Most newsletters would benefit from being time-boxed or run in a “pop-up” style. That is: Seasonal, or with a hard stop.

Set a limit of three to six months and pick a frequency — perhaps once or twice weekly? — and a word limit — maybe 500 words? (something you can’t shirk away from, that you could refine in an hour if hard pressed) — and stick to your rules like a madperson.

Ignore how many subscriber you do or don’t get. The goal is to build a habit of writing and publishing. If you successfully pull off the writing, fantastic! Repeat. This is how large bodies of work are produced: Via a consistent, gentle, pinging into the aether of humanity.

If you plan to charge for your newsletter, I’d recommend doing so only after you’ve written one or two seasons. If you’re unprepared, charging for a newsletter and feeling beholden to paying readers is a great way to burn yourself out.

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#Endings

Over the last two years I’ve run three, free, pop-up newsletters: The SMS Project, Pachinko Road, and Where are all the Nightingales?. Each was daily, all ran for about a month, had thousands of subscribers, had crazy-high open rates, engagement, responses, and when they were done, I deleted the lists. Poof.

There’s something powerful about knowing an end exists — for both writer and reader.

As a writer, I find having a backstop keeps me motivated. During this recent Where are all the Nightingales? newsletter, which I wrote while walking some 430 kilometers, I wrote more — in more states of exhausted delirium — than ever before in my life. Despite the rigors, 30,000 words were produced, and I was mainly able to do so because I knew the production schedule wasn’t endless, that if I got to day thirty, I’d be done.

Eleven p.m., zonked, with miles to walk the next day, I managed to find some reserve of creative energy and write and publish. When a newsletter (or any project, really) extends into the dark undefined infinitude of the future, it’s much easier to skip the work and say: Aw, heck, I’ll just do this tomorrow. Forever pushing ahead to some theoretical “tomorrow.”

To beat a dead horse: Deadlines are probably the most powerful tool for subverting our inner procrastination dingdongs. Seasonality means the recurring deadlines themselves will end. It’s a great combo.

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#“High-value” Readers

I’m not sure this is empirically true, but it feels generally true: The more attention a reader gives your work, the higher their “value.”

I find this framing useful because it helps me think about where — as a writer — to channel my energy.

In my experience, a newsletter subscriber is a higher value, higher attention reader than someone who only follows you on Instagram or Twitter or TikTok. From high-quality attention flows literal economic value: I sell significantly more books when I pitch 10,000 newsletter subscribers than 35,000 Twitter followers.

The highest-value readers, though, are probably those who buy and read books, because this requires the greatest commitment of attention. These are the readers most likely to go to bat for you and your work out in the world. Books, in this way, represent a special overlapping of attention, idea density, and (potential) economic sustainability.

It’s for this reason (and more!) that the main thrust of my online “work” is to build an audience for my books. I do this mainly by funneling potential readers towards mediums of high(er)-quality attention, like newsletters.

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#Booooooooks

I wrote more about the why of books in my 2020 membership program roundup:

A billion tweets fade instantly. A thousand copies of a book will be with the world for at least a few centuries. A thing to be found by a future hilltop bunkerchild: pizza … toast? Maybe these timeframes are equally irrelevant within the long-now, but the mediums of print and tweet and the output produced therein feel spiritually antipodal. When I post a tweet I almost always think: Ugh, what am I doing? When I finish writing a book I almost always also think: Ugh, what am I doing? (Because making a book is such an arduous undertaking, like running a dozen marathons in succession.) But! The path to the book — collimating experiences, working through thoughts, iterating on ideas into that final book form — nourishes and challenges in ways I fail to believe a million tweets ever can.

A book is a creative distillation more dense than a hundred newsletters, which themselves are a creative distillation more dense than a thousand tweets. As distillation increases, so too does difficulty. But that difficulty flows from the very opportunity to iterate and refine. You learn to see that difficulty as a positive signal, that you’re probably on the right track.

As a writer, once you’ve experienced and understand the power of iterating on the scale of books, it seems kinda obvious to align your work and life around the act of making of them. I’ve come to see newsletters — and the pop-up newsletter in particular — as a key part in this book making process.

