***

Liza asks:

“This is a bit of a long shot, but I am desperate. I’m repeatedly getting asked to remove the em dash from email copy. By the CEO. To avoid looking like copy is written by AI.

“Its purpose and use is defined in writing guidelines. But I feel like I’m fighting a losing battle here. I refuse to stop using it entirely. Because it genuinely adds so much value to written copy. ARGH!

“How would you approach this? Education? Stubbornness? Or just cave? 😞”

* * *

OK… <cracks knuckles>… I’m here for you.

You don’t have to have a nit-picking CEO to question your em dash choices. Maybe you’ve seen this sentiment:

“As soon as I see an em dash, I stop reading.”

A line in the sand drawn because AI loves em dashes. Ergo, anything with an em dash must be AI. 

That’s like saying Batman wears a cape, so anyone in a bath towel is Batman.

* * *

This CEO’s real concern probably isn’t the em dash itself. It’s a worry that OTHERS might glimpse an em dash and—aha!—accuse you with hot self-righteousness of AI slop. (That last sentence contains an em dash, by the way. Actually, two. Lovingly placed there by me.)

Em dash panic has created a strange new form of reputational self-surveillance. We are treating a normal punctuation mark like contraband, and asking good writers to pre-defend normal writing choices from imaginary accusations. WHAT ARE WE EVEN DOING.

Anyway. I could really get annoyed about this. (And I will, in a second.) But I’m also practical and I want to help Liza: What do we do?

A few thoughts:

>>> Lead with nodding agreement, then reframe. (Good advice for life, not just em dashes.) Something like:

“Listen, boss. You’re right that AI often overuses the em dash. And I understand the concern that people may now associate it with AI. But AI also overuses bullet points, punchy one-liners, raccoons-in-trench-coat metaphors, goblins, and words like quietly and delve and it’s not-x-it’s-y.

“So the fix isn’t singling out punctuation and executing it at dawn. The long-term fix is using our tools with enough judgment that the copy is unmistakably ours.”

That shifts the conversation…

From: “Ban the em dash!”
To: “How do we make our writing feel intentional, specific, human, warm, and only ours?”

And it signals something important: You do think about this. You are not using punctuation by accident.

>>> Show, not tell. (Also good advice for life; are you writing these down?) Pull a few examples where your em dash is doing its job. Ones you love, where it’s creating pace, emphasis, contrast, surprise, a human little turn of thought.

Then pull a few examples of AI-sloppified em dash installations, where the dash feels lazy or overdone. Line them up, side by side. Help your CEO see the difference.

Don’t point out merely that a sentence has an em dash. Point out why the em dash earns its place, and how and why you can’t imagine any other punctuation there without completely ruining the flow, meaning, or drama of a sentence.

An em dash doing its rightful job:

“There are many em dashes in this book—too many to count, although you’re welcome to try—each one handcrafted and tenderly set in place.”

The two dashes create a quick, self-contained aside—a little wink to the reader before the sentence resumes. It has pace. It sounds like a person having a thought in real-time.

P.S. That sentence may be part of the dedication of my new book. Should I actually dedicate it to the em dash? Hit reply and let me know.

An em dash doing someone else’s job:

“There are many em dashes in this book—each one serving as a powerful tool for emphasis, clarity, and flat-out drama.”

Here, the em dash is just a runway straight into the ocean. Nothing turns. Nothing interrupts. Nothing is revealed. The words after the dash simply continue in the same-same direction. A comma would do the same job:

“There are many em dashes in this book, each one serving as a powerful tool for emphasis, clarity, and emotional resonance.”

The differences are subtle but real. Here’s the two-second test I use:

The difference is not dash vs. no dash.

The difference is whether the dash creates a meaningful pause, a turn of thought, contrast, surprise, a human aside, or emphasis that the sentence has actually earned.

A useful em dash is a hinge. It turns the sentence.

A lazy em dash is a fog machine. It makes things feel dramatic without making them clearer.

That is the conversation worth having.

Not: “Does this punctuation look like AI?”

But: “Is this punctuation doing real work?”

Finally…

>>> Offer a usage guideline instead of a ban. Like: “How about we set a standard instead? One or two em dashes per email, max. Never as a lazy trailing thought. Always when another punctuation mark (a comma, a hard stop in a sentence) won’t do.”

It’s funny that Liza asked this question now, by the way, because the editor of my new book just this morning observed that I use a lot of em dashes. She knows my book is all me (she’s got the receipts for every painful draft!), but others who don’t know me might see the em dash and act like Liza’s CEO. So I’ll be taking my own advice here, on all these points.

* * *

Why do I care so much about this issue? Why not just cancel the stupid em dash forever? Why do I care so much that I launched an Em Dash Store?

Why is this the SECOND newsletter I’ve dedicated to the em dash? Here is the first.

I thought the whole Em Dash Persecution would be over by now. But… well, it’s not. Not even close. Liza and so many other writers are now living proof that this issue is STILL an issue. 

So here’s why I still care. And will always care:

I refuse to let us be bullied by AI. I refuse to let anyone—machine or individual—tell me what’s human and what’s not.

The way we take care of small things is how we take care of big things. The em dash is a small thing. But it’s one important way writers can claw back what’s ours from a technology that has—let’s be honest—already taken quite a bit from us.

We can’t push AI back into a box. But we can reclaim what’s ours.

If you’ve always used the em dash: Please continue!

If you haven’t, learn how—and why it matters. It’s not about being “correct” with grammar and language. It’s about using the tools we have to express emotion, drama, insights on the page.

AI uses em dashes. Humans use em dashes.

That does not make an em dash an AI fingerprint any more than Batman’s cape makes everyone in a bath towel Batman.

The em dash is not a tell. It is punctuation. And, used well, it does real work.

Is this a hill I want to die on?

Yes. Yes, I suppose it is.

The post Why Care About The Stupid Em Dash Anyway? appeared first on Ann Handley.

***

I spent the weekend disturbing the spider ecosystems thriving in the corners of my Tiny House Studio—a small, square office, roughly 12×12, tucked into a corner of the yard.

I’d been meaning to take care of the spider situation for a few weeks. But I was avoiding it, to be honest.

Ignoring the growing number of feathery webs, looking past the small piles of spider trash on the floor: the chewier parts of a fly, the undigested husk of a… beetle?

Gross. Spiders can be real pigs.

Then I started noticing more and more spider egg sacs—tiny cement-colored balls that look rolled out of boiled wool and dirt. Sepia-tone models of that spiky coronavirus ball we remember from 2020.

Pretty soon there would be a population explosion. Ugh. Time to sweep.

* * *

You know how you have a plan to handle one small thing (spider webs) and so you take care of that one thing and then you stop?

Me, neither.

Next thing I knew, I had all the desk squeezed to one side of the studio. Sweeping led to swabbing the floor like a dogged deckhand. Then I pulled every book off the shelves, the ones that sit behind me on Zoom calls. There are hundreds. Many by friends, many I’m quoted in. I started leafing through a few; it was like re-meeting old friends.

