Email Secrets Of The Masterminds Behind The Most Popular Newsletters

The writers and editors of Lenny, MarketSnacks, and FiveThirtyEight’s Significant Digits weigh in.

Email Secrets Of The Masterminds Behind The Most Popular Newsletters
[Photo: SuperStock/Getty Images]

“Everyone is bad at email, every single person you know or will ever correspond to,” says Walt Hickey. The FiveThirtyEight journalist who writes the site’s daily Significant Digits newsletter, lays out this theory to me in—what else?—an email. “If you think you’re good at email, you’re probably not, but even if you are good at it, so what? That’s like being good at dirigible piloting or equestrian competition or cursive.”


Then comes the good news: “Realizing that everyone else also hates it means that it’s that much easier to be done with. Eighty percent of the time people will be happy if you reply to their email with a sentence fragment.”

Whether or not you agree with him on either point—that email is obsolete or that responses aren’t mandatory—Hickey is right that most of us agonize too much and for too long over email. He should know; as the brains behind a popular email newsletter, it’s Hickey’s job to think strategically about emailing. So I asked him, along with the writers and editors of other major newsletters, to share how they’ve learned to manage their own inboxes.

Blocks And Bylines

“Your inbox doesn’t own you. You created it. Don’t let it push you around and let its demanding emails run your life,” Nick Martell and Jack Kramer, cofounders of the financial news newsletter MarketSnacks explain in a joint email. “To deal with that, we’ve got a two-part strategy: blocks and bylines.”

The first part is about time management. Martell and Kramer say they “schedule blocks of time during the day exclusively for emails—one in the morning for an hour and one in the afternoon.” This helps avoid that “scary, monotonous cycle of email after email after email after email.”

The second part is to “secretly prioritize the senders. Your buddy Tim or Dave (and, of course, mom) are cooler than your boss in real life. But when facing your inbox, respond to your manager first since it’s likely time-sensitive,” they counsel. “A person related to an important task at hand gets priority. It’s that simple.”


Scan Subject Lines And Delete Without Mercy

“I delete pretty much anything that is unsolicited PR,” admits Jessica Grose, editor in chief of Lenny, the email newsletter created by Lena Dunham and Jenni Konner.

Grose, who wagers she gets around 200 emails a day,  says she “can usually tell from the subject and preheader of an email what needs an immediate response and what I can save for later.” Martell and Kramer agree this is pretty easy. “Most emails are lamely commercial (shocker, another sale at J. Crew) or boringly social (a 37-email–long chain on where to have brunch Sunday).”

For some, that means deleting with abandon. “If I can’t tell if it needs a response instinctively and immediately, I delete it,” says Hickey. “I’m pretty easy to get ahold of, so if it’s really important they’ll find another way,” typically by following up or taking to Twitter.

Hickey offers this wonderfully simple rule of thumb: “If you think it might be spam, it’s almost always spam.”

Don’t Reward Bad Subject Lines

As Martell and Kramer put it, “You live and die by your subject lines. We make ours intriguing and catching so you want to hear more about ‘Lululemon stock’s awkwardly downward-doggish strategy.’ The same goes for yours,” they suggest. “‘Just checking in’ is an email subject-line recipe for ‘ignore.'”


Grose says that writing Lenny has helped her get better at this. “I definitely try to put more clear, concise information in my subject lines than I used to. I never use a generic ‘Hey’ anymore. Gotta get people to click!”

Hickey also opts for clarity but is less interested in capturing recipients’ attention. “I get responses from readers more, which makes feedback instantaneous and me more likely to read—and thus write—shorter, more casual notes over email,” he says. “Casual email is the way to go.”

Flag Now, Reply Later

Just because you don’t instantly delete it doesn’t mean it deserves an instant reply. Says Grose, “My filing system is if something needs a response, I keep it marked ‘unread’ until I answer.” So do Martell and Kramer, who think of their “inbox block” periods as “e-triage.”

“If you try to tackle emails throughout the day,” they point out, “they’ll keep popping up and you’ll never get actually work done.” After first opening messages from senders whose “names you immediately recognize,” they move on to any subject lines that sound genuinely high-priority (to them, not just to the sender). Then, like Grose, they “mark the longer-responses as ‘unread’ to return to after.”

Weekly (If Not Daily) Inbox Zero

According to Martell and Kramer, “There are two types of people in this beautiful world—Inbox 18,233 and Inbox 0.” But as they see it, the latter is unnecessary on a daily basis but can be smart as a weekly approach. “You just can’t always get to everything before the Rangers hockey game is on at 7 p.m. But before a weekend it’s cathartic.”


Martell and Kramer commit to replying to everyone who contacts them within 24 hours. “Since our readers are devoted to opening our MarketSnacks emails every day, then we’re excited to open and respond to all of theirs.” This rule of reciprocity, they say, “gives us e-karma and happiness.”

Grose and Hickey, both more inclined to forego responses, are stricter inbox-zero devotees. “I go to sleep every night at inbox zero,” says Grose, and to help her hit that target, she spends 20 minutes each morning “cleaning out what piled up overnight.”

But when I ask Hickey if there’s anything he considers a bad emailing habit he’s found a way to live with, he names inbox zero. “I have no idea why my brain craves it but it’s a constant schlep. I think it’s worth it—sometimes I’ll look at another journalist’s phone and see ‘29,039’ unread emails and I start seeing stars.”

Hickey adds that he mentioned my inquiry into his emailing habits to a friend. Her advice to him? “Don’t ever respond to his email: This is a pro move. Then years later, be like, ‘Ha! That was just my bad habit flaring up again. I’ve learned to live with it.’ And be at peace.”

“Not gonna lie, there was a non-zero chance that was how this almost went down. That’s a bad habit I’ve come to live with.”

About the author

Rich Bellis was previously the Associate Editor of Fast Company's Leadership section.