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Welcome to the 131st edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: The 3 C’s of Story

• AI Tip: Save the horsepower for where it actually moves the needle.

• The Revision Where Good Work Goes to Die (via Copywriter Collective)

• Why the Rule of 3 Makes You a Better Communicator (via INC)

• Marketing needs AI outcomes, not more AI pilots (via MarTech)

• Principles Over Pressure: Sticking To Your Values During Mid-Year Sales Pushes (via The Copy Minimalist)

• Podcast Pick: Choose the Right Channel: How Stanford Finds Its Voice

• Swipe File Additions

• Job Opportunities

This issue of the Weekly Round Up is brought to you by Shlomo Genchin:
CopyTemplate

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My friend Shlomo just launched CopyTemplates ($97) – a library of 63 proven copywriting techniques, each comes with handpicked examples (500+ in total), plus 70+ copy-paste AI prompts and Claude skills.

It’s the best resource I’ve seen for writing headlines, with or without AI.

Get it for $97 for a limited time

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Every story that sells has the same skeleton:

1. Character

2. Conflict

3. Change

Strip away the branding, the product, the channel — every story that actually moves someone has all three. Remove any one, and the whole thing collapses.

Character: someone the reader recognizes. Could be a customer, a founder, a version of themselves.

Conflict: the thing standing in their way. Without tension, there’s no reason to keep reading.

Change: what’s different now. No change, no point.

Most “brand stories” only have one or two of these. They introduce a character, skip the real conflict, and jump straight to “and now we’re great.”

But that’s not a story. There’s no depth.

If you want your story to actually sell, give the reader all three – especially the conflict! It’s the part everyone’s most tempted to cut, but it’s almost always the part doing the most work.

AI Insight of the Week

Use your most powerful model for the first draft. Switch to a simpler one for iteration.

Most people pick a model and stay on it for the whole task, but that’s backwards.

The first draft is where the real thinking happens — structure, angle, the core argument. That’s the part you want your strongest model on. Get the hardest cognitive work done up front, when the stakes for quality are highest.

But once the draft exists, the work changes. You’re tightening lines, adjusting tone, trying variations. That’s lighter lifting, and a faster, cheaper model handles it just as well (and often faster, which matters when you’re iterating quickly).

So my advice? Front-load the intelligence. Save the horsepower for where it actually moves the needle.

Must-Read Articles

You Should Read This Too:

THINK FAST TALK SMART
Ep. 299: Choose the Right Channel: How Stanford Finds Its Voice

🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Stanford’s VP of communications runs every story through one question before a single word gets written: short video, longform, or media pitch — and sometimes the answer is “let a journalist tell it, not us.” Farnaz Khadem breaks communication down to three things: know your goal, know your audience, know your data, plus a crisis-comms rule worth stealing. Anybody who communicates should listen to this!

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

HOWLER BROTHERS

Format: Email
Why I like it: If there’s a killer/fun story behind your product – share it! I actually own this shirt and I didn’t know the legend behind it. Honestly, pretty damned cool.

SEED

Format: Email
Why I like it: The subject line leaves me wanting, but the guts of the email (pun intended?) are fantastic for someone who’s product aware and looking for a reason to switch. It pulls all the social proof levers.

BITE

Format: Email
Why I like it: A great example of the PAS copy framework at play. And honestly, more CPG/wellness/supplement brands should do this.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Creative Director, Copy and Content (Agency)
  Remote

• Creative Lead, Marketing (Agency)
  Remote

• Senior Copywriter (Agency)
  Remote

• Marketing Content Writer (B2C)
  Remote

• Senior Copywriter (Tilt)
  Remote

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

Subscribe now

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Welcome to the 130th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: An email is not a landing page. ****

• AI Tip: Revisit your Project system prompt quarterly.

• The human-centered approach to AI adoption (via ActionRocket)

• Marketing measurement is breaking under its own complexity (via MarTech)

• The Psychology Behind Headlines That Make Customers Click: Understanding the Science of Attention (via The Copy Minimalist)

• Podcast Pick: The Anatomy of a High-Converting Listicle

• Swipe File Additions

• Job Opportunities

This issue of the Weekly Round Up is once again brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That's not an accident — it's what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that. Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

An email is not a landing page.

They’re not the same job, they don’t follow the same rules, and when you write them like they are, both suffer.

A landing page has one job: close. It gets a focused, distraction-free environment and has room to handle objections, build proof, and walk someone all the way to a decision.

An email has a different job: earn the click.

That’s it.

Get them curious enough, interested enough, or compelled enough to want more — then get out of the way.