After three minutes I look up and I’m shocked to see that three hours has passed.

Here are some gems I rediscovered, all new or new-ish. The first two make great graduation presents!

STUPIDER PEOPLE HAVE DONE IT

Marketing Truths, Career Moves, and Life Advice for Doers

Jay Schwedelson

Why I like it: First, because it’s by Jay. I love him. I love his generosity and his fun, funny, irreverent, off-the-charts energy.

Jay and I are sometimes collaborators; he makes me a better version of myself. His book will do the same for you—because it grabs you by the shoulders and shakes you until your bones rattle around inside your skin: Hey you—stop waiting to feel qualified, this book says. Try the thing. Test the weird subject line. Make the offer.

You have one life. Laugh at yourself more, for Pete’s sake.

A passage I love: “You want to be average? Best practices will take you there. You want to be invisible? Best practices will carry you gently into the arms of mediocrity and tuck you in with a blanket labeled ‘Industry Standard.'”

P.S. Jay is donating anything he makes from the book to the V Foundation for cancer research!

WHAT DO YOU DO WITH AN IDEA? 
10th Anniversary Edition

Kobi Yamada, Mae Besom

Why I like it: I love this story of an idea and the child who helps bring it into the world. 

My friend Andrew gave me this book just a week or so ago. Unbeknownst to him, it came at the weird in-between time after I’d finished writing my new book but before anyone had read it yet. I was starting to feel the demons of doubt creep in; the fear of getting things wrong. This idea is too big. Is it dumb? Will people laugh at me?

Don’t think of it as a children’s picture book. It’s a story for anyone has ever had an idea that felt too much, too weird, or too out-there. It’s for anyone who needs encouragement to embrace the impossible. That includes me. And maybe it includes you, too.

A passage I love: “What do you do with an idea? Especially if it’s an idea that’s different, or daring, or just a little wild? Do you hide it? Walk away from it? Do you pretend it isn’t yours?”

CONTENT FOUNDATIONS

Scale your content with AI without losing your voice

Erika Heald

Why I like it: Erika’s book is for the content leader who doesn’t want generative AI to get its slick, oily hands all over their marketing.

You get frameworks, templates, and workflows up the wazoo. But it also feels like a breath of fresh air because her advice on AI adoption at scale is grounded in a sensible foundation that too many of us skip.

A sentence I love: “Most brands don’t have a brand voice problem—they have a brand voice documentation problem.”

EXCEPTIONAL EXPERIENCES

Five Luxury Levers to Elevate Every Aspect of Your Business

Neen James

Why I like it: Neen takes the principles of luxury and strips away the exclusivity and snobbery.

One time I was in the Turkish Airlines first-class airport lounge (I wasn’t paying for the flight; I’m not made of money) and as part of the lush hectare of fruit and cheese was a honey station with a live bee colony. (Live. Bees.)

THIS, I thought. THIS… is luxury.

Neen James says… uh… no, babe. That’s not quite it. Luxury is not live bees making honey in an Istanbul airport. Luxury is about making people feel seen and considered. Luxury is about being obsessed with experience.

Most “experience” advice gets fuzzy fast. Neen makes the idea practical and elegant, whether you run a car wash or a consultancy or an airport lounge.

A sentence I love: “Luxury is about experiences, not things.”

* * *

And a few honorable mentions:

HUMAN-CENTERED MARKETING

Ashley Faus

Ashley argues for marketing that meets people as people—with context, curiosity, room for complexity. She asks us to think less like funnel managers and more like playground designers: people can move up, down, sideways, around, and back again; they can use the content “wrong.”

PERSONAL BRANDING FOR INTROVERTS

Goldie Chan

You don’t have to be the jazz-hands clowniest or loudest person in the room to be easy to connect with.

DON’T CALL IT ART

Austin Kleon

Unlearn what you’ve learned. Give yourself permission to be terrible, and treat yourself with the care of a loving parent so the wild 4-year-old in you will come out and play.

* * *

Back at my Tiny House Studio, things are clean and spider-free. It makes me happy every morning, when I throw open the windows, to be truly alone and with no creepy cement balls lurking in the corner, waiting to explode like grotesque little undulating time bombs.

It was only later that I thought of the obvious metaphor: cleaning out the cobwebs. Reclaiming a space.

The satisfaction of doing the clearing yourself. Of finishing your own unfinished business. Of giving yourself a fresh perspective.

A good book does that, too.

A good book sweeps a corner of your brain. Clears out a stale assumption. Disturbs the ecosystem of old ideas you’ve been letting accumulate rent-free.

Truly a gift.

SPEAKING OF NEW BOOKS!

I was blown away by all the love for my new book, ASAP: As SLOW As Possible, coming February 2027.

If you missed the announcement, get on board, babe:

>>> New book announcement here. <<<

More details are coming in the next few weeks: the cover, the pre-pub giveaways, whatever ridiculous shenanigans I can think of between now and then.

But for now, mostly I just want to say Thank You.

It’s scary to share your ideas with the world. (Is this dumb? Will people laugh? Did I get it wrong? Will anyone care?)

Even after three books, I still feel that nervousness. Actually, especially after three books.

Thank you for meeting this one with such kindness. You give me courage.

The post 7 New-ish Books I Love (Including 2 Special Ones) appeared first on Ann Handley.

***

My left eyelid has been twitching for the past month or so.

It’s a quick, intermittent fluttering, like my eyelid is trying to send me distress signals in Morse code.

“We haven’t been getting enough sleep,” my eyelid taps out.

“ABORT. We are sTreSS*d,” it taps.

“You are currently 97% coffee,” it warns. “R U ok?”

Which is my way of explaining my absence here these past few weeks: I have been heads down and frantically grasping every moment I have to finish up the final draft of this infuriating my delightful new book.

A few weeks ago I found out that its deadline was not—”I repeat NOT,” Eye Twitch shouts—the end of June, as sweet, clueless me had been thinking back in April when I was happy and young and innocent.

Instead, the deadline was cold-splash-of-water-May 15. A full 40 days and 40 nights earlier than I expected.

You can do a lot in 40 days and 40 nights.

You can survive a flood in Noah’s Ark. Wait for Moses to come down from Mount Sinai. Endure a quarantine. Procrastinate doing actual work by researching how the word quarantine comes from the Italian quaranta giorni—literally 40 days—the isolation period for ships during plague-era Venice. Should I rabbit-hole research a Venice trip…?

For me, the 40 days/40 nights was a hyper-frantic, self-quarantined final push to the deadline. At the end, I died fully dead. I did not rise again three days later. It took a few weeks.

But I buried the lead—the deadline! I hit it! Please clap!

The draft is done. Eyelid Twitch lingers. It’s called eyelid myokymia, by the way: a mild, involuntary spasm of the upper eyelid muscle. It typically resolves on its own, unlike the brain aneurysm I had naturally presumed it was.

* * *

My new book is called ASAP (As SLOW As Possible): When to Take the Long Road in a Shortcut World.

