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.

The post A Ladybug in Winter appeared first on Ann Handley.

Tell me you’re a writer without telling me you’re a writer. I’ll go first.

I’m standing in the thin light of the fridge this morning, reading the copy on the side of an Oatly milk container. I am interrogating the word order.

The copy reads:

“We only know oats.”

Oatly copy is wild and wildly entertaining; I’ve written about it before in Milking Brand Voice. I also really, really like Oatly’s oat milk. But that morning by the fridge light I look at the Oatly carton and I think: “This phrase feels off.”

Then I realize why:

Instead of: “We only know oats,”
It should read: “We know only oats.”

Why exactly though? And why does such a tiny thing as word order matter—especially now, in the age of AI? (We’ll get to that in a bit.)

The Nerdy Why

In English, the word only modifies whatever immediately follows it.

Move it, and you change the meaning of the sentence entirely:

• “I only called her” = I called; I didn’t email or text.
• “I called only her“ = She’s the only person I called.
• “Only I called her” = I was the only one who called.

Only is wandering around inside that sentence like the last person standing in musical chairs—desperately searching for meaning.

See? Same words. Completely different meanings.

Back to Oatly

Here’s what the phrase on the Oatly carton actually says:

• “We only know oats” = The only thing we do with oats is know them.
  
  We don’t grow them, process them, master them, or turn them into a delicious dairy alternative with a snarky tone of voice. We just… know about them.
  
  That suggests limitation—as if Oatly is apologizing for its lack of expertise.
  
  It has a sheepish, deficient quality when you think about it. (And, yes, we are thinking about it. Because honestly I’m in this deep so let’s keep going.)

Now swap the order:

• “We know only oats“ = Oats are the exclusive focus.
  
  Oatly knows oats inside and out. Oatly loves them. Celebrates them.
  Oatly knows diddly about wheat, quinoa, or flax.
  
  We know only oats is a declaration of specialization. It’s confident and intentional. It says: “We at Oatly have chosen to master oats exclusively! We are OAT PEOPLE.”

There’s brain science behind this, too. Our brains give extra weight to the end of a sentence—linguists call it, well, end-weight. The last words—”only oats”—stick with us and shape our overall impression.

It’s subtle. Most people would never consciously register it. (Fewer still would write a few hundred words about it lol.) 

But still their subconscious has already formed an opinion about Oatly’s expertise before they’ve even finished reading.

So What, Eh?

Why does this matter? Let’s experiment and apply this rule more broadly:

I only write with pencils = limitation; you don’t do anything else with pencils (like rewind cassette tapes 😉)
I write only with pencils = passionate devotion to the pencil cause!

We only buy from startups = we don’t sell to them, for example
We buy only from startups = you confidently state your preference

Word order isn’t just cosmetic. This isn’t just me being obsessive about tiny details on a sub-zero morning in Boston and having a little fun (although those things are true). The bigger truth that goes beyond milk cartons: 

Word order can fundamentally change meaning.

One word-order change transforms a sentence.

One word change declares identity.

If you’re trying to position your brand as expert specialists rather than accidental amateurs… well: maybe you know only oats.

Which Brings Us Back to AI

Generative AI is very good at generating language that sounds right and seems right. 

What it’s not great at is judgment: choosing one word order over another because of what you want to signal.

I have no idea who wrote Oatly’s carton copy. This isn’t about them. But it is about a tool that will confidently plop out onto its conveyor belt, “We only write with pencils.”

It won’t pause to consider whether you mean limitation… or devotion.

It won’t stand in front of your fridge in the weak light and feel a low-grade existential itch about word order.

That itch is judgment. It’s taste.

AI knows alllll the words.

Only you and I decide what they mean.

The post Tell Me You’re a Writer Without Telling Me You’re a Writer appeared first on Ann Handley.

***

The post 13 Analog Gifts for Marketers, Writers, Creatives, You appeared first on Ann Handley.

***

Two weeks ago, I ranted about Justice for Em Dashes.

You know how you put something out in the world and your brain bullies you? “Weirdo. That’s a little too specific to your nerdy little heart,” your brain says.

Your gut piles on: “No one is going to care about Em Dashes.”

You send anyway. Then:

Your inbox blows up. On LinkedIn, it goes bananas—4,200 reactions and counting.

Two weeks ago, both my brain and my gut were totally wrong. Get in, losers! We’re building a store!

I call my co-conspirator, web designer Michelle Martello.

“What do you know about merch?” I ask her.

Michelle: “Enough to be dangerous.”

* * *

When something goes unexpectedly bananas, you have two choices: You can ignore it and move on. Or you can decide to make it your whole personality.

I chose the latter.

The store that Em Dash Revolutionaries like you and me have been WAITING FOR is now live!

The store is a seasonal pop-up: open only through the end of the year. Just in time for holiday giving.

 The Justice for Em Dashes merch is here. 

All proceeds from this store will benefit charity, split between two animal-rescue groups: the Humane World for Animals (formerly known as the Humane Society); and True & Faithful Rescue, which rescues and rehomes senior dogs.

The latter is an issue near and dear to my heart—senior pets are too often overlooked, especially those with medical needs. My sweet girl Abby lived to be 16, and she spent her final years as a small, opinionated senior citizen who believed organic chicken was a constitutional right. I miss her.

If you care about em dashes—and clearly we’re those people—thank you for supporting this pop-up and the mission behind it.

The post Em Dash Merch – Limited-Time Fundraiser! appeared first on Ann Handley.