Sometimes magic is just someone spending more time on something than anyone else might reasonably expect.
— Teller, quoted by Allen Pike
"I was so motivated," said Cassidy Williams after sending the first issue of her newsletter. "I should write this every day."
"And then I stopped myself, because I knew that would be really hard to sustain."
Some newsletters are a sprint, a 5k race, a daily pop-up newsletter with a baked-in expiration date. Others are for the long haul. Twenty, thirty years, three or four million words, hundreds of weeks, one after another. They're a marathon, not a sprint. The only way you'll keep going, for the long haul or for a shorter, faster burst, is by building systems you can fall back on when motivation wanes.
"I have not missed a Tuesday," said Mario Fraioli. That's easy, at first, when you're motivated, when new subscribers keep showing up, when a reader sends a kind reply. It's far more difficult when you're tired, when your first child arrives on the scene, when someone sends an angry reply or unsubscribes, when your newsletter lands in inboxes and no one's there to read it. It's seemingly impossible to do consistently for a decade, as Fraioli has.
"The only thing that matters is your reliable publishing schedule," recalls Mark Hurst as the best advice he'd heard for keeping a newsletter going, from longtime blogger Justin Hall. "You have to be disciplined to keep that up."
Deadlines are your friend
Fraioli's virtual line in the sand, announcing his impending newsletter launch on the following Tuesday, got his first issue into inboxes on time. That same Tuesday deadline has kept him sending emails consistently every week since.
His goal is to write the newsletter early and "schedule it to send at 2:50 Pacific, on Tuesday mornings." Sometimes scheduling it requires burning the midnight oil, something it'd be much harder to find the willpower for without the looming deadline. "I've had a few nights over the years where I finished it around that time or a little bit later," he said, but it's hit inboxes within that time window every Tuesday, for well over a decade.
Clive Thompson uses his deadline as a way to focus his downtime. Instead of doomscrolling through social media, he'll read through his 150 or so RSS feeds, filing away things that could be worth including in his next issue before getting back to other tasks. "I know another one has to come out in a couple weeks and has to be filled with amazing stuff," he says. "There's an audience that's expecting it. The pressure is on."
I find the faster I write the newsletter, the better it is.
— Dave Pell, NextDraft
Deadlines set a scope for how much time you can spend on an issue. "It takes me about 4 hours a day to do NextDraft," Pell says, a focused time window that scopes the task of curating the best stuff from hundreds of RSS feeds. "I find the faster I write the newsletter, the better it is." The self-imposed time limit is a subtle quality control filter of its own.
Allen Pike, initially, thought writing routinely would come easy. "I'm independent. I can write as much as I want," Pike remembers thinking. "Then I'm swamped with all this stuff. There's always something else." The only way to send consistently was to "set a goal I would write at least once a month, and that's become basically the end of every month." That commitment made it easier to carve out the time to write and send the newsletter. "Without that self-imposed deadline, I will often just rewrite and diverge," he says.
Williams, after her early enthusiastic start, settled into sending her newsletter weekly, and "slowly but surely figured out how to write it consistently over time, which is very hard," she says. "There's going to be a day where you lose that motivation and discipline has to take over, which is very, very hard."
"If you're going to do monthly, do monthly. Weekly, weekly. Daily, daily," says Hurst. "Whatever you choose, that's what you have to do. 99% of the success of any newsletter is consistency."
That's because deadlines both hone your sending skills and make your newsletter part of your readers' routines as much as primetime sitcoms turned TV shows into cultural events before streaming smoothed out launch windows.
There's going to be a day where you lose that motivation and discipline has to take over.
— Cassidy Williams, rendezvous with cassidoo
"It's consistency and the predictability of when it's going to arrive," says Fraioli. "It's become a regular part of people's week. People write me and say, 'I read it while drinking my coffee before I get off my run on Tuesday morning,' or someone who's in Europe says, 'It's my lunch read on Tuesday.'"
"It has become almost a brand," says Pike of his monthly publishing cadence. "People will say, 'I missed your article. I just realized, oh, it's the third of the month and I hadn't seen your article yet,'" he says. That's enough motivation to keep sending on schedule.
And you might have to miss a Tuesday at some point, preoccupied at a work conference or, God forbid, a hospital stay. Missing one scheduled day doesn't mean it's all over. But it does mean you need to jump back in as soon as it's healthy to do so.
Stay curious
Deadlines and reader expectations keep the clock ticking. They don't excise the terror of the blank page, though. Inspiration is more fickle. Your systems have to continually give you new ideas to build into your next issue, paired with the confidence that subscribers want to read what's on your mind.
Pike's deadlines force him to save ideas for later. "I have hundreds and hundreds of drafts that are incomplete, and sometimes I'll come back to them."
Chatawan Mongkol turned newsletter prep into "an hour every day" project, cataloging the most interesting things he finds from feeds and Google Alerts in a spreadsheet. "Usually I have a pretty good idea of the top story by Monday or Tuesday," leaving the rest of the week to fill in the details before his Friday sending schedule.
Williams and Thompson alike weaponized their routine reading and online procrastination into an infinite source of newsletter ideas. "I started to come up with better systems," says Williams, training herself to save interesting articles encountered throughout the week to a bookmarking app. "When it comes time to actually write the newsletter, I can pull those links from there."
"I'm always reading stuff, and I'm encountering interesting things," says Thompson. "All my blogging has really just been eavesdropping on me as I'm talking to myself."
Usually I have a pretty good idea of the top story by Monday or Tuesday.
— Chatawan Mongkol, Soiciety
As your audience grows, as your newsletter takes on a life of its own, it's easy to forget that you're in control of what your newsletter becomes. "If you're comfortable writing in your own voice, it's much easier to keep up," says Williams. You started out writing for yourself; subscribers showed up to read that version of you.