What’s it about?

It’s about you and me, living in a hyper-optimized time that keeps mistaking faster for better.

It’s about knowing when speed serves us—and when slowing down is the smarter, stronger move.

It rebels against the false urgency baked into modern work and life. It asks: When is speed useful? And when does the shortcut undermine us… and cost us our judgment, creativity, relationships, work, or lives?

Because when everyone has access to the same shortcuts, the real edge is knowing when not to take them.

It’s got brain science. Storytelling. Real people who’ve chosen the long road when it matters—with astounding results. Six Slowments. One framework. A way to know when a moment deserves more of you.

And (because it’s from me) humor and wit and the occasional em dash. (Because JUSTICE FOR EM DASHES!)

It’s not boring. It’s not moralistic: I don’t want us to do less, opt out, or become the kind of people who ferment things in sheds.

Instead, I’m inviting us to get better at knowing when speed helps—and when it hollows out the very things that make us feel alive.

The new book is from Penguin Random House, a new publisher for me. It’s out February 2027, because that’s how Big Five publishing works. (More on this later, maybe, if you’re interested.)

So that’s what I’ve been up to. And that’s why I’ve been absent from writing to you.

Many of you reached out—in unknowing solidarity with Eye Twitch—asking some version of: R U OK?

Where you been? you asked. Some of you actually resubscribed with a different email address—thinking the problem was them… not me. 🫣

I appreciate you. I’ve missed writing to you. I’ve missed you.

I’m glad to be back.

* * *

The marketer in me wonders whether I should introduce the book by name at all.

Maybe I should keep it vague, I think. Say I’ve been “busy.” Blame “Maycember.” Make some hand-wavy references to “a big project.” Yadda yadda.

Maybe I shouldn’t say anything until I have an actual call to action: a book landing page, a cover, a preorder link, a backstage pass to the writing process, intel on what it’s like to publish with Penguin Random House after doing things so differently in the past.

Maybe I should wait until I could offer you fun book-launch treats or preorder bonuses or a form to invite me to speak at a special discount book-promotion rate. Or, or, or.

Marketing, you know. That’s how it works.

Eye Twitch talked sense into me.

“Listen up,” Eye Twitch said. “You owe your newsletter readers—the people who show up for this letter, week after week—a real and honest explanation.”

“You are being silly,” Eye Twitch continued. “You do not have to Jazz Hands this book with your own people.

“This book is your best work. It’s fun. It’s funny. It’s YOU. It’s a fresh take on a modern problem: We already know how to go fast. What nobody taught us is when not to.”

That Eye Twitch may be only a month old, but dayum… it’s wise for its age.

At some point, I will ask for your help: to join a prelaunch team, to preorder, to share, to tell a friend, to invite me to speak to your group, to send a cold eye mask to soothe Eye Twitch.

At some point, I’ll need your support.

For now, I just wanted to say: I’m back. Thank you for still being here.

The post Sorry for Ghosting: Where I’ve Been (Pssst New Book!) appeared first on Ann Handley.

***

This week I was at the National Agri-Marketing Association in St. Louis, Missouri, where I gave a brand-new speech on how we prove the power of a slower, lasting marketing move. (Waves to new NAMA friends!)

The night before the speech, I was in my hotel room. I had just drifted off to sleep when suddenly the WOOP-WOOP-WOOP of a police siren went off a foot from my head. Like my bed was being pulled over for speeding.

Which was confusing. Until I realized the siren was actually an emergency alert alarm sounding on my phone:

TORNADO WARNING!!!
TAKE SHELTER NOW IN A BASEMENT OR INTERIOR ROOM!!!
PROTECT YOURSELF FROM FLYING DEBRIS!!!

Up until this week, my entire knowledge of tornadoes was through my annual viewing as a child of The Wizard of Oz. So in my dumb, sleepy stupor I thought: How bad could it be…? No hotel alarms sounding. No knock on the door.

And: Would it really be so bad to be transported somewhere wild and colorful and cinematic—like Munchkinland?

Anyone who has actual lived experience with tornadoes would not be so cavalier. But here I was… a rookie weighing the pros (take shelter) and cons (stay put).

PRO: THAT SIREN
CON: But I’m in my pajamas.

PRO: YOU ARE ON THE 19th FLOOR
CON: But I’m tucked under the covers with my glasses off.

PRO: YOU COULD DIE
CON: But… it’s a steel and reinforced-concrete building?

I put it to an internal vote of my (sleepy) brain and (snug) body: We decided we were comfortable. We voted to stay put. We voted Munchkinland.

Also, you should know that in a fight-or-flight emergency, my nervous system chooses a secret third path: duvet.

Which obviously leads us to email marketing.

The power of email hasn’t changed. But the weather around it has.

The New Email Climate

Quick history lesson (because facts are important. Did you know that it’s a myth that tornadoes usually bypass cities because of city heat?):

A lifetime ago—27 years!—Seth Godin published his seminal book Permission Marketing. That same year, my company, ClickZ—among the first serious digital marketing publications—held one of the first email marketing conferences ever.

Seth defined permission marketing as the privilege of delivering “anticipated, personal and relevant” messages to people who actually want them.

It sounds basic now. But in 1999, it was a siren going off on the nightstand of every marketer.

Permission used to be enough. If someone subscribed, that itself was valuable because it gave you direct access to their attention. Especially in a world where an inbox got roughly four emails a day.

That’s no longer true. Today, most of us live in our inboxes. 

When AI Manages the Inbox

Stroll with me into the very near future… a world where inboxes have a new AI robot in charge.

In this new land—a kind of Automaton Munchkinland—we don’t live in the inbox anymore. Maybe we barely check the inbox at all.

Instead, messages are filtered, summarized, collapsed, prioritized, pasteurized, pulverized, and possibly purified. All before a human ever sees them. A human is summoned only according to certain set parameters.

The path looks like this:

For marketing, that means permission doesn’t guarantee visibility anymore.

Deliverability does not guarantee it, either. It’s not enough to make sure all your T’s are crossed and I’s are dotted so you land in the primary inbox, high-fiving all the other emails who’ve dropped in alongside you. YOU MADE IT is no longer the goal.

And that raises an uncomfortable—but important—question:

So what happens to email marketing? Are we dead in the path of this storm?

No. St. Louis hasn’t been hit with a tornado in years, right?

But the sirens are going off.

The Sirens Are Sounding

The new goal is neither access nor deliverability. It’s being consciously and expressly chosen.

It’s a person manually selecting your shiny, fresh email and telling the robot: Yo. Save those for me.

Your relationship with the recipient is the difference between being seen… and being skipped.

For years, we optimized for deliverability—how to get in. Now we need to optimize for selection—how to be chosen.

The old way vs. the new way:

Visibility is now based solely on value. They choose to read you.

Email is still the GOAT—but the advantage is no longer email itself. It’s what email enables when it’s chosen.

