(Originally published on The Brevity Blog)
I sent my first email newsletter nearly 20 years ago, in 2007. And it was awful—not just the content (which wasn’t great), but everything about the process of writing it, designing it, and sending it.
At the time, you had to hand-code the message, send it through a PHP list, debug broken layouts, and pray nothing exploded when you hit “send.” I was working in a small office and that newsletter got passed around like a hot potato among the staff and a rotating cast of interns.
No one wanted it. It felt tedious, technical, and disconnected from the “real” literary work we cared about.
And yet, no matter how hard I tried to get away from the task of sending out the newsletter, I kept getting caught holding that goddamn potato.
Eventually, I realized that when life gives you, um, potatoes make…the best of it, right?
So I started paying attention to other newsletters: the consistent generosity of Seth Godin, the fearless curation of Austin Kleon, the thoughtful exploration of Craig Mod, the staggering openness of The Daily Rumpus. I got curious about and played with the form, injecting some voice and personality and flavor into our spud-like email: letters from the staff and micro-essays from our readers and links from stuff around the web. And over time, I saw firsthand how creative and personal and even—sometimes—easy a really good email newsletter could be. The more we pushed and played, the more every conceivable metric increased: subscribes, opens, clicks, sales—and even direct replies from readers. (Worth noting here that ease and enjoyment do tend to correspond with list growth … but not always.)
Now, much of my work—and creative—life centers around email newsletters. Since 2019, I’ve personally sent or assisted others in sending thousands of email newsletters. Not only do I curate two personal newsletters, one focused on my creative practice and one on my professional practice, but I’m the co-founder of a literary magazine that publishes a flash essay every week directly in our subscribers’ inbox. I also work one-on-one with writers and artists, and consult with publishers and organizations, to help them start, build, and/or grow their own email newsletters. And guess what:
Email newsletters are still one of the most powerful, versatile, and human tools we have for finding readers and keeping them close.
Look, I get it, every “build-your-author-platform” article ever written since the dawn of the internet has said very clearly: YOU MUST HAVE AN EMAIL LIST!! There’s no shortage of prescriptive advice and templates and “best practices.” But honestly, that much advice often just creates confusion.
Instead, I think we can start with two simple rules:
RULE 1: You have to *want* to newsletter. It has to be a choice, not a chore.
Interest is contagious. So is disinterest.
You don’t need to love every send. But you do need a genuine reason for showing up. Curiosity. Enjoyment. A sense of ownership. A feeling that this newsletter gives you something, not just your audience.
When a newsletter works, it’s usually because the person writing it finds the format meaningful. They see it as a space to think out loud, share ideas, tell stories, connect dots. Not as a box to check or a series of marketing announcements when you have something to sell.
If you don’t want a newsletter, don’t start one. And if you already have one you dread, that’s not a discipline problem—it’s a signal that something about the format, frequency, or focus isn’t aligned with your goals.
RULE 2: Readers have to *want* to be on your list. You must offer something of value, and people must choose to sign themselves up.
Your value doesn’t have to be flashy or transactional. But it does have to be clear: insight, perspective, entertainment, usefulness, reassurance, inspiration.
And crucially, readers have to choose.
No scraping email addresses. No adding people “just this once.” No treating your list like a captive audience. A healthy newsletter is built on consent and expectation: readers know what they’re signing up for, and they want more of it.
These rules are complementary. You’re interested enough to show up consistently, and they’re interested enough to invite you into their inbox.
When both sides want to be there, everything else—open rates, growth, longevity—gets easier.
Two rules. No “hacks” required.
You don’t need to master every tool or follow every trend. You don’t need to “optimize” your landing pages or start a Substack. You need alignment: between you and the work, and between the work and the reader.
I don’t have all the answers when it comes to email newsletters. In fact, I have yet to discover some perfect formula. But I know this:
Interest is everything.
When I’m interested, readers can feel it. When they’re interested, I can feel that too. And that’s enough to keep me sending.