Prologue“Eudora darling,” the letters would begin.
The paper yellowed, but the handwritten script very much still alive.
Katherine Anne Porter’s very intimate words intended for her friend and mentee, Eudora Welty, somehow in my gloved hands to be archived after the renowned Mississsippi author died.
During college I’d managed to land myself in a class whose primary project was to spend time IN EUDORA WELTY’S HOUSE READING HER LETTERS FROM FELLOW AUTHORS.
It was… literally quite literary.
And… almost voyeuristic, reading Porter’s words to Welty and escaping into their reality.
The latest news from Yaddo (the artist community in upstate New York where Porter lived) was mailed to Welty’s home in the Belhaven area of Jackson, where she’d returned to care for family after a stint in New York.
I became a bit addicted to the epistolary exchange, feeling as some fiction writers and film creators can make us feel: a bit too close to the story.
The way you’d feel if you’d found a box of your grandmother’s letters in the attic.
I’m reflecting on this at this very moment, fellow newsletterers, because I’ve begun to notice a lovely exchange that occurs after sending an issue of Opt In Weekly: a handful of repeat responders who send me their thoughts, to which I always reply.
What began as “Subscribe to my newsletter” has grown into real relationships.
And the exchange has inspired an idea I don’t quite know how to pursue: what if there were a newsletter that made you feel as if you were witness to the back-and-forth email discussion between 2 people?
“I think this.”
“But have you considered this?”
“Oh, that’s even better. Here’s my attempt at trying that…”
The way Porter mentored Welty, yet was her friend, too.
Is it far-fetched?
Would you enjoy feeling like you hacked an email account?
While I ponder that, here’s something for you to consider:
Make your reader feel as if you are writing to them alone. Newsletters as a genre allow senders to create that sense of intimacy. Immerse in it.
A Few Announcements
Congratulations to Opt In Weekly curator and commentary writer Samantha, who had a baby earlier this week. We’re so excited for you!
Thank you to Seth for helping with commentary this week. We did it!
Opt In Weekly is taking a spring break vacation next week while I enjoy some family time. See you in 2 weeks.
It was Monday.
9:45 a.m.
I got 3 consecutive text messages from 3 different moms on a field trip with my 9-year-old daughter Josie.
Each contained a photo of her from a slightly different angle.
And each induced a parental urge to get in my Jeep and drive to the local natural science museum, find her, pick her up, and make things better.
But my rational brain knew that by the time I arrived, the moment would have passed.
The terrible, terrible moment.
The one that unfolded after they called for volunteers and all the children nearly burst from wanting to be picked.
And she WAS.
They PICKED HER.
Do you remember this feeling?
It was magic, right?
Getting selected out of the crowd to do something important.
So Josie, thrilled at this opportunity, stood with 2 other 4th grade girls and followed instructions:
“Close your eyes and hold out your hands.”
Y’all.
Those instructions alone foreshadowed a questionable ending, right?
The first object they were handed was a pipe cleaner.
Easy enough.
But then the process was repeated and
OH
GOOD
GRACIOUS
It was a SNAKE!
In these photos her skin is bright red.
Her face is mid-quiver.
She looks completely tortured, the 6-foot snake spread across the hands of 3 girls while the speaker holds it near the head, which is inches from Josie’s terrified face.
She doesn’t want to talk about it.
But she did say that she was somewhere between calm sobs and pure hysteria.
Yes. She rates her emotions. She has so many of them.
And had she known that getting picked would mean holding a snake she would have hidden under her chair.
When she got home, we hugged.
I told her I was proud.
She’s glad the whole thing is over.
So… newsletter creator, here’s the thing:
How do people end up on your subscriber list?
Make sure to set clear expectations.
And, if you’re using some sort of lead magnet, make absolutely sure that it’s so aligned with your newsletter content that wanting one means they’ll actually want the other. Better yet, earn a separate opt in to the newsletter.
I’m not saying your newsletter is the snake in this story.
But I am saying that some emails/newsletters have a way of slithering into my inbox uninvited.
Y’all, I want you to meet Louis (Louie) Pecan.
