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.
#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.
#“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 g