"The only time I've felt burnt out or like I was off track was when I was trying to write about what I thought other people wanted to read," said Fraioli of a period in 2020 when he felt like he needed to share an opinion on everything in the running news cycle. Then he decided: "I'm going to chase my curiosity and my interests. Every good thing---the number of subscribers, the partnerships, other opportunities that have opened up---can all be drawn back to that," says Fraioli.
A steady source of material and a north star centered around the things you love are the antidote to burning out.
"I don't play to the audience," says Hurst. "I write what I think is important."
Tune out most of the noise
You shouldn't worry about stats. The issues you put the most effort into might not do as well as you'd hoped; the ones that blow up might be the ones you rushed out to hit the deadline. You have to keep hitting send, trusting that the consistent effort will pay off over time and that the weekly fluctuations are merely noise.
"I used to check stats daily," says Dave Pell. "These days, I rarely do." When he does check stats, he's focused on "opens (to make sure people like the newsletter) and clicks (to make sure I am sharing stories of interest to people)." Little else matters.
You get what you measure, Or more precisely, as Goodhart's law states: "Any observed statistical regularity will tend to collapse once pressure is placed upon it for control purposes." Jane Friedman has seen that in her writing as it has evolved over the years. "If I want to get a high open rate, I know exactly what to put in that subject line or what material to cover," she says. "But that doesn't interest me."
"There is a big danger in getting dopamine from numbers going up when those numbers are not actually forwarding any of your core goals," says Pike. "I have a preference to write to more people. That makes the work higher impact," and so checks total subscribers and which issues performed the best once a year or so.
"If you write for the love of the game," says Williams, "you get more genuine content." A friend's newsletter had 200,000 subscribers but negligible open rates, because he "optimized for maximizing subscriber eyeballs rather than for maximizing his own content," she shared. She optimized, instead, "to provide something valuable to people," and built a more sustainable business out of an audience a tenth of the size.
"I decided, back in 2002, that I only wanted to do it for fun and for social intellectual value," says Thompson. "That's why I've never really cared that much about the size of my audience." Hurst agrees: "I'm very excited whenever anyone subscribes," he says. "But because I'm not doing it for a living." With that focus, no stat other than consistency matters.
Mongkol instead, from the beginning, set out to build a business around his newsletter. What shape it'd take, that was yet to be determined, but the goal gave the stats meaning. "I write three-month reports to myself," he says. "The goal right now is to try to stay above a 50% open rate." That metric gives him a way to gauge success from promotions and ad campaigns. And when people unsubscribe, or reply with complaints, he sees it as a positive, honing his audience down into one that resonates with the focus of his writing. "It doesn't discourage me just because I'm not trying to get those readers."
Unsubscribes are, perhaps, the hardest stat to accept. "Early on, I would check every week who unsubscribed, and see if I recognized who the person was," admitted Fraioli, back when his list was mostly family and friends. "At some point, it got big enough that I stopped caring." Because the people who leave don't matter nearly as much as those who stay and keep reading years later.
"Every week, someone replies to the email and writes me back, and some of those people have been doing that for close to ten years," says Fraioli. "Those feel like more meaningful interactions," the things that matter far more than the daily ups-and-downs of stats and vitality.
I don't know at what point I'll have to say, I can't respond to everyone, anymore.
— Jane Friedman, Electric Speed
Even the positive stats, the growing audience and soul-feeding replies, have to be taken with moderation. Every writer we talked to intended originally to respond to every reply. Every one of them had to scale that back, over time, and learn to tune out the inevitable negative comments.
"I used to always respond 100% of the time," said Pike, but now, "I don't beat myself up if I miss one." The same goes for not taking annoyed replies too seriously. "You know you have something that's getting popular when people are taking time to tell you how wrong you are," said Hurst, and you have to rephrase the negativity in that light to keep it from discouraging you from sending the next issue.
Your strategies will change over time. Friedman mentioned wondering if she'll have to scale back replies, in the future. "I don't know at what point I'll have to say, look. I can't respond to everyone, anymore." The newsletter is, after all, the reason people signed up in the first place, the thing that drives the replies themselves.
"I try to respond," said Mongkol, after admitting that he's already had to stop replying to every message. "I appreciate when people reply. But I don't hold myself to it."
Because if you do, if you hold yourself to respond to every reply, to adjust course each time based on stats, you'll keep yourself from holding to your sending schedule. And that's the start of a death spiral for any newsletter.
The same goes for stats. "Something goes viral in Hacker News," said Hurst, "the clicks shoot up, and then the back side of the slope is a mirror image of the upside." If that whiplash feels too demotivating, if the stats become little more than distractions and heartache, you might go all the way and turn them off, as Hurst did.
Keeping at it, for the long haul
Writing a newsletter consistently is work. Hard, worthwhile work that's worth treating with respect. "My newsletters are my body of work," says Friedman. "When I die, I consider them more important than my books." Going at it haphazardly will prevent you from writing the newsletter your readers deserve. The only way to consistently publish instead of staring at the blank page when it's time to start writing, to ensure you won't burn out when everything doesn't go as you hoped, is to learn to focus on what matters and tune out the rest.
You can run a sprint, or a marathon, or a lifetime of marathons. The last option is equal parts hard and fulfilling because it often means admitting defeat in today's race instead of pushing through and showing up to the next race injured. Your deadline is an aspiration, a goal, a guideline to keep you on track instead of a set in stone law that you can't break even when you're at a breaking point.
Because the worst thing you could do is to flame out for good, halfway through your newsletter race.