What Kind Of Project Is A Daily Newsletter?
Meta-thoughts on a disciplined but creative endeavor
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One of the meta-questions I think about sometimes is what exactly these publications the industry calls “newsletters” really are. Obviously it depends on the writer, and I suppose there isn’t a single answer. The format itself is closest to old-school blogs; Substack and the other similar platforms are a lot like WordPress, only with payment processing built in.
But Substack and similar sites are not the only things that get called “newsletters.” Lots of publications, like magazines and trade publications, also have what they call newsletters, which are often columns with a topical focus, or fleshed-out industry-news bulletins.
I’m old enough to remember when the word “newsletter” brought to mind a soporific, ink-jet-printed letter with updates about some little organization (“A FINAL UPDATE ON THE UPCOMING BAKE SALE…”). So it’s interesting how that term ended up becoming the name for this major writing/media format.
But more specifically than that, what I’m thinking about here is the nature of what I’m doing with my newsletter. What kind of endeavor is a daily newsletter based on a topic (cluster of topics), but fundamentally creative as opposed to analytical or journalistic (though of course there are elements of those things in much of what I write)?
There are different kinds of formats and media products that I think of “newslettering” as being like in some ways. I’m sure that I think about this quite a bit more than any of you, and I wanted to share some of these behind-the-curtain meta-thoughts.
The (self-imposed) deadline pressure of writing almost every day probably sometimes results in less thought-through stuff than I would write without that constraint; but that fast pace also serves as a discipline that generates more good ideas than mediocre ones. The flow and the routine, to me, is inherent in the enterprise, as opposed to the less time-bound creative projects of, say, writing books or recording studio albums or freelancing occasional magazine pieces.
You could say, for example, that writing one of these newsletters is a little like having a radio show. But I think it’s held together thematically a little more than that. One way I think about newslettering, with an emphasis on the daily (or just often/regular) aspect, is that it’s like writing a comic strip. Given that they’re about recurring characters with slowly evolving but more or less fixed personalities, there’s a broad set of themes and settings that have to be held to.
But there are mechanisms for exploring other kinds of topics or settings within the constrained world of the strip, and as a kind of creative professional I kind of see the techniques going on. The only one I’ve ever read much of (of course in book/collection form) is Bill Watterson’s Calvin and Hobbes, so I’m thinking of examples I know from that strip, but this is probably true of many long-running comic strips and of the format in general.
Some ways to grow the strip world are to have occasional strips that focus on tangential characters and their interactions with a less central regular character (Calvin’s Uncle Max interacting with Calvin’s parents); have strips that take place during vacations/road trips/events; “dream” or daydream strips where only a single panel at the end grounds it in the “real” world (a bunch of panels of Calvin’s mother in the kitchen throwing harsh chemicals at an octopus, etc. etc., followed by her scolding him for not touching a totally pedestrian dinner); social-commentary strips, like the infamous “deer hunting” one, where Calvin giving an absurd presentation at school that gets him into trouble is merely the delivery mechanism for a serious-not-serious commentary on overpopulation discourse.
In other words, there are layers to the craft and subject matter here; it’s a matter of creative and technical proficiency alike to find ways to kind of get outside the constraints of the endeavor while staying true to it; growing in a way that feels continuous with what came before while also being in some ways fundamentally different.1
As I’ve been writing this daily newsletter for almost five years now, I’ve become aware of these sorts of double techniques, that serve a practical or professional purpose for the creator but also a sort of in-universe purpose for the reader. In this case, “I don’t feel like writing just another strip where Calvin makes fun of Susie or gets in trouble with Mrs. Wormwood or breaks something in the house” gets expressed by Bill Watterson as the introduction of the Spaceman Spiff character (how Calvin sees these arguments with the cast of characters in his own head) or the invention of something wacky like the transmogrifier or the time machine or the wagon that works as a spaceship (to allow Watterson to, for example, remark on nativism in the “Weirdos from another planet” story arc).
The way that comic strips form story arcs while also working as little standalone vignettes is also very much how I see the sweep of a few months, for example, of my newsletter.
For example, I write these longer pieces to coincide with my discounts, every Christmas season and every week of my newsletter’s anniversary in April. I think of these special-week pieces as roughly analogous to major magazine features, TV specials, music singles. But I also craft them to be longer and more thought-out pieces on whatever I’ve been especially probing throughout the year. So they’re also analogous, a little bit, to the openers and closers on an album, giving the whole year a kind of loose structure or theme. And the pieces in between often have a loose continuity.
So a little more on the “double” techniques. One of the things I’ve started doing, now that I have nearly five years of daily pieces in the archive, is to think about what deserves a revision, or sequel, or follow-up, or just to be presented again with minimal edits or updates.
