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I Used to Run a Popular Newsletter. Then Things Started Getting Weird.
June 9, 2024

I Used to Run a Popular Newsletter. Then Things Started Getting Weird.

Reading Time: 5 minutes

You Might Be Creeping Your Favorite Newsletter Writer Out, The intimacy and vulnerability of email gave my readers the wrong idea—and they expected me to be everything for them., Newsletters: The Substack boom is creating parasocial relationships right in

‘I consider you my friend.’

I looked at the name of the email’s sender to see if I recognized it. This wasn’t the first time I’d received a personal message like this from one of my 10,000 newsletter subscribers. Over the course of six years running a weekly newsletter for freelancers, I’ve read everything from confessions, complaints, and demands, to life stories—grievances of all kinds really—and expressions of support and appreciation. Among the positive feedback was a subcategory of emails that was at once flattering and unsettling: ‘You’re my friend.’

On one hand, what newsletter creator wouldn’t want their work to resonate with their audience so much that it drives them to reach out? On the other, how does a creator navigate the responsibilities and expectations of a parasocial relationship that formed without their buy-in? Is it now their obligation to not just provide customer service, but be a ‘good friend’?

‘If someone takes the time to cross the digital void, the least I can do is respond,’ Ryan Broderick, the creator of Garbage Day, a newsletter devoted to web culture and technology with over 70,000 subscribers, told me. He explains that even if someone writes something mean, the fact that they took the time to write anything at all, and write it privately, is an honor.

Writing an email ‘isn’t performative,’ he continued. ‘I find the incentives of sending someone an email to be much different than the incentives of tweeting or making a TikTok about someone, because they’re not doing it for any attention other than for your attention.’

Once maligned as teenybopper, kiss-your-Elvis-photo-goodnight foolishness, parasocial relationships have gained credibility as a valid psychological phenomenon. The first time I heard about them was after news of John Mulaney’s divorce hit the internet. On a date soon after, the guy I was with railed against the comedian’s behavior as if he, a social worker in Brooklyn, had a personal stake in the matter. Podcasters like Joe Rogan or Andrew Huberman have earned an audience of devoted fanboys, Peloton instructors have their groupies, and every fitness influencer has a bevy of followers at the ready to buy whatever they might be selling, as if purchasing a protein shake gets them one step closer to a meet-and-greet. And of course, there’s Taylor Swift and Beyoncé.

The more platforms that are available for connection and content creation, the more opportunity we have for forming these emotional imbalances. I’ve confused podcast conversations with my own, conflated what I read online with my own ideas, their jokes with my jokes. Sometimes someone who follows me on Twitter but has never met me in real life will say, ‘Oh, I know you!’ upon meeting me. Not ‘I know of you,’ but ‘I know you.’ It’s not intentional; the mindless churn of consumption and production of content makes everything a little blurrier.

According to a survey conducted by Storydoc, 90 percent of Americans subscribe to at least one newsletter. In 2023, Reuters reported that in the United States, 8 percent of news subscribers ‘pay for a newsletter written by an individual journalist or influencer and 5 percent pay for a podcaster or YouTuber.’

On the creator side, as of 2023, Substack boasted more than 17,000 writers publishing paywalled content—while many others publish content for free. Mailchimp, another popular newsletter platform, touts 13 million users. Meanwhile, the newsletter creation platform Beehiiv has 20,000 active newsletters, according to TechCrunch.

For any newsletter, there may be thousands or even millions of readers. Or your kid or neighbor wrote it and you’re holding down the title of ‘audience’ all on your own. Unlike on TikTok, Twitter, or Instagram, where you know exactly how many people are vying for the creator’s attention and can adjust your expectations of an interaction as needed, newsletters offer no such reality check. Regardless of its popularity, it’ll be delivered directly to your inbox, where it’ll snuggle up next to your personal emails, camouflaged by its standard display name and email address formatting. So, for a second, you might think, ‘I can’t believe Obama is saying ‘hey’ to ME!’ For all intents and purposes, it might as well be an email just for you. It comes regularly, always, or close to always, on schedule.

As with every other email in your inbox, though, you’ll get to it when you get to it. In bed. In the bathroom. In line at the grocery store. On the treadmill. At the doctor’s office while wearing nothing but a paper gown and a pair of socks. Wherever you and your phone go, the newsletter and, by extension, its writer goes. No wonder it feels natural for readers to consider newsletter creators a ‘friend.’ You won’t find anyone more accommodating and, as is often the case with writers, more vulnerable.

‘I write very personal stuff about difficult experiences, and when somebody writes me back and says, ‘You just named my experience. Thank you,’ I love that,’ Sari Botton, a bestselling author, editor, and founder of the newsletters Oldster, Adventures in Journalism, and Memoirland, told me. She notes that Oldster alone has 43,000 subscribers. ‘I’ve had elderly people write to me and say, ‘Thank you for your newsletter. It makes me want to keep on living.’ I’ll take that any day.’

However, there’s also a tension—one that’s grown with the ‘proliferation of newsletters’ and social media, Botton explained. Since it’s so much easier to correspond with writers, it’s also easier to ‘misunderstand the boundaries’ of that relationship.

The immediacy of every digital interaction also creates a mirage of familiarity. Once upon a time, fan mail went to designated post office boxes or managers’ offices. Some stars would read them. Someone might even respond on their behalf. In elementary school, I wrote the Ty Beanie Baby company a proposal for a new bear and they responded with a kind note. And that was the end of that. It didn’t cross my mind to send them a follow-up message; it was clear that this new bear concept was not up for discussion.

Today, that’s no longer the case. The walls separating the consumer from the creator have practically vanished. They can slip into that TikTok creator’s DMs. Or sign up for the podcaster’s Patreon and chat with them on Discord. With newsletters, people expect more from the writers they see in their inbox every single day, whether that is camaraderie, advice, a conversation partner, or a meek projection of a person they really need.

In my public farewell letter announcing the recent acquisition of my newsletter, I told my subscribers sentiments I’d suppressed for years. ‘I no longer have it in me to be a secretary, therapist, researcher, editor, mentor, fundraiser, phonebook, HR department, small claims court, spokesperson, mediator, and bulletin board for a community that needs far more than what a handful of freelancers and grassroots initiatives can offer,’ I wrote.

It wasn’t a complaint; in most cases, I put myself directly into those roles, never stopping to consider the consequences of marketing myself as everyone’s everything or of sharing the intricacies of my depression with an audience of empathetic readers. That’s part of the reason why my readers so often reached out as if we were friends. After all, one email could truly lead anywhere. A response. A new pen pal. A mentor. A soul mate; the fantasy of transcending digital or societal boundaries has never felt more attainable.

Or nothing at all.

‘It’s tricky,’ says Botton. ‘I don’t want to piss anyone off. I really aim to be kind. But I also just want to put out my newsletter.’


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