He’s our first family pet.
We waited until the girls were 9 and 11 to take on the challenge of taking care of an animal.
1.5 months in and so far, so good.
He’s a Yorkie, in case you’re curious.
And he’s done a wonderful job of stealing our attention away from screens.
But, beyond the fact that he’s incredibly adorable, why mention him in a newsletter about newsletters?
Well, let me tell you about how he responds when the girls get home from school.
Most of us have witnessed or experienced a dog’s joy at his favorite person’s arrival, right?
This 3-pound ball of floof can hardly contain his excitement when he senses the school bus is near.
I’ve literally felt how intense his emotions run when he sees it pull close while holding him in my hands.
His heart races.
His tail twitches.
His entire body is restless with pure anticipation, and then, JOY, as a sweet reunion unfolds.
Goal: Send a newsletter that inspires even a fraction of this type of excitement upon arrival.
How? Talk to your ideal readers and find out what they really want and care about.
Earn their puppy love.
For 4 mornings in a row, my family has been uncomfortably anxious.
Why?
The school bus tracker app, which shows us exactly where the elementary school bus that picks up our youngest daughter, HAS NOT BEEN WORKING.
Y’all.
It’s glitched every once in a while throughout the year, but never for 4 consecutive, frustrating days.
“But, Ashley,” you say.
“Can’t you just take her to the bus stop a little before the time when it should arrive?”
And this feels logical.
But 6:37 is rarely when it actually makes the stop.
Some days it’s 15 minutes ahead.
Some days, 15 minutes later.
And, I don’t know about you, but making educated guesses at the crack of dawn (sunrise was 6:41 a.m. this morning) isn’t my strongest skill set.
I err on the side of DO NOT RISK MISSING THE BUS.
Because missing it means an hour of your life shot sitting in bumper-to-bumper traffic on 2-lane roads that weren’t planned to accommodate thousands of frustrated parents and little ones.
So, for the past 4 mornings, we’ve been checking the app (which, for some reason, works like magic in the afternoons and gives us false hope for the next morning), complaining that it’s not working again, and feeling absolutely blind without its guidance.
“So, how does this help me make my newsletter better?” you ask (clearly the repetitive rough start to the day has me hearing voices).
Here’s how:
If you stopped sending (just as the tracker has stopped working reliably), would your subscribers feel anxiety or frustration?
Or would they not really notice?
Aim to be critical, or at least semi-critical.
Or, perhaps, enjoyably episodic?
Enough so that they’d notice your absence.
I’m not saying go wreck their mornings with a no-show every so often.
But, it’s actually healthy if your readers depend on you for a specific reason.
It strengthens your relationship with subscribers when you send what you say you’ll send.
When you… actually deliver, right?
Your newsletter should provide a value they’d rather not live without.
Be the reason they don’t miss the bus.
Every year for Valentine’s Day, my husband writes me a poem.
I say “every year”…
He probably missed a few here and there.
But it seems like every year.
And this has been going on since before we got married, so, roughly 18 years.
Having typed those 5 sentences I now feel bad about any time I’ve complained that he’s not romantic.
He makes it a performance:
Me listening as he reads rhyming couplets in a sing-song voice.
Him delivering inside jokes with a sneaky grin to see if I get them.
I usually simultaneously laugh and cry.
And I imagine as he drafts each one he is doing so in anticipation of the moment when I experience his creation.
There is a bit of “Thank God you remembered I love this” mixed with an appreciation for him setting aside time to make me feel something.
Additionally, there is a more holistic emotional response.
The compounding result of a tradition lived out over and over again.
Nostalgia mixed with something new.
It’s sappy and lovely and I’m proud it is ours.
It reminds me of an elderly couple we befriended years ago who seemed still so very in love.
The wife told me that part of what held them together was that despite any frustrations they might be feeling, he took time each day to sing “You Are My Sunshine” directly to her.
It had come to mean, “Remember, I still love you.”
And so, as all the balloons, chocolate hearts, and commercialized festivities begin to crowd our lives this weekend, perhaps it’s a good time to think of your newsletter as a love letter to your reader.
