How to Write a Newsletter People Want to Read

Several days ago, the latest newsletter from Samuel James hit my email inbox. I felt immediate excitement. I knew there would be something insightful, helpful, or interesting inside. But just below his email was a different newsletter (which shall remain nameless) that I deleted without a glance. Now, I can’t explain why I subscribe to newsletters I don’t read, but I do think I can explain what makes me want to read some newsletters and ignore others. 

The marketing gurus tell us subject lines and preview text are the main game—and to be sure, they are part of the game—but the simple truth is that without that preliminary emotional enticement, even the most finely crafted clickbait flunks its way into the digital trash bin. You can have the flashiest subject-line wrapping, but if the verbal burger inside is bland, processed garbage, then no one’s coming back. The inverse is also true. You might be the most mediocre subject-line punster, but if you deliver a juicy cheeseburger every time, then people will come back for more. They will forward your work. Yes, you may have fewer subscribers than the McDonald’s assembly line newsletters. But you will have more engaged, committed readers who actually benefit from your work. And isn’t the goal substantive quality, not hollow quantity?

Over the last five years, I’ve helped launch a half-dozen Christian newsletters that now collectively reach about 50k regular readers. So I’m definitely not in Golden Arches territory. But I do think I’ve learned a few things about writing newsletters that make your readers’ mental tastebuds water for your next digital dispatch:

• Treat your newsletter like a house show, not an arena. I’m not embarrassed to admit that my favorite concert of all time was Coldplay’s Viva la Vida arena tour. The only thing that could top that? A house show with Chris Martin, an acoustic guitar, and two dozen friends, because house shows are intimate, conversational, idiosyncratic, lo-fi, and deeply personal. They’re designed for the living room, not the arena.
  
  Likewise, newsletters play in digital living rooms: the email inbox. The same place readers get messages from coworkers, family members, and friends. It’s a living area, not a platform. Readers expect writing suited to that venue. 

That’s why the best newsletters aren’t afraid of personality, humor, and intimacy. You can have a few typos (though try to avoid them), crack a few jokes, invent some neologisms, and lean into your quirks. Don’t write in stodgy, professionalized, managerial prose. Instead, take yourself lightly. Contemplate darkly. Revel in ridiculous verbal flourishes. Your readers are the small club of people who want to have a conversation with you. They get it like no one else does. When you write for public blogs or outlets, you’re on the big stage. But in a newsletter, you’re beside the hearth, surrounded by your people. 

• Concrete hooks > abstract hooks. I’ve been to house shows where everyone talks over the musician. It’s painful. So if I ever met a musician in such a soul-sucking quandary, I’d advise him to do one thing: start with a banger.

If you’re writing about ideas, it’s tempting to introduce a concept with conceptual language. This is the way of the academy, and in this direction lies boredom. Now, I’m not saying the goal of a newsletter is entertainment. But I am saying that starting with a concrete illustration, word picture, or story arrests the reader's attention. It snaps a post’s “so what?” into focus and reminds readers why they shouldn’t move on to the next email.

It’s also good pedagogy. I imagine teaching ideas like building a picket fence. Ideas are the vertical slats. To hold them upright, you must connect them to horizontal cross bars—concrete stories. Without them, readers lose more than attention. They lose the thread of an idea. So begin by anchoring your abstractions with stories that make your newsletter’s ideas clear to readers. 

• Stay on message. Very few writers have something to say about everything. Even fewer have readers interested in everything they have to say about everything. There are exceptions (Tim Keller in the last generation, John Mark Comer in the current), but you are probably not one.
  
  So, if people sign up for your church newsletter hoping for devotional content, please don’t interrupt your regular programming for a hot take on global warming. Endeavor is focused on internet content, digital technology, and social media, so as interested as I may be in the latest presidential debate or string theory, it’s not the place for me to wax ineloquent.
  
  Of course, no one can stay on message unless they know what the message is. So what is your newsletter about? Bible study? Spiritual practices? Masculinity? Cultural apologetics? Political theology? Your readers subscribed to your newsletter because they see you as a credible expert on something. Define what that is, and work hard to stay in that lane.
  
  
• Newsletters live in medias res. If you’ve ever watched a movie that opens in the middle of a heist, fight, or action scene, then you’re familiar with in medias res, which is Latin for “in the middle of things.” In storytelling, this is the practice of starting a story not with “In the beginning” but with “So she took some of the fruit and ate it.” It not only grabs attention; it invites inquisitiveness. Why are we here? Where have we been? Where are we going? And these, of course, are some of the deepest questions any human can ask.

I realize that most people reading this aren’t writing fiction, but the same principle applies to non-fiction. In a non-fiction book, you use the introduction and first few chapters to set the stage. Introduce themes. Present questions the book seeks to answer. Establish a core thesis. You start “in the beginning.” But newsletters are an ongoing conversation between reader and writer. They start in the middle of things. Thus, the table is already set, and people are already eating. New readers understand they’re arriving halfway into a meal, and they expect no one to backpedal and re-narrate everything that’s come before (that’s what backlinking is for, by the way).

Far from being a nuisance, this is the excitement of a newsletter. The sense of being drawn into a community, into a private conversation only for those with ears to hear. Yes, that can generate confusion, but more often it generates curiosity. Conversely, if you constantly reset the table, you’ll bore established readers who expect a deepening discourse every week, not a discursive, repetitive loop.

• Fight for creativity and originality. I’ve heard it said that most pastors only have 10 good sermons, so they repeat them five times a year. Of course, there’s some truth in this, but in my own experience, this is only true of pastors who’ve lost their creative generativity. I understand the temptation to fall back on themes and ideas that played well in the past—and in preaching, this is often necessary to catechize new believers. But in the world of newsletters, it’s anathema. I’m not saying that you can’t revisit old ideas. I am saying that when you do, you should be expanding, correcting, or sharpening them. If you have nothing fresh to say, then don’t say it. The minute you do, the idea goes stale.
  
  As a writer, I know this is easier said than done. So, I’ve found ways to spur my own creativity. For example, over the last few months, I wrote 12 posts responding to individual chapters in Neil Postman’s Amusing Ourselves to Death. The posts weren’t reviews of each chapter so much as reapplications. I asked myself, “If Postman was writing this chapter today, what would he write?” Then I wrote that chapter.
  
  If you’re struggling with creativity, there is no substitute for reading and conversation. Digest what you’re reading in your newsletter. Try it on. Look at it from different angles. Expand on a chapter’s most prescient, pressing ideas. Likewise, find living conversation partners who can inspire you to think differently. Easily half of what I write begins over the dinner table with friends who challenge my thinking, ask a question I want to answer, or tell a story that expands my mind. 

I could add more to the list, but here’s the bottom line: newsletters are the most intimate space writers can cultivate with readers. They’re an ongoing conversation, focused on a clear set of themes, anchored by concrete stories in order to express fresh ideas.