And that asks us to shift our thinking:

From messaging → making meaning
From broadcasting messages → corresponding with people
From scale first → story first

Marketing needs to show up differently:

• Individual personality over brand. People choose people, not logos. Your quirks are the signal through the noise.
• The From line matters more than the Subject line, because the storyteller is the new correspondent. Make your newsletter from a person. More than that: Make it sound like it is.
• Humanity over polish. The perfectly crisp email sans fingerprints is forgettable.
• Fewer messages with clearer intent. Every send should have a reason to exist. If you can’t name it, neither can your reader. (We talked specifics on that here.)
• Work that earns selection—not just work that clears the hurdle of the spam filter.

Pro tip: Pull up your last three email sends. Look yourself square in the eye and answer this question with unflinching honesty: If an AI assistant were triage-reading these emails in an inbox, would it flag this for my reader? Would the reader think… Nay, nay. This one is for me? Is the work genuinely worth their time? That, my friend, is our new bar.

• A voice your readers would genuinely miss. Would they miss your emails if you stopped sending them? (Try it.)
• Specificity that feels unmistakably you. Anyone can write about the storm. Only the person who lived it can write about choosing Munchkinland from under a hotel duvet.
• A perspective no summary bot could give. If an AI could have written it, an AI will summarize it and your reader will never see it.

It’s weird to realize that the inbox you’re delivering to isn’t the inbox your reader actually reads. There’s a layer between you and them. And that layer is making ***decisions.***

But that’s the world we now live in.

The Storm Is 5 Miles Away

In St. Louis, the storm passed 5 miles outside the city. Right now, the storm is 5 miles away for email, too. 

You still have time to act. Do not pull the covers over your head. Do not be sleepy me in my bed.

What changed isn’t really email; it’s actually attention. Attention has always been scarce, and now it’s also curated. The algorithm that rules your social feeds is also in the inbox.

I’ve heard smart folks like Dan Oshinsky at Inbox Collective and the team at Litmus talking about this for a while now. It’s getting more urgent.

The only email strategy that actually works from here on out is being someone your reader would genuinely miss if you stopped showing up.

That’s a relationship problem, a writing challenge, and—if you’re willing to invest the time—an opportunity.

When speed becomes cheap, judgment carries a premium. That’s true in marketing strategy. It’s true in content. And it is especially true in email.

Also it’s true of tornadoes.

It turns out St. Louis was hit with a tornado less than a year ago, in May of 2025. Yikes.

This week, it might’ve bypassed the city completely. I was able to pretend it wasn’t happening. 

Next time, I might not be so lucky.

The post Email Is Dead, Long Live Email  appeared first on Ann Handley.

***

How do I write in a more engaging tone? How do I develop a voice? How do I stand out when AI can produce competent prose faster than it takes for you to get to the end of this sentence?

I got versions of all of these questions in my inbox over the past few weeks. To find out, we’re visiting a federal courthouse in Washington, DC.

Let’s belly up to the bar.

* * *

Exhibit A:

“The President of the United States is the steward of the White House for future generations of First Families. He is not, however, the owner!” —US District Judge Richard Leon, ruling this week to halt construction of Trump’s White House ballroom

Right away, what do you notice? The exclamation point, right?

There are 18 of them in a single ruling. EIGHTEEN!!!

Judge Leon—a George W. Bush appointee, let the record show—is famous in legal circles for his punctuation. He used 26 exclamation points in an opinion last year blocking an executive order targeting the law firm WilmerHale. That ruling also included a gumbo recipe in a footnote. (It seems like I’m making up this recipe thing. I am not making it up.)

I saw his punctuation proclivity mentioned in a few places this week. But nobody interrogated it.

Court is now in session.

* * *

Legal writing is one of the most ruthlessly shackled genres in existence. The passive voice, the bloodless construction, the deliberately neutralized tone. It is hereby ordered. The court finds.

Wide, jaw-cracking yawn. Legal writing veers into dullness like someone falling asleep at the wheel.

And yet I present as counter-evidence: Judge Leon, clearly feeling things and seeing no reason to pretend otherwise.

So. How do we write funnier? Develop a voice? Stand out?

The court calls its next witness… Generative AI, please take the stand!

The robot glides forward like a literate Roomba, bumping noisily up the stairs and into the witness box.

(There’s a brief procedural snag when the bailiff holds out a Bible for the oath and realizes there are no hands.)

AI clears its nonexistent throat:

“I would edit Leon’s rulings into oblivion,” it confesses. “I would sand off the exclamation points. Cut the gumbo recipe.” A nervous glance at the jury.

“I would produce something perfectly serviceable, utterly professional, and completely forgettable.”

Low murmurs ripple through the gallery. A few boos rise from the back row.

Sustained.

* * *

The very things that make Judge Leon’s writing memorable are exactly what a large language model would flag as unprofessional and scrub them out. AI prose can’t violate expectation because it is expectation. It’s the average of everything. There’s nothing to bump up against.

Humor that makes a reader snort at their desk requires a self. A consistent enough presence that the reader can feel when you depart from it.

That’s why Judge Leon’s exclamation points are funny: You expect a black-robed judge in a dead-serious tone like he’s peering over his half-glasses at you. Instead, you get a guy who’s absolutely had it.

The violation of that protocol has to feel intentional, not accidental. Unintentional weirdness is just confusing. Intentional weirdness is earned. It signals a mind at work—which is what makes it delightful rather than disorienting.

Judge Leon doesn’t accidentally deploy 18 exclamation points and a stew recipe. He knows exactly what he’s doing. The exasperation is real, but the performance of it is deliberate—a wink at the reader, a sense of the person writing the words connecting with the person reading them.

The court calls it: That’s judgment.

* * *

When speed becomes cheap, judgment carries a premium.

AI can produce competent prose in seconds.

What it cannot do is read a situation, weigh it, feel it, and leave evidence of that process on the page.

It cannot be the exclamation point in Judge Leon’s literal judgment that says: I assessed this! I found it worthy of indignation! Here is my ruling! Try the gumbo!

That’s the whole job for writers now. Not information. Not even personality, exactly. Something greater:

Evidence of a mind behind the work.

So the path to standing out has never been more clear:

Stop editing yourself into acceptability. Stop covering up how your mind works.

* * *

So where does that leave us?

 VERDICT 1: Punctuation is a voice choice, not a grammar rule.

Most of us were trained to distrust the exclamation point—at worst, to hate its cheery, unhinged energy. The writer Elmore Leonard famously said never use one. Or else. (Elmore didn’t even add one exclamation point to that subtle threat. Bold.)

Judge Leon says pfft to Elmore and all that.

The lesson isn’t “use more exclamation points.” It’s that every punctuation choice is a voice choice. (Rejoice!) (Sorry, couldn’t help it.)

 VERDICT 2: Feel the feels.

Professional writing norms push a neutral, balanced, measured tone. But readers feel something when a writer clearly feels something.

 VERDICT 3: Constraints are powerful.

Leon operates inside one of the most formal, formatted genres in existence. His exclamation points pop because of the surrounding formality. Know the conventions of your genre so you can break them.