One written with the intention of helping them feel
Loved
Valued
Appreciated
One created for the moment when you deliver the inside joke and they get it, hit both by the dopamine of the moment and the compounding emotion of feeling it on repeat.
I often curate email list growth stories, and some of the tactics they promote can feel a little hacky compared to this simple approach:
Show readers you love them through what you send…
So much so that they share the way it makes them feel with others.
Not because of some big “Share this” CTA you make prominent in the content, but because what you’ve sent prompts the action without begging for it.
And, if you fancy it, maybe try a poem or an unusually sappy introduction.
Do your readers suffer from inbox fatigue?
Of course they do.
So why should they choose to open your newsletter amidst the barrage of information and spam cluttering their inbox?
Michael Aft (formerly of The New Paper) said it best when he spoke at Newsletter Fest last year:
“NEED to Have trumps NICE to Have. So much so that I would say that if your product is just nice to have you shouldn’t start your business.”
Ouch.
But, also, true.
Because why create something that is easily scrolled past, unopened, unsubscribed to?
If your goal is to run a newsletter that people actually read, you’ll need to do the following as you strategize content:
1) Understand the competitive landscape
Who else publishes a newsletter about this topic? What do they specialize in?
2) Find a gap in that landscape
Is there a “need to have” itch that no newsletter is actually scratching?
3) Create an unfair competitive advantage
Lean into your talents to deliver a newsletter that would be difficult for someone to replicate. That sometimes requires having a unique point of view and / or the ability to curate and make sense of information your audience will find extremely helpful or entertaining.
Your goal is for your subscribers to smile (or at least mentally smile) when your next issue arrives.
Because nice to have turns into “why am I subscribed to this?” after a while.
Be the reason they still open emails.
Teach them they need to have what you send.
Do you ever think about your newsletter in context of the volume of interactions your subscribers process in a given day or week?
How many emails does your reader receive in the same hour yours arrives?
How many Slack messages?
How many texts?
Or Facebook, LinkedIn, Instagram, TikTok alerts?
Our lives have become a barrage of little red circles—sometimes ovals when my unopened email count hits triple digits!—we chase around the screens we sit in front of and carry.
All of them beg for our attention and are prioritized according to hierarchy.
And it’s no wonder the email inbox is difficult to win.
So many senders abuse it, teaching us to expect content we don’t want and sometimes didn’t ask for.
In The Subversive Genius of Extremely Slow Email, Ian Bogost examines the idea of slowing down, and the potential of technology to help us recapture a less alert-driven existence.
“Our suffering arises, in part, from the speed and volume of our social interactions online.”
Reading his piece made me think about Wordle, a lovely word puzzle my co-workers have been playing daily. We share our scores in a Slack channel.
My CEO JD Graffam captured its refreshing qualities one day:
“Wordle is not an addictive or abusive game, like most games, and I love it. No red badges, no endless play, no notifications, no ads, presumably minimal tracking (it does have google tag manager). I love it, but I do wonder why it’s worth the maker’s time to maintain. Surely all the scaling has come with a cost and significant investment in time.”
And while we could dig into the business bits, what I’d like you, newsletter creator, to ponder is what it would mean for your newsletter to be like Wordle.
It does several things at once.
It provides a reason to focus.
It rewards critical thinking.
It connects you with the people with whom you share your scores.
It builds a relationship at a healthy cadence.
It delivers a gratifying (or frustrating) experience, but does not ask for more.
I go to it. It doesn’t nag me.
All goals we might seek to achieve as we land in the inboxes of the endlessly notified recipients who might enjoy slowing down to learn and then share what you’ve taught them.
“What is it like inside your brain?”
Kate Harding posed this question in her essay about how people have forgotten how to read critically that sent me down a sort of thinking-about-thinking rabbit hole last weekend.
And while I could make a day of analyzing her entertaining attack on modern readers who take everything a skilled writer publishes hyper literally instead of understanding and appreciating the intended joke—ok, you need more context:
Heather Havrilesky, humor writer and advice columnist at The Cut published an essay, “Marriage Requires Amnesia”—an excerpt from her forthcoming book, “Foreverland: On the Divine Tedium of Marriage—” in the New York Times.