When you try to do the landing page’s job inside the email, you end up with something too long to read and not focused enough to convert. You’ve explained everything, so now there’s no reason to click. And you’ve buried the CTA somewhere after three scrolls.

Write the email to earn the click. Let the landing page do the closing.

Two jobs. Two pieces of copy.

Don’t make one do both.

AI Insight of the Week

Revisit your Project system prompt quarterly. Your standards evolve, so your Project should too.

Most people set up a Project system prompt once and never touch it again.

But your taste has sharpened, your audience understanding has deepened, and you’ve learned what Claude does well in this context and where it keeps missing.

None of that is reflected in a system prompt you wrote on day one.

A quarterly revisit doesn’t have to be a rebuild. Usually it’s smaller than that — tightening a constraint that’s been producing mediocre outputs, adding an example of a recent piece you’re proud of, or removing a rule that made sense then but doesn’t now.

Think of it like a performance review. Not for Claude, but for the brief you gave it.

Must-Read Articles

The human-centred approach to AI adoption (via Action Rocket)

Why I recommend it: ActionRocket didn’t start their AI rollout by asking “where can we use AI?” — they started by asking “what slows people down?” The result: automations nobody misses, copywriters who own more of the work that matters, and the irony that adding technology made the agency more human, not less.

Marketing measurement is breaking under its own complexity (via MarTech)

Why I recommend it: The average marketing team uses six different tools to measure performance — and only 18% say they can clearly see what’s working. More data didn’t solve the problem, it deepened it: every channel tells a different story, and the tools built to connect them are the least commonly used ones in the stack.

The Psychology Behind Headlines That Make Customers Click: Understanding the Science of Attention (via The Copy Minimalist)

Why I recommend it: Your brain makes engagement decisions in 50 milliseconds — long before rational thought kicks in. This deep dive covers the five psychological triggers behind every headline worth clicking: novelty, loss aversion, curiosity gaps, pattern disruption, and emotional priming. Plus a practical framework for knowing which trigger to pull based on where your customer is in their journey.

You Should Read This Too:

LIMITED SUPPLY
The Anatomy of a High-Converting Listicle
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: A “10 reasons why” listicle converts at 6-7% versus 1-1.5% on a standard product page, because it qualifies traffic without directly selling. Nick Sharma walks through real listicle teardowns — the two-layer-deep angle trick (”for people who drink regularly,” not just “for everyone”), why mobile-first wireframing beats designing for desktop, and where AI actually helps versus where it just produces slop.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

MATT FROEHLICH

Format: LinkedIn
Why I like it: My former coworker is a BIG sports guy (and a wildly talented growth strategist for DTC brands). Thought this was a creative way to announce his impending availability in the job market. (And if you’re hiring, he’s a catch).

HUCKBERRY

Format: Email
Why I like it: If you’re looking for a way to increase AOV (average order volume), featuring products that go well together in an email are a great way to do that. Huckberry’s also done “capsule” emails in the past, which is fantastic for apparel brands.

PAYA

Format: Email
Why I like it: Great example of a problem/agitation/solution at play for a skincare brand.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Creative Content Lead (Bobbie)
  Remote

• Creative Content Lead (CPG Brand)
  Remote

• Email Copywriter (Agency)
  Remote

• Copywriter (Astrally)
  Remote

• Senior Content Writer (Compound Content Studio)
  Remote

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

Subscribe now

There’s a particular kind of pressure that shows up around the middle of June, and if you’ve worked in this field long enough, you can feel it coming before anyone puts it into words.

The first half of the year is closing out. Someone has done the math on where the numbers actually landed versus where they were supposed to, and the gap is bigger than anyone wants it to be.

So the meetings get rescheduled a little earlier, the messages get a little shorter, and eventually it arrives in one form or another: we need to push harder this month.

If you work in-house, it usually sounds reasonable. Leadership wants the messaging punched up, the calls-to-action sharpened, the offers pushed a bit more aggressively.

If you freelance, it tends to come from a client who’s suddenly asking for the countdown timer, or the “only a few spots left” line, or the urgency you both know isn’t quite real.

And here’s what makes this moment genuinely hard to navigate, rather than just unpleasant. Nobody’s asking you to lie. That would be easy. A clear request to deceive someone is something most of us would recognize and refuse. What you actually get is something much softer and much harder to push back on.

You get asked to be more aggressive, more urgent, more compelling. And every individual request, looked at on its own, sounds completely fair.

You’re never handed one big decision you can plant your feet against. You’re handed a dozen small ones, each of them reasonable, and somewhere in the middle of saying yes to all of them you’ve ended up somewhere you wouldn’t have chosen on purpose.