 VERDICT 4: A consistent quirk becomes a signature.

One exclamation point is a blip. Eighteen is a style. Commit fully to your weirdness. Do not lock yourself inside the prison of acceptability!

One more thing:

 VERDICT 5: AI can extend your voice. It can’t invent it.

AI can help you build on what’s there. It can’t discover what makes you, you.

And honestly: would you want it to discover your weird for you? The fun is finding it yourself.

* * *

THE DISSENTING OPINION

A voice from the gallery pipes up: “But a judge can’t get fired!”

The court acknowledges the outburst. Bailiff, let them speak.

I hear you. Judge Leon has a job for life.

No performance review. No brand guidelines. No VP of Marketing who has Opinions and Thoughts about exclamation points or puns or whatever. Judge Leon can afford to be flamboyant in a way some of us can’t.

But here’s where I’d push back.

You don’t need to be Judge Leon, out there burning through legal-speak with a flaming punctuation mark.

You need to find the smallest version of that impulse your context will allow—and then commit to it consistently until it becomes the thing people recognize as yours.

A word you choose. A punctuation tic. A structural habit. Oddball metaphors. Some quirk that, over time, becomes a signature.

Judge Leon didn’t start with 18 exclamation points. He started with one. Over time, it became his signature.

* * *

What is yours? And where is that line for you?

You know what I’m going to say, don’t you…

You be the judge.

The post What AI Would Delete From Great Writing appeared first on Ann Handley.

The tension you’re describing isn’t really about the newsletter. It’s about two wildly different definitions of what’s “working” in your marketing.

The Sales Manager is measuring with leads as the metric.

You’re measuring with trust as the metric.

Neither of you is wrong. But you’re not having the same conversation. It’s the old blind-men-and-the-elephant problem: One of you has hold of the trunk, the other the tail, another an ear… and so on. Each is adamant they’ve got the whole story.

A few thoughts for you and the Sales Manager, who in my head I’ve now named Steve. (For no reason other than he seems like a Steve.)

Start with the newsletter’s actual job. A newsletter is like a border collie: It needs a job or it’s just racing around your strategy deck, barking at random metrics.

Its job is not to say, “We cover fintech.” Its job is to help one specific reader think through a specific kind of problem.

So in financial services technology, step away from the broad topic bucket:

NOT THIS: payments, platforms, the magic and wonders of fintech

YES THIS: feelings—meaning the anxiety, decision, or ambition your reader carries into work on a regular Tuesday

Maybe that’s:

• What keeps them up the night before a board meeting
• What decision they’re worried about getting wrong
• What pressure lands on their shoulders every quarter

Step into their shoes. Slip on their skin. Feel what they feel. (You toss the border collie a biscuit. He spins with joy.)

The goal is that tiny electric moment when a reader pumps their fist in the air and screams inside their head: YES. This is exactly how it feels for me.

And the more precisely you write to someone, the more the wrong someones opt out. Godspeed, Wrong-someones. Self-selection is good in B2B Marketing.

(Quick aside on unsubscribes, because marketers can get weirdly tender about them—and I used to, too: Let them leave. It’s better they leave than linger on your list like zombies—dead-eyed, shambling around, clicking nothing, wanting nothing. Not everyone is your person. That’s perfectly fine.)

Back to Steve.

Steve wants enterprise buyers. Fair enough, Steve.

But here’s the secret about the magical and elusive unicorn called the enterprise buyer: They rarely convert cold from bottom-funnel content.

They research slowly. They trust slowly. They buy slowly. A newsletter that builds familiarity over six months is doing work that a cold demo offer simply won’t get the chance to do.

So what’s missing here isn’t the newsletter. It’s the explicit connection between what the newsletter builds—trust, familiarity, credibility—and what the business eventually wants: pipeline.

Which means that if you want the newsletter to pull real strategic weight as it herds prospects like a border collie all over the internet… you need two things:

1. A clearer editorial through-line—a point of view readers come to associate with your brand
2. A better picture of who is reading—not just how many

Because 3,000 readers who are CFOs at mid-market companies is an entirely different asset than 30,000 random LinkedIn subscribers.

The newsletter isn’t the problem.

You and Steve both need the patience to let that connection materialize.

Related: Should You Publish a LinkedIn Newsletter or a Traditional Newsletter? Or both?

The post Is content ‘working’ if it’s not delivering obvious leads? appeared first on Ann Handley.

***

Dearest Gentle Reader:

It has come to this author’s attention that certain members of our industrious professional class have questions.

So this week, I will answer your letters—dispensing counsel on writing, dealing with nincompoops & nincom-bots, and sharing a tale as old as a dowager: the tension between humanity and AI.

In other words, I’ve just finished the new season of Bridgerton. You likely sensed this already, did you not?

I’ll resist the urge to write this entire newsletter in the tone of a Regency-era scandal sheet.

But kindly imagine me writing this with quill scratching across parchment, seated at a too-small desk while wearing a dress engineered to restrict both oxygen and female ambition.

Without further ado…

* * *

With so much AI-assisted content out there now, what do you think is the one human element in writing that still makes someone stop scrolling and actually feel something? —Amanda

Not sure there’s only one thing. But for me it’s probably this: specificity of observation.

A detail that’s yours—neither generic nor general. One particular person paying close attention in one particular moment—then holding it out like an outstretched hand: This is how it feels for me. You too? (To paraphrase the great Kazuo Ishiguro.)

The goal of everything we write is to make someone think: So it’s not just me.

Specific enough to be true. True enough to be universal.

I talk about this a lot in Everybody Writes 2, BTW.

* * *

I’ve been using AI tools more and more at work, and at first it felt kind of fun, or like a superpower. But lately I just feel buried. Like I’m doing more than ever but somehow never caught up. Is this just me adjusting, or what? —Simone

A short and declarative sentence: It’s not just you.

We’ve seen this before. Every time a tool promises relief, it somehow ends up raising the bar.

Email was supposed to streamline communication—and ended up being our whole job.

Smartphones were supposed to untether us from the desk—but now we are never untethered at all.

Slack was supposed to lift the burden of email—and now we are (ping!) immediately (ping!) accessible (ping!) all day long.

Even outside of work:

Streaming was supposed to free us from rigid TV schedules—and now we spend 20 minutes deciding what to watch.

Each one delivered on its promise—and then hot-glued a larger obligation to it.

Now in waltzes AI, promising to give us time back. But what’s actually happening is that AI seems to be intensifying work.

Last week I saw some new research that tracked how generative AI changed work habits at a real company over eight months. (Pause to underscore: Actual people. An actual workplace. Not vibes. But lived experience.) It was published in Harvard Business Review.

The researchers found something remarkable. Or maybe striking is a better word:

AI didn’t reduce work. It intensified it.

People moved faster. Took on a broader scope of work. Let that work seep into hours that used to be off-limits. They multitasked like crazy.