The subhead: “Do I hate my husband? Oh for sure, yes, definitely.”
Twitter went crazy with accusations that the relationship should be over and that Havrilesky’s husband should be outraged, because, as Harding (whose essay I read) suggests, people don’t read carefully anymore.
“Reading can make you feel close to someone without actually knowing them, a precious gift in a lonely world. But if the pleasure of reading is feeling connected to a distant stranger, then the pain of watching people read badly is its opposite: a severing of shared humanity.”
Harding laments that the Internet has hastened the speed at which readers who “don’t get it” attack the people and ideas they’re misinterpreting.—Ok, I think you’re up to speed. Thanks for indulging me.
The thought this sparked for me is how important it is for creators to focus on their best-fit readers and try not to worry about the rest.
What do I mean by that?
And how does it apply to your newsletter and/or other creations?
Understand the people you want to attract and serve.
Write for them.
There will be people who don’t make it past the subheading and go act like you’re an idiot on Twitter, but they aren’t your people.
The ones who get it and defend you are.
And you want them out there, writing essays about essays defending you.
And subscribing.
And sharing your work.
And amplifying what they appreciate about what you create.
They are the ones who want to know what it’s like inside your brain.
Keep letting them in.
Now, onto the newsletter news. There’s some interesting stuff this week.
“I’m trying to decide if I want to buy 3 King Frogs to feed snacks and mash into a Mega Toad or just find a Mega Toad someone has already made.”
Coming from my 9-year-old playing Roblox, this might have made sense.
But the utterance came out of my middle-aged husband’s mouth over the weekend and I had to laugh aloud.
“Come again?”
Then he went into detail and explained how an NFT creator had released a limited number of frogs that could be turned into toads that were going to be pretty valuable. The frog traits and snacks you bought them would dictate the toad characteristics, and the rarer the better.
If you’re asking “What’s an NFT?” (and I know you are, Dad), you’ll probably want to Google it for a technical answer because my understanding is very basic: it stands for Non-Fungible Token and feels like the digital art collectible equivalent to Garbage Pail Kids.
And while I may scoff, my husband has been in an I-can-learn-new-things mood for the past 3 weeks and he and our daughters (9 and 11) have been discovering a world the girls understand much more quickly than he or I do: that people really like buying, owning, and selling digital pieces of a gamified story.
Or at least that’s how I’m interpreting the facts that have trickled down to me.
And it reminds me of an article I obsessed over and shared last year from Andre Chaperon and Shawn Twing about worldbuilding.
The idea is that instead of creating a “community,” which is getting very buzzword-ish these days, you build a world your audience can inhabit.
“Instead of using aggressive direct response or media production approach, we build ‘worlds’ for our audiences to inhabit. Worlds that acknowledge their implicit and explicit motivations, show them better ways to solve their problems, meet their needs, fulfill their desires, and position ourselves as trusted, caring fiduciaries.
Our approach is inspired by writers who build worlds that capture their audiences’ attention, immerse their readers in a story that feels real in every possible way, and pulls their readers forward page by page, scene by scene with narrative tension.”
My reason for loving this approach is hinged on my love for literature and getting lost in a story, especially if it offers a different reality with specific societal norms you have to understand for context. I love that sense of escape.
I encouraged newsletter creators to build worlds with their newsletters, or make it a part of a larger world they’re building.
And now I’m starting to see NFTs for what they are:
Pieces of the worlds their creators have built.
Parts of stories people want to inhabit.
We can scoff at the art and say, “Why invest in that?”
But if thousands of people are vying to own a really unique King Toad, someone has done a successful job at creating the story that got them there.
People are moving into the world of NFTs and creating their own worlds within it.
Alien Frens are invading.
CryptoBatz are about to be released.
Potential Web3 newsletter goal: build a world in which people are having late night discussions about how to live in it.
Make it feel like an escape.
Maybe even get subscribers on the edge of their seats waiting for the next release.
Ok, let’s get to the curated links.
