Everyone should start a newsletter

The opening paragraph of an article or newsletter is one of the hardest parts to write. Because you almost never begin thinking about a topic at some logical starting point or follow a straight-line path to the conclusion. It’s more like being picked up by a tornado that swirls and slams you into a mess of points and counterpoints, cultural context and personal history, until you’re dropped backed to earth. Only then can you get an idea for where you’ve landed on a topic and the zigzagging path you were dragged along to get there.

It’s a common refrain that “writing is thinking.” But a lot of the formless thoughts spinning around in my head while I write never end up in a published article. So I prefer “writing is deciding what you think,” instead. You have to work your way back through the tornado’s path of destruction to rebuild and reorganize with intention.

It’s hard to write anything longer than a few hundred words without thinking carefully. And that’s why I’d argue that (almost) everyone should start a newsletter, and then mentor someone else to start their own.

Honing your opinions and beliefs in public

The idea that writing distills and solidifies ideas has existed across generations, cultures, and domains. Third-century Chinese poet Lu Ji wrote in Wen Fu (Rhapsody on Literature) that:

“At first words hang back, as though on dry lips; At last they flow gracefully beneath the moist brush. Like a firm trunk, reason supports substance; Like hanging branches, craft and skill bear fruit.”

Seven hundred years after Lu Ji, University of London professor Graham Wallas recalled a young girl wisely asking him “How can I know what I think till I see what I say?” But newsletters aren’t diaries or self-reflections. They’re public. And writing for others demands an even more rigorous kind of self examination.

In his book Smarter than you Think, Clive Thompson (a prolific newsletterer in his own right) highlights a study where students were split into two groups: One group wrote essays read by students in other countries, and another group wrote solely for their teacher. Essays from the group addressing strangers were consistently longer and better structured, something psychologists call the “audience effect.” They thought about their writing from the perspective of a complete stranger, assumed the stranger would be more critical, and were able to better red-team their own writing.

Thompson also cites a study from Andrea and Karen Lunsford, that compared the error rates per 100 words in student essays from 1917, 1930, 1986, and 2006. They found that rates were, on average, nearly identical. In fact, certain types of errors actually decreased in frequency, replacing the worry that texting and instant messaging would ruin communication with the possibility that more writing (even informal) produces better writing over time. The more that people write for an audience, the more they scrutinize and iterate their own words and ideas.

Scientists have known this for centuries, writing letters to their peers to sharpen theories with pen and paper. “The general conclusion at which I have slowly been driven from a directly opposite conviction is that species are mutable,” Charles Darwin admitted while working out his theory of evolution. He started with one belief and, through writing to a skeptical friend, ended up disproving his own idea.

The obvious steelman argument is that some people are more interested in entrenching and reinforcing harmful ideas than reexamining them. But I’d still rather those people write than not write. I just don’t want them to have a platform, which is not the same thing as writing. Algorithms spread controversy and negativity by design, they reward pointless flamewars. With Email, there’s no “Suggested for you” feed. You have to sign up for and opt into what lands in your inbox. And one of the best things you can do is share and link to edifying and uplifting writing and buoy those writers in whatever way you can.

If everyone started writing a newsletter tomorrow, you wouldn’t receive any more emails than you did today. You would have the option venture forth and find lists to join and authors to follow. Or wait for your own writing to bring them to you.

Finding your tribe with your writing

Another reason everyone should start a newsletter is because longform writing naturally lends itself to recommendations and outbound links to other newsletters worth reading. “I really wish every single person would write a newsletter. Not necessarily to make money from it. Not to quit their jobs and become a writer. Just to share what they're up to, what they're reading, what they're interested in. The number of interesting people I've met through my newsletter is just mindblowing,” Charlotte Grysolle posted two years ago.

With social media, there’s an innate incentive to appeal to the largest possible audience, diluting writing to its broadest appeal. The reward structures with newsletters are different turning comically niche topics into word-of-mouth machines rivaling algorithmic recommendations.

“I didn’t want a general public. I wanted a specific set of people, the people who could help me along as a human being obsessed with certain intellectual problems,” Henrik Karlsson explained when a relatively obscure essay topic spiked his newsletter signups. “I didn’t know who these people were. I only knew that they existed. Hence my writing was a search query. It needed to be phrased in such a way that it found these people and, if necessary, filtered others.” The more expert jargon and insider knowledge he included in this essays, the more interesting Henrik became to people as obsessed as he was. The world could use a little more topical eccentricity!

Take Tal Lavin and his editor David Swanson for instance. They’re eating their way through Wikipedia’s List of Notable Sandwiches as part of their weekly The Sword and the Sandwich newsletter. Each issue is filled with sandwich-related links, some academic and some silly, but often pointing to other newsletters. Lavin and Swanson have enabled comments on the newsletter’s archive page, receiving several after every send and often providing material for their next issue. The “content flywheel” might be cliche but almost nowhere is it as prevalent as with email newsletters and their reply loops.

“As you start routing information and putting out blog posts, you will begin to accumulate connections. Useful information will start to stream toward you, turning you into a small hub yourself,” according to Karlsson. “This will allow you to collect and curate information and route it back out, which will allow even more people to connect to you.” The more niche the topic is, the more your name will be associated with it, providing both a newsletter-as-resume you can point to and a monument to all your hard fought thinking.

Turning your story into a story

There’s something to be said for the fact that we have more than just Darwin’s Origin of Species, which is an invaluable contribution by itself. But we also have the thousands of letters that led up to it, an exhaustive record of Darwin’s breakthrough moments, failures, sidetracks, and backtracks. Without it, we would still have a theory of evolution, just a much less human version of it.

“Every week, after I hit SEND, it feels amazing. Not just because I’ve landed those planes, but because I feel like I’ve fulfilled a promise to you, and because I feel useful,” Mike Monteiro wrote in How to write it like you told it. “But also because I am reaching back through time and high-fiving an awkward fat little freshman boy, sitting at his desk, on the verge of tears because he’s struggling with putting words on a page, and I want to tell him that he figures it out.” If everyone started a newsletter, there would be infinitely more evidence that things get better and deciding what to think pays off in the end.

Honestly, Brenda Ueland made the argument better than I ever could in her 1938 book If you want to write. “But if (as I wish) everybody writes and respects and loves writing, then we would have a nation of intelligent, eager, impassioned readers...not mere critical, lodgy, sedentary passengers, observers of writing, whose attitude is: ‘Alright: entertain me now.’ Then we would all talk to each other in our writing with excitement and passionate interest.”

Writing publicly tame the tornado of thought to help you understand what you believe and why, so you can explain yourself so eloquently that others will find your writing and know you by your voice, even after you stop writing and sending. That’s why everyone should start a newsletter. Its default format is longform and simple, its delivery is permissioned and (mostly) decentralized, and, most importantly, because it belongs to you, forever.