Product managers and designers writing code. Researchers taking on engineering tasks. Individuals across the org doing work they would have previously outsourced, deferred, or avoided entirely.

All because AI made “doing more” feel possible—enjoyable, even. And empowering! Right up until… suddenly, it wasn’t.

That “workload creep” is the oldest story in the productivity playbook—now wearing a new gown from the modiste.

It’s not just that work spilled into our off hours.

It’s that the definition of what one person can attempt expanded like Sea-Monkeys the moment you add water.

The tool is always there. Always on. Always easy-peasy-lemon-squeezy frictionless.

Yet frictionless, it turns out, is not the same thing as easier. It’s not the same as relief.

Which is why I suggested a few weeks ago that AI might benefit from slower, more considered adoption. Not to resist the technology—but to give ourselves time to decide what work is actually worth expanding.

Efficient is not the same as effective.

So no, Simone: you’re not merely adjusting. I think we are all experiencing something profound and structural.

The question isn’t whether AI is useful. It clearly is.

The question is whether you are shaping how you use it—or whether it’s shaping you instead.

Something tells me that may become the defining workplace question of this decade.

The post Why ‘Helpful’ AI Tools Make Us Busier Still appeared first on Ann Handley.

***

Maybe you, like me, read Matt Shumer’s mega-viral piece about AI eliminating 50% of white-collar jobs in the next 1-5 years, and maybe you, like me, thought… Oh. Isht.

It’s well-crafted, detailed, and structured to make you feel like you’re getting the inside scoop from someone who knows. And everyone else is sleepwalking into disaster.

It’s also designed to trigger panic.

I did panic at first. And then I didn’t. So I wrote this in case it helps you, too.

Something Messy Is Happening: On AI, Panic, and Asking Better Questions

* * *

I published that ^^ last week on LinkedIn. My rebuttal went a little bananas, with 2,200 reactions and 500+ comments. If you haven’t seen it, please go read it.

It’s important—not because I wrote it, but because it runs counter to the @dApT oR dIe!!! narrative that is literally everywhere right now.

The heart of my rebuttal to the panic-driven pandemonium is this:

When speed becomes cheap, judgment carries a premium.

AI is making speed cheap—but the best response is not to move faster. The better, saner response is to slow down enough to ask better questions:

What am I actually trying to make or do?
What’s worth protecting because it compounds over time?
Where does friction create value instead of destroying it?
What work do I love doing, regardless of whether AI could do it faster?

That’s the gist of my rebuttal to Matt’s argument, among other nuances.

And for no reason at all, I’ll mention here that Matt has an AI technology to sell, and I do not.

* * *

But what if “slow down” feels like advice you can’t afford?

After I wrote that, conversations elsewhere made me question myself: Is that even fair advice?

Is slowing down itself a privilege? I wondered.

What if you don’t have runway—a decade of work behind you, people to vouch for you, relationships you can rely on, a financial cushion to be deliberate?

For some people being disrupted right now, the timeline isn’t a mindset choice. It’s an economic reality they’re already living inside.

So… is that fair advice?

Yes. It is. (I thought about this for days and days. Not just for three paragraphs.)

Here’s the deal: Those with the least margin for error are the ones who can least afford panic… I’d argue it’s more important then to take a beat.

When pressure spikes and stakes feel high, we tend to make reactive moves. We grab whatever feels safe right now. We abandon what we’ve already built or are building—skills, reputation, relationships, domain expertise—because the noise around us is so loud that staying the course feels like you’re swimming in a Swamp of Denial.

The “move faster or die” message does something sinister: It makes every pause feel like falling behind. And when you’re scared, that feeling is almost unbearable. Inaction feels like error.

Here’s the truth, in marketing and in life: Reactive pivots are expensive. Bets made under pressure are often costly—in time, money, and the compounding cost of starting over.

The people with the most runway can absorb a wrong move. The people without it… can’t.

* * *

When I say in my original post “don’t let someone else’s timeline determine how you spend your life,” I’m not saying slow down as a luxury.

I’m saying: “Be deliberate, especially when you can’t afford not to be. This is important. Your next move counts.”

Here’s what I’ve seen work—not just for senior folks, but for people at every level navigating the disruption.

• Own something that gets better the more you do it. Not a title. Not a tool.

Own a capability that compounds—one AI can assist but not originate.

You don’t need decades. You already have context, taste, pattern recognition. Develop that deliberately.

Make it unmistakably yours.

If you’re not sure what that is, that’s the question worth slowing down to answer.

• If you use AI, use it in service of your expertise—not as a substitute for it. (And if you decide it doesn’t belong in a piece of work right now… well, that’s a choice, too.)

The most resilient people I’m seeing aren’t the ones who’ve mastered the most tools or the Perfect Prompt™. They’re the ones who’ve figured out how AI makes their particular expertise more valuable—more scalable, more accessible, more fun to work in.

Tools should extend your judgment. Not replace it.

• And for the love of Matt… resist the urgency! I don’t think the AI Apocalypse is imminent. (I explain why in my LinkedIn post.)

And yetttttt… there’s a whole economy built on making you feel behind: courses; certifications; “experts” who popped up like mushrooms overnight, pivoting from selling Metaverse real estate to AI “consulting.”

LinkedIn posts that implicitly suggest if you’re not moving fast enough, you’re already losing; guys on social media who say things like COMMENT I WANT IN to get their Agentic AI guide.

Some of it is helpful. Much of it is not. Much of it is noise that benefits the people selling the urgency… not the people feeling it.

* * *

I know slowing down to ask “what am I actually good at” and “how do I own a thing in this new world?” when you’re under real financial pressure feels… like not enough? But it is.

Even a short, intentional pause—a few days of honest assessment moving through a situation before the next move—is always worth it. It’s a way to invest in yourself.

Not slowness for its own sake. But for the sake of deliberate speed: knowing what you’re running toward, and why, before you start running.

* * *

When I was a kid, I was obsessed with the Little House on the Prairie books. I rode my bike around my suburban neighborhood, pretending it was a horse and the banana-seat a saddle. I started calling my parents “Ma” and “Pa.”

Laura Ingalls Wilder tells a story, in a later book, about a neighbor who spent hours every day hauling water to his homestead. Back and forth he went with his horse-drawn wagon, hauling water barrels from the creek.

Someone asked why he didn’t just dig a well on his property instead of spending all that time hauling water. “I would,” he said. “But I can’t find the time.”

I think Matt and the panic folks are telling you to keep hauling water—except now they’re telling you to swap your wagon for a monster truck.

I’m saying: It’s time to dig your well.

The post When ‘Slow Down’ Feels Like Advice You Can’t Afford appeared first on Ann Handley.

It’s well-crafted, detailed, and structured to make you feel like you’re getting the inside scoop from someone who knows. (And that everyone else is sleepwalking into disaster.)

It’s also designed to make you panic.

I’m here to say: Do not panic. Let’s talk about it.

First things first: I’m not dismissing AI. I use AI. I think the technology is remarkable. It will continue to improve—of course it will. Matt is right about a few things, including that most people underestimate how much has changed in the past year.

