The definitive guide to newsletters
Your email sherpa takes you through a roundup of the best writing to grace our inboxes
We’re living in a newsletter gold rush.
All the talk right now, however, is about who’s making money from their emails. Today, instead, I want to celebrate some of the brilliant writing that graces my inbox.
My email reading and writing habits pre-date Substack, so let me be your newsletter sherpa and lead you through my definitive guide to newsletters.
Before I get into the recommendations, a quick word on how I read so many of them without getting overwhelmed.
Newsletters are the only emails I actually like to receive (besides the rare automated message from accounts payable telling me my invoice has finally been processed). I don’t like them to get mixed up in the crap of my Main Inbox, where they’re at risk of deletion in my frenetic attempts to reach inbox zero. Instead, I aggressively filter all my newsletters to skip the inbox entirely and whizz straight into a separate folder. I go in there whenever (read: daily) I’m looking for something to read. A tightly curated, personal newsletter feed; a much better scrolling alternative to Twitter.
Onto the recommendations!
The first newsletter is the one that inspired this entire post. A few weeks ago, the food and culture writer Alicia Kennedy published a roundup of her favourite “one-person operations driving this new form of food media”.
While I do love food, I don’t read Alicia’s newsletter for her recipes (even though they’re excellent). I read it for the cultural observations that fall between the cracks of the media cycle but are nonetheless urgent and important – and perfectly at home in my inbox.
Or as she put it herself: “In newsletters, everyone is making it all up as we go along, and I love that immediacy, that ongoingness, where we leave crumbs and threads untidied and pick them up whenever it makes sense to do so. Sensibility, not nut grafs.”
Journalists Emilie Friedlander and Andrea Domanic’s editorial strategy with The Culture Journalist, at least as far as I can tell, is quality over quantity. The pair produce a monthly newsletter-podcast hybrid and cover topics like parasocial relationships, the strange trend of clickbait restaurants and much more.
Ryan Broderick’s Garbage Day is a must-read for anyone who lives and works on the internet. Last week, he wrote a searing analysis about all the ways in which digital media is flattening the internet and failing its writers in the process:
I don’t want to make it seem like I’m saying working for Logan Paul or Smosh or Jerma or something is better than working at VICE. I’m actually saying the opposite. Both gigs are digital sweatshops and if any employees of Paul’s are reading this, you guys should unionize lol. But my point is that at least the influencers don’t have any illusions about what they’re doing. They know they’re making dog food for platforms. And they also seem to have a better business sense about the whole thing!
In 2014, David Carr described the writer and podcaster Ann Friedman’s newsletter as, “Tough to explain, easy (and enjoyable) to read. You won’t be sorry.” I’ve probably been reading Ann’s newsletter since that comment was first made and feel the same way about it today. It was the inspiration for starting my own newsletter and remains a shining example of the power of building a one-woman email empire.
Brad Esposito’s interview newsletter not only features people I want to know more about it, but he also asks them compelling questions. It’s a masterclass in the art of the Q&A (a format you’d think is easy but is one of the hardest to pull off). His recent interview with Hussein Kesvani is a stand-out example.
If you do any form of freelance writing for a living and aren’t signed up for Sian Meades-Williams’ weekly email, you’re missing out. Each week, she sends out a hand-curated roundup of calls for pitches and part-time writing jobs, along with excellent GIFs. BONUS: Along with Laura Brown, Sian also sends out the weekly lifestyle newsletter, Tigers Are Better Looking.
In response to a reader who worries that their happiness is an indication they’re a sellout, the internet’s kindest agony aunt, Polly, wrote, “Ask yourself how you feel more often, instead of trying to decide what you think and scrambling immediately for a verdict.” Heather Havrilesky’s iconic agony aunt column is now in newsletter form. Personal dilemmas solved in the intimacy of your inbox. Perfection.
PS Ask Polly is also a lesson in why you should always retain your copyrights! NY Mag used to publish Heather’s column (and the Awl did before that) and now she’s in charge of the operation on her own terms.
I’ve included the Quartz Daily Briefing in this list because it’s another OG newsletter that sparked a love for the craft of email writing. By creating content designed to be read in an inbox (rather than to drive clicks elsewhere), it paved the way for the editorial newsletters we’re seeing today. BONUS: A special mention also goes to Kevin Delaney’s Charter newsletter (Kevin was a co-founder of Quartz and mastermind behind the Daily Briefing, who’s now running his own media outfit).
Written by my podcast co-host, the Tiff Weekly is a playful newsletter. In each post, Tiffany Philippou returns to the themes of love, friendship and happiness but surprises you with every visit. It’s a newsletter I struggle to describe but love to read. I think it was the New Republic writer, Jo Livingstone, who called it parables of modern life. One of my favourite posts was a Q&A with a friend who took a different life path.
I have written for newspapers and magazines and I have written six books. For over forty years, anxiety was a constant work companion. It could just as well have been depression. Pick your poison. I assumed the pain was part of the deal, that if I was lucky enough to be able to write for a living, I had to pay a price. That is what I thought, until I started writing again, and discovered that maybe I had been wrong all along.
What if writing didn’t have to be so painful? That question is at the heart of Writerland, Columbia Journalism School professor, Michael Shapiro’s long-form newsletter. Shapiro is a writer’s writer and this newsletter is for serious readers.
An expertly curated roundup of the best writing, thinking and talking about digital nomads, borderless living and internet culture. Written by the journalist Lauren Razavi and my newsletter collective co-founder.
Katie Hawkins-Gaar’s Substack was one of the first I ever subscribed to; I must have discovered her around the time I moved my own newsletter over to the platform. What started as a creative outlet for her grief has become a manifesto for living. And it remains one of my favourite places on the internet.
Michelle Lhooq is one of the greatest cultural observers and writers of our time. She was on the frontlines of the #FreeBritney movement long before the big podcasters parachuted in and called it Urgent. Her gonzo dispatches about counterculture often feature ~real reporting~ and read like stories she’s telling you around the c̶a̶m̶p̶f̶i̶r̶e̶smoking area of the club.
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