One of the constraints you run into doing this for years is 1) always having a fresh idea and 2) what to do once you’ve “used” a great idea. How do you keep it in currency without just writing the same basic thing over and over, which I never want to do? How do you turn this pile of old content into a back catalog instead of a dustbin?
That fits with the story arc bit, because I think of the newsletter as an ongoing enterprise, with each piece not quite a standalone piece of writing, but like little episodes in a broad quasi-narrative. And I’ve come to think, after really quite a lot of thinking, that you can’t be overly worried about originality or too scared of “self-plagiarism.”
Some folks are snobbish about that, going beyond the literal presentation of old work dishonestly as new work, but acting like you can never touch an idea again once you’ve touched it once. That’s not how writing geared towards presenting and developing ideas (especially, as here, alongside and with input from an audience) works.
It’s also not how other creative people work. Take, for example, bands and video game developers. It’s industry-standard stuff to issue singles (usually but not always on an album, so sold twice) and then over the years to compile and sell greatest hits collections. It’s also common to release the same music not just on different formats, but over the years in slightly different ways: a remastered edition, a box set or collection, etc. Some of this is a cash grab, but some of it adds value. It’s also pretty common to issue compilations or remakes of popular video games from older consoles, with some bug-fixes and minor gameplay updates (e.g. to the control scheme or the saving mechanics.) Sometimes there’s even some archival or historical material added in.
This is the way I’m thinking about my new “Archive Dive” feature. Yes, it’s a lifeline if I don’t have something really worth publishing on a given day, but it’s also new content for the majority of my current readers. And most importantly, it’s an opportunity to revisit something worthwhile, make it a little better or add an addendum, and basically say, “Hey, I still think this, and I can’t say it much better or differently so I don’t want to either rewrite it or have it be locked away forever because it isn’t ‘new content.’”
So the radio show (not really), the comic strip, and the album (albums with a kind of loose theme/intuitive flow) are creative formats I see some similarities with in how this newsletter goes together and comes out.
The obvious and closest one, though, is the magazine. I came up with the idea for The Deleted Scenes when I left my first magazine job and basically applied everything I learned about web publishing to my own work.
Of course, with the exception of an occasional guest piece, it’s a “magazine of one.” You could say I’m the contributor, the editor, the writer, the headline writer, the copyeditor, the art director, and the social media promoter. I do all of those things for every piece every day. In fact, I’m so used to it that I almost forget there are so many distinct roles and tasks at play in publishing something regularly at a high level of quality. The actual writing is only a part of it!
So that singleness, and the flexibility it entails, is why I don’t think of this as a magazine. But what distinguishes this and innumerable other good single-author newsletters from blogs, I think, is the polish and presentation: the production value. If you have that discipline, you can enjoy the format of a magazine with the flexibility of being your own editor.
One of the things I enjoy most about this process, in fact, is the illustrator/art role. I almost always use photos of my own, some of which I take as part of working on a specific piece—like my illustrated visit to Middleburg, Virginia or other pieces of that nature. Some pieces I illustrate more conceptually, essentially using my camera roll as a stock photo library. (I took a photo of a quirky clock at a thrift store with the price tag on the clock face once; I dug it up to illustrate a piece titled “The Time Value Of Money.” Once I found a product at the grocery store with a $5 price tag and then right next to it a “manager’s special” discount price tag for $4.99; I used that to illustrate a piece about inflation.)
On the point of being your own editor, another thing I’ve realized is that the newsletter format is very well adapted to the “pointless deep dive” genre—i.e., pieces that an actual editor of a publication would probably have to decline as being too random and too long.2 “Pointless deep dives” are some of my favorite pieces to read and write, and often do well traffic-wise. I want to call out another newsletter here, Snack Stack, whose author does great deep dives related to food products, marketing, etc. My most recent entry in this genre is this piece about the afterlife of a failed video game console’s case.
Usually these long stories exist in a findable form somewhere, but have not been compiled, narrativized, and presented to a more general audience. In the one about the game console, almost all the sources I found are Reddit threads on video game subreddits, and YouTube videos on video game channels.
Being able to take in all of that stuff, pull out the main points, trace some leads, and tell a complete, sourced story about a thing, is so cool. If the story makes some bigger point—like some observations about mass manufacturing I made at the end—even better. But not necessary. These kinds of stories are perfectly adapted for the newsletter format.
I suppose both because I’m good at it and used to it, I forget that it’s actually pretty impressive to maintain something like this, at a high level of creative and technical quality, for this long. And when I think about it that way, I probably do a better job.
At least, I hope you think so.
Related Reading:
There’s Something About Blogging
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The way we should hope to see our built environments and communities grow
“This thing exists and it is interesting” is 100 percent a valid reason to write an article about it. The idea that everything needs a shoehorned news hook to make it relevant is silly. I think that’s probably largely about screening out all sorts of subpar submissions, but it also probably spikes some really fascinating stuff.