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#Tired Readers

2020 (and 2021 to a lesser degree?) was The Great Year of Newsletter Mania, driven in part by a flood of venture capital into the ecosystem. This capital increase lead to a bunch of Old Media Brand-Name Writers (and some history professors) getting Big Cash Dollar Paydays from, mainly, the newsletter upstart, Substack. The buzz of the money unleashed a torrent of other newsletterers.

Naturally, I suspect many readers out there are experiencing a bit of newsletter fatigue. There are simply so many, with many being editorless and therefore operating at whoa-hold-on levels of loquaciousness, and frequency (again?!), and on a whole they’re multiplying in ways that can make a dreary inbox an ever darker. So the pop-up newsletter — the very quality of being limited! — can subvert this feeling, may replace the sense of endless content doom with … lightness?

For Where are all the Nightingales?, many replies arrived long after the newsletter had finished. Folks saved them, like a little booklet, for later, when they had the time and attention to give. They were able to do this because they knew it ended. It’s a much more difficult ask to save a newsletter that continues forever; the value of a missed issue of an infinite series is zero. Whereas, the value of each issue of a time-boxed series maintains (one hopes!) a sustained and meaningful value.

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#Paid Newsletters

I don’t charge for my newsletters. I like the NPR-esque model of “unlocking the commons” and I’m lucky enough to make that work. My pragmatic goal in writing my newsletters is to maximize reach (within the context of the stuff I write about).

Instead of charging for newsletters, I run a membership program, the proceeds from which fund the freely available work. Members get a bunch of perks, but the most obvious perk is a big discount on my books and photographic prints. I see these memberships as little down payments on my future book work (and as such try to return the entire cost of membership each year in discounts). And members get the added benefit of some behind-the-scenes meta discussions (via zoom, livestreams, et cetera) around my work. Those meta discussions help me work better and more thoughtfully. They never feel like a burden, mostly help me improve as a writer, photographer, or bookmaker.

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#But Why Newsletters?

Personally, for my online work, I try not to overly rely on upstream actors (i.e., social networks). Ideally, you should be positioned such that if Instagram or Twitter disappears tomorrow, your work would not be (dramatically) affected.¹ This is why email can be so powerful. Email-based newsletters, and their (mostly) inherently decentralized nature, insulate you from negative or disastrous future changes to how social media — or other similar networks — function. ²

I find that Twitter and Instagram are good nets for capturing general attention around my work. I use them to funnel folks to my main newsletter, Roden, which I started back in 2012 and send monthly and acts as a kind of catch-all for updates on my projects. In a way, Roden forms the core of my “online presence.” My ur-newsletter. From Roden I seed my pop-up newsletter readership, asking readers to help spread the word on social media. This constellation of a core newsletter birthing shorter-term pop-up newsletters helps create mini-“events,” which help introduce folks to my SPECIAL PROJECTS membership program. And then those members become the groundswell audience of my books. The pop-up newsletters themselves often seeding those very books.

This whole goofy dance feels like a durable, self-contained ecosystem under which I maintain (I think?) a healthy amount of control.

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#Write and then Write More!

Anyway, I’m a fervent acolyte of newsletters in general and, in particular, the pop-up variant, the newsletter run in “seasons.” My newest seasonal newsletter runs on a 21-week cycle and it’s just about to end. That feels glorious. I’m energized both to have it end and think about what another season might bring. It’s a photography-focused newsletter and the seasonal quality helps me winnow down which kind or location of photos to focus on for this round.

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With most creative work, the trick is to focus on habit formation. Somewhat counterintuitively, don’t aspire to be someone who writes a book — don’t be a sucker waiting for “inspiration” — instead aspire to be someone who writes on schedule. Books naturally flow from rigorous writing habits.

I’ve talked to many creative folks who have burned out. Usually, the burnout happens from having bitten off too much of an undefined thing. So my usual advice for someone who wants to get into the newsletter game is to set a goal with a clear finish line, and one that isn’t years out. Pick a frequency (daily? weekly? monthly?), slap an end date on it, stick to the schedule like your life depends on it and call it a “season.”

A pop-up newsletter is a superpower — readers tend to be more excited to subscribe to something that ends, and writers tend to be more motivated to commit and bring their best self knowing that it doesn’t drag on forever.

If you start one, please let me know.

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#Noted