Let me give you a version of this I’ve seen play out more than once, because it makes the whole thing concrete.

Picture a brand with a single evergreen offer, the same deal running quietly in the background all year long. Mid-June rolls around, the numbers are soft, and someone has what feels like a perfectly good idea: take that evergreen offer and dress it up as a Father’s Day sale.

So the emails go out. Final hours. Last chance to get twenty percent off for Dad. The countdown timer ticks down toward zero, and everyone watches the orders come in.

Then the next morning arrives, the “sale” ends, and the evergreen offer simply resets. Same price. Same terms. There was never anything to miss in the first place.

I want to be fair about this, because nobody in that room thought of themselves as dishonest. They had a real offer and a real date on the calendar, and stitching the two together felt less like deception and more like resourcefulness.

But that’s exactly why this is worth talking about. The problem here isn’t villains. There usually aren’t any. The problem is what happens to good people and good brands when the pressure shows up and starts quietly bending things, one reasonable inch at a time.

Pressure doesn’t test your marketing. It tests whether your principles were ever real.

My hot take: values are free in January.

Every brand has them. They’re in a deck somewhere, a Notion doc, a tidy little list on the About page. “We believe in honesty.” “We’re a premium brand.” “We serve this customer better than anyone.” Easy to write. Costs nothing to say.

But June is when those values get a price tag.

There’s a difference between a value you state and a value you hold, and the only way to ever know which one you’ve got is to wait until it costs you something.

Revenue.
A client.
An easy win you have to walk away from.

Until the bill comes, you genuinely don’t know. You’re just guessing about your own character. And most people guess generously.

Now, when we talk about “principles” in marketing, everybody jumps straight to honesty. Don’t deceive people. Fair enough. The fake Father’s Day sale is the obvious version.

But honesty isn’t the only thing pressure comes for. There are two others that get abandoned just as often, and a lot more quietly.

The first is positioning.

Say you’ve decided to be the premium option in your market. Good. That’s a real decision with real teeth. Then Q1 comes in soft, and there’s a discount sitting right there on the table, the easiest yes you’ll find all month.

But a discount doesn’t just move units. It tells your market something. It says you were never really the premium thing. You were the regular thing, waiting for a reason to go on sale. And once you’ve taught people to wait for that reason, they will. Forever. You don’t get to charge a premium and run a sale rack at the same time. One of them wins, and if you won’t choose, the pressure chooses for you.

The second is conviction.

Maybe back in January you decided to go hard on one kind of customer. One segment, one category, one group you were going to serve better than anyone else in the space. Smart. Focused. The kind of bet that pays off over years.

Then June hits and it’s harder than you thought. You’re hitting walls. The numbers are slower than the easy stuff would’ve been. And the tempting move is to quietly widen the net. Stop being the brand for them and start being the brand for whoever’s buying that week.

The principled move is to assume the hard part is the work. Not a sign you bet wrong.

So here’s the thread tying all three together.

A principle isn’t just “don’t lie.”
A principle is any decision you made in a calm moment that the market will later pay you to unmake.

Pressure is the invoice.

Which means the pressure isn’t the enemy here. It’s the test. It’s the only honest test you get all year of whether those January values were ever load-bearing or just decoration.

This is the whole premise of principle-based marketing: the values only matter at the moment they cost you something.

How the drift actually happens

But here’s the thing: nobody decides to become a manipulative brand. What they decide is much smaller.

They decide one deadline can be “basically real.” They round one number up because it’s close enough. They let one testimonial stand because it’s “essentially what the customer meant.” Each move is defensible if you hold it up by itself. Anyone would sign off on it.

But it’s the sum that’s the problem! And unfortunately, nobody ever looks at the sum.

Go back to that Father’s Day sale for a second.

No one in that room set out to trick anybody. They had a genuine offer. They had a real holiday on the calendar. Wrapping one in the other felt like resourcefulness, not deception. Yet that’s exactly how the line gets crossed! Not by somebody deciding to cross it. By nobody noticing it was there.

Pay attention to the language, too, because the compromises always show up wearing respectable clothes.

You don’t tell yourself you’re faking urgency. You’re “creating urgency.” You’re not caving on price. You’re “testing a stronger offer.” You’re not abandoning your customer. You’re “expanding the audience.” The words are doing a job, and the job is to let you feel fine about it.

Here’s the part I really want you to pay attention to…

Your customers notice.

Maybe not consciously. If you stopped one and asked, they probably couldn’t point to the exact email that did it.

