Advice for newsletter-ers

There are so many email newslet­ters suddenly!

It used to feel cozy; a little neighborhood. But now, thanks almost entirely to the efforts of the com­pany called Substack, newsletter-ing has become the enticing next step for a whole host of writers.

I was just reading Patrick Tanguay’s thoughts about adding chunkier projects to his long-running Sen­tiers newsletter — which is excellent—and, in his post, he men­tioned an approach that I want to empha­size and sharpen.

Here’s my piece of advice for newsletter-ers, new and aspiring:

A per­sonal email newsletter ought to be divided into sea­sons, just like a TV show.

By “per­sonal” I don’t mean “diaristic” but rather “pro­duced almost entirely by one writer, in order to pursue some interest and/or estab­lish a small business.”

Here’s what you get from the nomenclature, the metaphor, of the “season”:

• a sense of progress: of going and getting somewhere.
• an opportunity for breaks: to pause and reflect, reconfigure.
• an opportunity, furthermore, to make big changes: in terms of subject, structure, style.

When do you break between sea­sons? Anytime! When life gets weird. When you’re feeling burnt out. When you sense a new obses­sion taking shape. When you want to bring in a guest writer. When it’s raining outside. Really: anytime.

Dan Hon was the first newsletter-er I saw to use this nomenclature. I am not 100% sure he is its originator, but that would not be surprising, given Dan’s crack­ling recom­bi­nant energy. His newsletter is all the way to season 8 now! Some of those sea­sons have been long, others short, and the gaps between them have been variable, too: many months, a few days.

A break, no matter how short, and a refresh, no matter how minor, is a shot of energy for writer and reader alike; totally a little magic trick.

But that’s all sec­ondary to this, the metaphor’s most precious gift:

• an opportunity to stop: gracefully.

Now, par­tic­u­larly if you’re begin­ning a paid newsletter with dreams that it will one day pro­vide most of your income, “stopping” is the last thing on your mind. “I’ll send this email newsletter to a happy, engaged audi­ence who will pay me $200,000 every year, forever!” You won’t — not forever. The fact that it feels so strange, even unpleasant, to con­tem­plate an ending before you’ve even begun — before you’ve enjoyed the tiniest sip of success — is pre­cisely why it’s impor­tant to do so.

Let me offer some specific examples.

The first is my year-long newsletter from 2019, which was titled Year of the Meteor. It was launched with an expi­ra­tion date, and I swear to you, that ticking clock was like a power source: a lump of ura­nium decaying, spraying off energy. I mailed an edi­tion every Sunday, always with the week number incre­mented in the sub­ject line. Everyone knew the denominator; it felt like a progress bar.

Email newslet­ters very rarely have progress bars.

The expi­ra­tion date wasn’t even binding! I could easily have said, at the con­clu­sion of that year, “What a ter­rific project! Let’s do it again. It’s time for a new newsletter; wel­come to the Year of the — ” whatever. I don’t think anyone would have been unhappy about that. And, if they were: what a con­ve­nient moment to step off the carousel. “Well, I liked the first season, but after that, the plot got a bit silly … ”

In fact, I did start a fresh newsletter later in 2020, chronicling the devel­op­ment of a simple video game. The pan­demic broke the project’s back. I haven’t given up on it, buuut, I’ve been too busy with other work to add a single line of code in months, so, that newsletter sits now in suspended animation.

The crisp­ness of my Year of the Meteor was the exception. In practice, basi­cally every email newsletter runs like my dev diary:

• Exciting launch
• Burst of confident, clockwork content
• Slackening of pace
• Newsletter with some variation of “it’s been a while!”
• Briefly renewed sense of purpose, energy
• Deeper slackening
•  … 

I will tell you — anyone has, who’s been through this cycle — it feels bad to have a channel out there, inert but never closed. If it takes a tiny bit of forethought, some cau­tionary design, to hedge against that bummer, it’s worth it.

Sea­sons aren’t right for every newsletter. My regular dis­patch to readers—which I’ve been sending con­sis­tently for ten years?? — doesn’t use that nomenclature, because its edi­tions are so spaced-out and irreg­ular that each is effec­tively a season of one. Maybe, instead of a TV show, it’s a lan­guorous sequence of art­house movies … 

Anyway, that’s my advice. Closing out, I’ll address a few poten­tial objec­tions to sending a newsletter with “sea­sons”:

It’s too cute.

Do you think it’s “cute” when a dark, gleaming HBO show pro­duced by ultra-professionals arrives in modular, gras­pable sea­sons? Come on.

If the pop­ular and prof­itable video game Fort­nite can swipe the term “season” for its evolving releases, so can you. I think it is well on its way toward a totally generalized, cross-media definition.

My newsletter isn’t going to evolve and change that much.

Maybe it should! But, okay: Frasier didn’t evolve and change that much, and it still had sea­sons. Turns out, they pro­vide a con­ve­nient, com­fort­able scaf­folding for any kind of ongoing cre­ative work. If nothing else, a season implies a pre­miere and a finale; don’t those sound like fun newslet­ters to write?

(If every­body starts doing it:) Every­body is doing it.

That didn’t stop you from starting an email newsletter 😝

November 2020, Oak­land