But at the same time… he’s not right about everything. And he’s asking the wrong questions. The questions you ask determine the life you build.

The COVID Trap

Matt opens by comparing February 2026 to February 2020—remember when you thought people were overreacting about a virus? And then the world shut down?

In some ways, it’s an incredible analogy (I love a good analogy), effective because it’s a gut-punch that triggers a visceral feeling inside us all: I don’t want to be the person who dismissed the warning signs again.

But if you think more about it, it’s a terrible analogy.

COVID works on the surface as a comparison because, yeah, it was a once-in-a-century event. Global pandemics that shut down the entire world almost never happen. It surprised and shocked everyone.

“This AI moment is as rare and catastrophic as a global pandemic,” is what Matt says.

Okay. But let’s unpack it a little more….

COVID had a clear, measurable, physical mechanism. Virus spreads. People got sick. Hospitals overflowed and set up sick bays in their parking lots. Governments shut things down. Restaurants set up tables outside in freezing weather; we ate pasta carbonara with gloves on. We hoarded toilet paper and hand sanitizer. You could see it happening in real time, country by country.

AI job displacement is much murkier. When does it “happen”? When the technology is capable? When companies adopt it? When people actually lose jobs? Those are very different timelines, aren’t they? Matt mashes them all together into one formless blob and plops them out onto a Panic Conveyor Belt.

He’s saying: “The technology can do the work now… ergo, the jobs are gone!”

But that skips about five major steps of economic and social change.

But Capitalism

But capitalism will force adoption, you might think. In other words: companies will adopt AI to save money, creating competitive pressure that forces everyone else to follow or whither away.

But that assumes “cheaper and faster” always wins. That’s not actually true—especially not in knowledge work where trust, relationships, and stakes matter.

COVID spread because you can’t choose not to be exposed to a virus. AI adoption spreads only if companies choose it. And that choice is complicated. (More on that in a sec.)

The Race Nobody Asked to Run

Matt’s entire argument rests on one assumption: AI can do it faster and better, therefore it wins. It’s a refrain we hear from a lot of AI companies.

DEEP SIGH.

It’s the same logic as the AI book-mill romance “writer” profiled in the NY Times recently who asked:

“If I can generate a book in a day and you need six months to write one, who’s going to win the race?”

Matt is also asking: Who’s going to win the race? The answer for both the AI book-mill operator and Matt is, of course, AI. The robot wins. ROBOTS ALWAYS WIN!

But I keep coming back to: What race? Who said we’re racing? What are we racing toward?

Matt’s piece is saturated with racing language: “get ahead,” “head start,” “falling behind,” “the people who will struggle most are the ones who refuse to engage.”

The entire framing assumes speed is the only metric that matters. That faster is always better. That if you’re not optimizing for velocity, you’re losing.

I could not disagree more with this worldview.

What Gets Lost

Here’s what’s absent from Matt’s piece:

• Any question about what work is actually worth doing, and why.
• Any acknowledgment that some friction creates value rather than destroying it.
• Any consideration that the things that take time might take time for a reason.
• Any curiosity about what we lose when we optimize purely for speed and efficiency.

He writes: “Have no ego about it. The managing partner at that law firm isn’t too proud to spend hours a day with AI.”

But what if it’s not about ego? What if some kinds of work require the time because that’s where the judgment gets built?

Matt thinks a managing partner at a law firm is valuable because she can research case law faster or draft briefs more efficiently. But that’s not actually why clients hire her, is it?

They hire her because she knows which judge will respond to which argument. Because she can read a room. Because when things go sideways, she knows who to call. Because she’s been practicing for 30 years and has judgment that comes from making mistakes and living with consequences. Because clients trust her.

AI can research the law. It can’t sign the filing. It can’t go to court. It can’t absorb the malpractice liability. It can’t build a relationship over a decade.

What About Marketers?

That’s law. But what about marketers? Matt’s argument would say that a senior marketer is valuable because he can write copy faster or analyze campaign data more efficiently. But that’s not actually why companies hire him.

Companies hire him because he knows which message will land with which audience. Because he can feel when a campaign is off before the data proves it. Because when a launch goes sideways, he knows how to salvage it. Because he’s run enough campaigns to know the difference between a metric that matters and a dumb vanity number. Because he understands the customer in ways that don’t show up in a brief. Because he knows how to lead a team.

AI can’t sit in the room when the CEO wants to pivot the entire strategy three weeks before launch. It can’t rebuild trust with a customer after a PR crisis. It can’t read the culture and know that this is the wrong time to be clever. It can’t take accountability when the campaign fails. It can’t lead that team.

Those aren’t small details, friends. They are structural foundations.

One more example: this time a personal one.

I just spent almost 2 years writing a book. Was it inefficient? “Yes,” Matt would say. “AI can do it faster.”

Listen: You are wrong, my friend. It was efficient. Because I was doing the work of figuring out what I actually think and how to help a reader and say it in a way that could come only from me. The friction between idea and expression, between intention and execution is not frivolous. That’s where the thinking happens.

Matt would say: “But AI can help you think faster.”

Mmm. Maybe.

Or maybe it helps you skip the thinking and arrive at answers that sound right but haven’t been tested against the resistance of actually working through them.

See the issue?

The Timeline Shell Game

One more thing: Matt is absolutely certain about timelines. “1-5 years.” “By the end of this year.” “Doubling every 7 months, accelerating to 4 months.”

It all sounds very scientific. Very data-driven. You nod along as you read. You feel the panic rise.

Here’s what he mentions but doesn’t fully reckon with: he runs an AI company and invests in AI startups. He discloses this upfront, to his credit. But he doesn’t seem to acknowledge how profoundly his financial and psychological incentives shape his certainty that the revolution is happening right now.

The people who were closest to crypto in 2021 were absolutely certain it would replace the financial system.

The people closest to VR in 2016 were certain we’d all be working in the metaverse by now.

Proximity creates conviction. I kept whispering that to myself all the way through the reading of it.

Matt writes like the exponential curve is guaranteed to continue at exactly this pace. But these curves always hit walls— not because of technological limits, but because real-world adoption is messy and human-shaped. Things like regulation, litigation, integration costs, resistance to change, and the fact that humans are messy and uneven and irrational and are wired a certain way.

The gap between “this works in a demo” and “this has replaced 50% of jobs” is as enormous as an ocean. And Matt hops over it like it’s a puddle.

What I Think Is Actually True

Some jobs will disappear entirely. Many more will be transformed—you’ll do the same role but with AI handling parts of it.

Each of us will face a “learn this or become less valuable” moment.

The timeline will be longer than 2-5 years. How long? No one knows (harder still to know when you’re inside the bubble.) And the change will be partial and uneven, not the clean apocalypse Matt describes.

No one actually knows anything. We are all guessing.

Except there is one thing I am certain about:

When speed becomes cheap, judgment carries a premium.

Matt is right that AI is making speed cheap. He’s wrong that the only response is to move faster.