But the sale that wasn’t really a sale registers somewhere. It gets quietly debited from an account you can’t see on any dashboard, the one labeled do I actually believe these people.

And you never get an alert when that balance drops. You just find that your next campaign works a little less well than it should, and your one after that, and you sit there blaming the subject line. You tune the copy. You swap the image. You never once suspect the real problem, which is that you spent down your credibility for a 20% bump in June and the interest is coming due all year.

People aren’t dumb.
They clock the move.

The only question is whether you’ve decided to make them pay for noticing. (This is the same buyer instinct I wrote about in “the one thing AI can’t learn”: conversion runs on a felt sense of trust, and customers register when it’s missing long before they could explain why.)

Decide before the pressure does

So what do you actually do about it?

Not a framework. I’m not going to hand you a five-step system, because a system is just one more thing to abandon when things get hot.

Here’s the real move, and it’s almost annoyingly simple.

You decide before the pressure arrives.

Principles only survive a crunch when you’ve already turned them into decisions. Calls you made when you were calm, that you then flat-out refuse to reopen when you’re not. The whole trick is taking the decision out of the hot moment, because the hot moment is exactly when you make your worst calls.

A few of mine look like this:

• Deadlines are real or they don’t exist. No resetting timers.

• We only claim what we can actually show.

• We don’t discount our way out of a slow quarter.

• The customer we committed to in January is still the customer in June. Especially when it’s hard.

Notice those aren’t clever. They’re not supposed to be. They’re supposed to be boring and settled, so that when somebody floats the fake countdown idea at 4pm on a Friday, the answer’s already sitting there.

You don’t have to relitigate your ethics on the spot. You just point at the thing you decided months ago, back when you could think straight.

If you lead a team, this matters even more, and it’s mostly on you. These decisions have to be said out loud, to your people, before the push. Because if you haven’t, you’ve left some junior writer alone in a doc at the end of a long week trying to figure out whether “hit the number” quietly cancels out “hold the line.”

That’s not a fair thing to make them guess. Decide it for them, ahead of time, so they never have to negotiate it solo.

And if you’re a team of one, write them down anyway and stick them somewhere you’ll see them. Because the conversation with a pushy client goes completely different when you walk in having already decided where you stand. You’re not deciding under fire. You’re just reporting a decision you already made.

Under pressure, you don’t rise to your values. You fall to your defaults.

So the only thing that actually matters is what you built your defaults to be, and you build those on a quiet Tuesday in March, not in the middle of a June scramble.

Holding the line isn’t refusing to sell

Now, I know how some of this can read. Like I’m telling you to go soft, and sit on your hands and run gentle little campaigns and leave money on the table to keep your conscience clean.

No, I’m not. That’s not it at all.

Urgency is great when the deadline is real.
Scarcity works when the stock is actually low.

Strong offers, direct asks, hard closes, the occasional genuinely-ends-Friday sale, all of it is fair game when it’s true. A premium brand can have an absolute monster of a quarter. It just does it by selling the premium harder, not by becoming the clearance brand for 30 days and hoping nobody remembers in July.

The pressure to sell was never the problem. The shortcut is.

And here’s the thing about the shortcuts – they feel like effort, but they’re the opposite. The fake deadline, the panic discount, the suddenly-much-bigger audience, those are all things you reach for instead of solving the actual problem. They’re the easy door.

The principled move and the genuinely creative move turn out to be the same move almost every time, which is to push through the hard thing rather than sneak around it.

The bonus, and it’s a real one, is that the honest version usually just works better.

True urgency beats fake urgency, because when you say “Friday” and mean it, people learn that your next “Friday” is worth acting on.

Held positioning beats a discount habit, because you keep both your margin and your meaning. And conviction beats chasing, because you end up genuinely great at one thing instead of forgettable at five.

Doing it right isn’t the noble, costly option. Most of the time it’s just the option that’s still working a year from now.

What mid-year pressure actually reveals

The push isn’t going anywhere. It shouldn’t. Mid-year pressure is a normal part of doing this work, and honestly, some of it is good for you. It sharpens things.

It’s just that it also tells you the truth.

Every June, the pressure walks in and quietly itemizes everything you said you believed back in January, and puts a price next to each one.

The fake sale you didn’t run.
The discount you didn’t reach for.
The customer you didn’t abandon when it got hard.

That bill is the most honest feedback you’ll get all year.

So I’ll leave you with the question I keep coming back to.

Which of your principles has actually cost you something this year?

Because if the answer is none of them, that’s worth sitting with. It doesn’t mean you’re disciplined. It might just mean nobody’s pushed you yet.

