Whatever it is you're seeking won't come in the form you're expecting.
— Haruki Murakami, Kafka on the Shore
4,150 miles. 100,000 feet in elevation change. Mountain majesty to ride-over country's waves of grain. "I'm going to do this as long as I can," Thompson thought, and what started out as a trick to get in more exercise by biking whenever he could in lieu of taking the subway culminated in 14-mile rides, then 28, then 50. Then cycling from New York City to Philadelphia and Providence, Rhode Island and Montreal. And one day, "I got on my bike here in New York, and I kept riding until I hit the Pacific Coast."
There was no medal at the end, no reward for having conquered the continent. "It was fun," says Thompson, "because I've met all these people and seen all these crazy nooks of the country." Biking around the city had given him a window into clean energy mobility, and so he'd started writing on his own about biking, walkable cities, and public transit. "This was me writing personal essays in a personal voice about my life and stuff I was doing myself, and was a little scary in a way."
Not for long, though, as readers loved the new window into Thompson's life. "People would have these wonderful conversations about what it was like," Thompson said of his more personal, bike and transit-focused writing. "It got me really excited about this." Editors, early on, weren't as interested, but as the clean tech revolution gathered speed, Thompson had a library of content to point to, and suddenly "I went from kind of tucking one little environmental thing into my coverage a year to 50 to 60% of what I write about now is this stuff," says Thompson.
It all started by deciding, one morning, to bike instead of taking the train. Then he kept at it, mile after mile, until he'd built the expertise and voice right when the world was asking for it. Suddenly writing about how "the U.S. could be a little more walkable, a little more bikeable" was landing new writing assignments, turning into the crux of his next book. Same for everything from biophilia, wooden skyscrapers, and solarpunk among Thompson's other diverse interests. "I have all these things in my head because I have been collecting them for this small but passionate audience in the Link Fest," he says.
The destination is nebulous
"When I started the newsletter, I had zero premonition that it was ever going to become something I made money off of," said Mario Fraioli of the morning shakeout. "Nor did I plan to write it for ten years straight. I was going to continue to write it as long as I found it interesting."
"I still try to hold by that."
But something funny happens when you show up, week after week, for years. Somewhere along the way to publishing your hundredth or thousandth issue, you'll stop and realize hey, I've built something. Something with heft, permanence, staying power. Something of your own. Something that matters to people. Something that defies definition, that morphs with your interests and opens new doors and closes others in the process. Something with a gravity that pulls you into its orbit, that eternally manages to be interesting.
"I will Google something very weird and narrow that I've been following for twenty years," says Thompson, with millions of published words to his name, "and the first hit will be a blog post I wrote in 2006."
It's that recognizable voice, honed over years of continuous publishing, that continues to bring in readers. "This is why a certain chunk of people get me," says Thompson. "They encounter this massive ice shelf of words that I've written, and they can get a sense of me through it." Unlike early cohorts of subscribers who are testing the waters, latter subscribers know what they're signing up for---and they're more engaged as a result. "I'm in dialogue with the same weirdos who care about the same strange things science and technology and culture that I care about."
"I write what I think is important," says Mark Hurst. "You can read it, or you can leave. I'm gonna be writing this either way. That's freeing."
The friends you make along the way
"The single biggest change," says Thompson, "is going from zero audience to one person." What starts as a watercooler chat becomes a keynote address. You go from saying what's on your mind to realizing that people are holding on to your every word. That takes you into a different mindspace.
"Once I got to maybe a hundred subscribers, I would get a meaningful number of replies," recalled Allen Pike, "and that was the thing that made me decide to put more weight on the newsletter."
You get accustomed to putting your thoughts out there, and then keep readjusting over time as your content changes.
People sign up to read about writing or running, news or nuance, but not about you as a human. Or so you think. "I was like, no one cares about a note from me," remembers Jane Friedman thinking of the early evolution of her then roundup-style newsletter. "They just want the tools or the resources, and then they want to get out. Who wants to spend time in an email?"
But then she added a personal note to the top of her Electric Speed emails, and discovered the "personal, more intimate side of email," in Friedman's words. "There are people who only want to read the note, and they don't care about the rest."
Once I got to maybe a hundred subscribers, I would get a meaningful number of replies.