Sometimes the right response to acceleration is to slow down enough to ask better questions:

• What am I actually trying to make?
• What’s worth protecting because it compounds over time?
• Where does friction create value instead of destroying it?
• What work do I love doing, regardless of whether AI could do it faster?

The Choice Matt Doesn’t Offer

Matt presents a binary: adapt or die. Use AI aggressively or get left behind.

But that’s a ridiculous choice.

You can use AI as a tool and still protect the friction that creates value.

You can learn what it’s good at and maintain clarity about what you’re trying to make and why.

You can take the capabilities seriously and reject the panic.

The real danger isn’t AI. It’s letting someone else’s timeline and someone else’s definition of winning determine how you spend your life.

What I’m Not Saying

I’m not saying ignore AI. I’m not saying it won’t change things. I’m not saying Matt is wrong about capabilities.

I’m saying: DO NOT LET PANIC DRIVE YOUR DECISIONS.

(I put that in ALL CAPS. Because it’s important.)

Don’t restructure your entire life around predictions from someone who has strong incentives to believe the revolution is coming right now.

Don’t abandon the work that takes time just because something else can be done faster.

And for Pete’s sake, don’t accept “who’s going to win the race?” as the only question worth asking.

A Different Question

Matt ends his piece: “The future is already here. It just hasn’t knocked on your door yet. It’s about to.”

I’ll end with this:

The future is always arriving. The question is: what are you building that’s worth the time it takes?

The post Something Messy Is Happening: On AI, Panic, and Asking Better Questions appeared first on Ann Handley.

***

A few weeks ago, a ladybug magically appeared in the upstairs bathroom. I noticed it (her?) on a cold January day, the kind of New England day when the outside air slaps you straight across the face.

A few days later, I saw the ladybug again—still in the bathroom, now loitering on the sunny windowsill. The ladybug is motionless—maybe dead—but then suddenly on the move, taking itself for a walk around the window screen.

I watched it (him?) for a few minutes. It’s an incongruous scene: a ladybug—classic symbol of summer—strolling in the sun while just beyond it’s deep winter: 16 degrees with two feet of snow on the ground.

This ladybug has decided my bathroom is Bug Boca Raton. And she (I’ve decided she’s a she) is wintering here.

Where did you come from? How are you going to survive the winter? I ask her, interrogating her like a homeowners association compliance officer who’s just noticed an unauthorized guest at the pool.

* * *

Things feel unsettled lately. In business, algorithms are shifting. AI is flooding the internet. The old playbooks don’t really work anymore, and it’s harder to break through with a clear signal—especially in a world wired to reward speed: fast responses, fast output, fast growth.

For many of us, personally: It’s hard to know what to trust. What is real? What is not? Signals are harder to hear. Focus feels fragile.

I read that 2026 is the Chinese Year of the Fire Horse, which I misread as “Year of the Fire Hose.” And I think… yeah, “fire hose” sounds about right.

It makes me a little jumpy and panicky. How do we weather this storm?

I don’t think the solution is about better hacks and crushing my To-Do List or the secrets of The Perfect AI Prompt™. I don’t think it’s about this efficiency with this tool or that framework you need to have to thrive in this new climate.

The pressure is to move faster or fall behind.

But that’s exactly backward:

When speed becomes cheap, judgment carries a premium.

* * *

I learn that ladybugs move indoors when the outside world becomes inhospitable. They’re not confused or lost, exactly, and they’re not really hunkering down, either. They’re adapting.

The ladybug doesn’t know there’s two feet of snow on the ground. The ladybug doesn’t know it’s just winter; she doesn’t know spring will eventually come. All she knows is that conditions have changed.

In that way, she’s not so different from us.

* * *

When speed is cheap and volume is easy, generative AI can burp out 100 versions of a Facebook post. It can optimize the email subject line within an inch of its life. Everyone can make more things, faster. Speed alone is no longer an advantage.

So what’s left? It’s judgment. Taste. Context. Connection. Care for the long term.

It’s remembering why we’re here at all.

* * *

Reddit tells me to leave out water on a soaked paper towel with a bit of dried fruit. I put them both inside a small plastic container and place it on the windowsill.

I’ve named her Dot. I hope you like raisins, I whisper to Dot.

* * *

Why are we here? Our work has never just been about “output.”

Instead, good writing—and good marketing—is how ideas travel, how trust is built, how people decide what to pay attention to and what to believe. It’s about connecting with one person at one time, even if you’re speaking to millions.

That work doesn’t disappear just because technology gets faster and signals get louder. It becomes more important.

And in this season, it’s strangely a little radical to pause the relentless push forward long enough to ask better questions. That pause is how judgment re-enters the room:

Is this worth doing?
Is this actually helping someone?
Would I approach this differently if the platform/algorithm changed tomorrow?

* * *

Dot has made the little container her home. When the sun disappears below the horizon, she wedges herself into the groove in the plastic cover—she almost gave me a heart attack when I once adjusted the cover and nearly squished her.

I tell the housekeeper about Dot so she doesn’t accidentally vacuum her up. I’m a little embarrassed to tell her—I see how crazy this probably looks. But whatever.

A few minutes later she comes downstairs. “So,” she says. “I notice you put out food? For a bug?”

* * *

So where does this leave us? How do we do work we’re proud of? How do we prioritize health and well-being in the Year of the Fire Hose?

Here are three places I’m choosing to pause on purpose:

What’s one thing worth protecting right now because it actually compounds over time?

One relationship. One audience. One practice. One project.

For me, that’s my daily analog-writing practice. It’s also a more-recent weightlifting practice. Both are on my calendar every morning—non-negotiable, like a court date.

Where can technology remove drag—but (important but!) without eroding taste and judgment?

I’m not anti-AI. Tools are fine. But they are tools—they aren’t YOU. Choose deliberately where to let them in. Saying no is a choice, too.

Where could a small pause deliver an outsized outcome?

Five minutes before hitting send. A breath before saying yes. A day before shipping the final. An analog rough draft instead of one typed on a laptop. I’ve realized how reactive I am. I’m trying to change that.

Anyway… those are mine.

I don’t know what your pause is. But I suspect you already do.

* * *

I watch Dot perch on a plump raisin that’s 3 times her size.

Is this insane? What am I doing? Why do I care as much as I do?

I don’t really know. 

But maybe it’s this: Caring about small things is how we care about bigger things.

Maybe this has occurred to you already… but suddenly I think… WAIT.

Is this a feature? Or is it… a bug?

* * *

This winter gives us a mental shift, a way of clarifying what matters.

Conditions always change. What doesn’t change is the choice we have of where we put our attention.

Maybe that’s a feature. Maybe it’s a bug. Maybe it’s both.

* * *

Every morning I do a wellness check on Dot. Every evening I notice how she’s climbed into a crevice. It’s silly. It’s routine now.

I make sure she’s hydrated. I make sure she doesn’t get vacuumed up. I’m getting her through the winter.

She has no idea how good what’s coming next will be.

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