsletter at all,” said Short. “Since the subscribers are mostly people I know, and family members in some cases, I did think it would be nice to have a way for them to give me feedback in a way that wasn’t personal.” Within his newsletters, Short often includes particularly salient comments solicited from the Google Form. An anonymous subscriber responded to Short’s analysis of the final moment in Mitski’s music video for “Your Best American Girl,” presenting her perspective and recommending Summer Kim Lee’s article “Staying In: Mitski, Ocean Vuong, and Asian American Asociality” for further reading. “I thought the person offered a pretty cool interpretation of it. So that was nice. Free content, I guess, to share with everyone else,” said Short. In this way, Short intentionally creates an active dialogue with his readers—a dialogue that, in this case, lacks the toxicity of political arguments underneath a distant family member’s Facebook post.


Illustration by Kat Chen

The distinction between Substack and other social media platforms fascinates Tobias Hess, a junior at Bard College and creator of Substack newsletter “Gen Zero.” In his “About” section, he brands himself as a “concerned twink” thinking about Gen Z, technology, pop music, and activism. Hess appreciates the meta synergy between writing about “internet culture and the incentives of different platforms” and, by writing about this on Substack, participating in forming said culture. Commenting on the difference between Twitter and Substack, Hess said, “Mine's free, but let’s say you’re paying five dollars a month to get someone’s writing, the incentive is to be as thoughtful and helpful as possible because you’re doing a transactional service, rather than: ‘Ooh, if I’m super crazy online everyone will see me and I’ll get more likes.’”


Hess’ comments echo Sean Manaho’s in the Guardian. Manaho writes that Substack’s “micropayment platform for newsletters” will not eliminate all the issues plaguing media today—ranging from market demands influencing writers to debates about free speech and censorship—“but it will create space for writing not tailored to the trending on Twitter section, encourage writers to develop a deeper relationship with their audience, and promote the sort of writing (both longform and short) that doesn’t fit neatly into the categories of legacy media.” For those writing free newsletters, the platform still facilitates the writing that Manaho speaks of—work that makes people pause.


Hess is after this pause. In articles untangling “woke Instagram slideshows,” demands for “celebrities and influencers” to “use their platforms,” and algorithms decimating the concept of taste, he deconstructs Gen Z internet use. In doing so, Hess problematizes the various technologies’ impact on our collective consciousness. “I think that there's a lot of trends and ideas that get brought up uncritically,” said Hess. Substack allows the space for nuanced criticism to thrive. While Twitter limits wordspace and an Instagram slideshow limits visual space, Substack provides room to work everything out. Gen Zero “is for me, which makes it so much better,” said Hess. “Because now, when people have been responding and really reacting and disagreeing or agreeing, it’s always a surprise.”


Similarly, after realizing the limitations of sharing poetry on Instagram, Emily Freed, BC ’21, started her newsletter “Poemetry” on TinyLetter. On Instagram, she wondered if her followers cared about the poetry she shared to her stories. By starting a newsletter, she feels assured that her subscribers want a Mary Ruefle or Marie Howe poem accompanied by her commentary delivered to their inbox. This makes her “feel happy, like you're having a connection with them even if you're not that close.” Freed’s weekly writing process—curating poetry around an arbitrary theme, connecting selected pieces through written analysis, creating a digital collage for promotional purposes—has become a small, yet important, cornerstone of her weekly ritual.


Hess explained his writing process as an essential part of his existence: “My mind is so racing all the time so I kind of need to get these thoughts and feelings out.” Thakker, echoing Hess, noted the gap between experiencing something and understanding that thing. “Especially now, we are always thinking about things but aren't always fully allowing ourselves to chew on them or relate to them or understand them in terms of our personal connection to these things,” said Thakker. Presumably, in writing “better world.,” Thakker is able to chew on the morsels of his experiences; in writing “Gen Zero,” Hess can cathartically process his hot takes.


In his essay “On Experience,” Montaigne writes of humans’ neverending need to interpret our own lives. When someone relaxes in this pursuit, content with their understanding, Montaigne condemns them to “a particular weakness.” The mind needs to turn, “perplexing itself like silkworms.” Increasingly, Substack serves as the forum where young people seed their ideas, spam people’s inboxes, confuse themselves, and make their minds turn until something resembling knowledge appears.


Writers thread their thoughts into Substack silk and send it off into the abyss. Whether the newsletter is read or forgotten amid a mountain of email detritus is beside the point. Early modern newsletter writers attempted to make news—from Rome and Paris about the Catholic Church or the King of France, for example—legible for their readers. Likewise young Substack writers, without monetary incentives or externally imposed deadlines, attempt legibility in our illegible era.


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