— Allen Pike
Dave Pell, with his news-focused NextDraft, found something very similar. "I was among the first bloggers/newsletter writers to get a press pass to the Democratic National Convention in 2004," he recalled. "When I shared that news, I got a ton of responses and new signups. My readers were psyched about it. It was a good reminder that the personal connection to readers is the core value of newsletters."
And it's not just things that take the newsletter in new, more professional directions that get attention. "I get more comments about a mention of my beagles than I do about a mention of a news item," says Pell.
Those people who show up to cheer you on when you're cycling the States or on the convention floor can also come through when you'd least expect it. Readers would "send me things," ideas to include in his newsletter, said Thompson, and it hit him that The Linkfest "was becoming this social enterprise. I was actually learning more because it wasn't just me looking for stuff, it was other people who send me things."
"Several of them have become good personal friends over the last thirty years," says Thompson of his blog commenters and newsletter repliers.
It was a reader, a "recovering attorney," who took Fraioli's newsletter administration to the next level, when it started becoming a business in its own right. "He was a subscriber from early on, and was like 'Seems like things are going really well,'" Fraioli recalled. "'Yeah, they are, but the brand partnership thing is becoming a full-time job,' and he's like 'Oh, I could help with that.'"
It was another newsletter writer who helped Cassidy Williams turn her newsletter's sponsorships into a more profitable venture. "I had no idea what to charge at the time," she recalled. Then at an online meetup, talking to someone else with a sponsorship-powered newsletter, she mentioned what she was charging and they responded "You could add a zero to that." "It was very, very helpful," says Williams, and aside from paying the bills that the newsletter would otherwise incur, it "helps me stay consistent because I'm accountable to the people who are sponsoring."
Sometimes it's the little, indirect things that matter most. "One of the most valuable things that has happened to my list is when someone recommends you to their audience," says Jane Friedman. "And I try to do that as much as I can. When I find a newsletter or something or someone I really like, I recommend it in my free newsletter," paying it forward and building a mutually beneficial community, one link at a time.
A newsletter, if you can keep it
With hundreds of issues and thousands of subscribers on their lists, each writer started and keeps going for their own reason. Williams' newsletter brings in enough to pay its own bills, along with her childcare costs. Pell, Fraioli, and Friedman each turned their newsletters into businesses in their own right; Chatawan Mongkol plans to, testing the waters first with a tip jar and weekly sponsors. Pike's writing helps, in roundabout ways, seed interest in his businesses, while Thompson and Hurst both find newsletter writing to be reward enough of its own.
None of them had the path figured out when they started. They, to a person, built their business and longevity plans on the fly.
"Being a three-dimensional earnest human on the Internet and building trust over time with an audience is something that is really valuable," says Pike, "but you have to be really conservative about not mining out that value and hollowing out what you've built."
"The majority of your writing, ideally, should be helping the people who are reading," he continues, "and then over time you earn the right occasionally to ask for something back." And if writers like your work and are happy to cheer you on and support you when you share something personal, they'll be equally happy to check out your latest book or app or support your favorite cause if you don't make that the sole focus of your newsletter.
As long as you enjoy what you're writing, the path to monetizing your newsletter or turning it into something bigger isn't always so direct. It could be as simple as turning on a paywall, adding a tip jar, or bringing on sponsors. Or it could be as nebulous as your newsletter informing your other work in a virtuous cycle, and building your thousand true fans that you can lean on when the time comes.
"My money comes from my journalism," says Thompson. "My intellectual growth and self-satisfaction and ideas come from blogging and newsletters."
"The reward for having persisted for twenty-seven years is that I'm still here, and I still get to write and persist some more," says Hurst.
There's no finish line, no long-term goal you're shooting for with your newsletter. It's there, for as long as you can keep the streak going, ready for you to send out another newsletter issue whenever inspiration and your routine strike, filled with like-minded fans who've signed up for this journey with you. It, at its most basic, is a list of subscribers and an archive of what you've written. Thousands, millions of words, that somehow together are greater than the sum of their whole.
One day, you'll open a new blank page, stare down that blinking cursor, and type your newsletter's last word. But not today. Today, you're going to write and send again, winning the eternal battle against entropy one word at a time.