Subscribe now

Welcome to the 129th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Your word choices don’t just say things. They reveal things.

• AI Tip: Projects vs. Skills (when to use both)

• Disagreeing with Rick Rubin (via Around the Bonfire)

• Why Great Creatives Keep Delivering Average Work (via Copywriter Collective)

• Employee Ownership is Not a Culture Strategy (via Branding Strategy Insider)

• Podcast Pick: 17 Things Brands Get Dead Wrong About Millennials

• Swipe File Additions

• Job Opportunities

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That's not an accident — it's what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that. Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Your word choices don’t just say things. They reveal things.

Every word you pick signals how you see the person reading it.

Write “simple” instead of “easy” and you’re implying they need things dumbed down. Write “just click here” and you’re signaling that their hesitation is an inconvenience. Write “as you probably already know” and you’re either being condescending or covering your own bases.

Readers feel this. They may not be able to name it — but they respond to it.

The best copy treats the reader like a smart person who has a real problem and deserves a straight answer. Every word either reinforces that or undermines it.

So next time you’re editing, don’t just ask is this clear?

Ask: what does this word say about how I see the person reading it?

AI Insight of the Week

A Project sets the world. A skill teaches the job. You need both.

Most people build one or the other and wonder why their outputs are inconsistent.

A Project system prompt answers the contextual questions (e.g., who Claude is, who the audience is, what good output looks like, etc.). It’s the operating environment.

A skill file answers the procedural questions (e.g., the framework, the process, the steps for executing a specific task well, etc.). It’s the methodology.

They’re not redundant.
They’re layered.

The Project without the skill gives you the right voice but no repeatable process. The skill without the Project gives you a solid process but no context.

Build both.

That’s when Claude stops feeling like a tool and starts feeling like a specialist.

Must-Read Articles

Disagreeing with Rick Rubin (via Around the Bonfire)

Why I recommend it: Rick Rubin says the audience comes last. Marketers say the audience comes first. Kevan Lee and Shannon Deep say both are right — because “audience” isn’t one thing. There’s the imagined audience (the committee in your head), the real audience (people with actual problems), and the future audience (the people who’ll recognize the work once it exists). Most watered-down creative work comes from obeying the first one.

Why Great Creatives Keep Delivering Average Work (via Jake Stafford, Copywriter Collective)

Why I recommend it: After decades placing creative talent, the pattern is clear: when brilliant writers deliver average work, the brief is almost always the culprit. A vague brief, a review-by-committee, and a culture of playing it safe will produce exactly what you’d expect — because great creatives don’t bring their best to rooms where bold ideas keep getting sanded down in approval.

Employee Ownership is Not a Culture Strategy (via Branding Strategy Insider)

Why I recommend it: “We are employee-owned” is a structure, not a culture strategy — giving everyone a key to the building doesn’t tell them what kind of business to build inside it. A useful reframe for anyone leading a team: ownership creates pride, but pride without direction doesn’t create customer trust. Culture does.

You Should Read This Too:

BRAIN DRIVEN BRANDS
17 Things Brands Get Dead Wrong About Millennials
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Millennials aren’t 25, aren’t in their prime spending years, and own 3% of the wealth boomers had at the same age — so stop marketing to them like they are. Sarah and Nate break down 17 things marketers get wrong, from the BS detector built by a lifetime of ads to why “this salad is the sigh of relief you needed today” is the fastest way to lose us forever.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

PADDY POWER

Format: Billboard
Spotted By: Paul Smith
Why I like it: A marketing “gamble” for a gambling platform. Nice.

HOLLOW

Format: Email
Why I like it: Great Fathers Day themed email (and I love a good theme). I am a grill master. Definitely need to get myself a pair.

PATH PROJECTS

Format: Email
Why I like it: These guys don’t just make running shorts, they’e essentially solved a problem for the most serious distance runners – a solve that sets them apart. And the headline sums it up perfectly.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Associate Creative Director, Copy (YouTube/Social)
  Remote

• Marketing Data Analyst
  Remote

• Email Copywriter (Agency)
  Remote

• Content Lead
  Remote

• Senior Copywriter
  Remote

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

Subscribe now

Subscribe now

Welcome to the 128th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: When editing REALLY starts.

• AI Tip: End every strategic session by asking Claude to summarize the decisions made.

• The Psychology Behind Inbox Placement (via InboxAlly)

• I’ve Written 47 CTAs. Only One Worked (via Copywriter Collective)

• “Better Copy” Kills Positioning (via Kate Guerrero)

• What the Best Copywriters Will Have in Common 10 Years From Now (via The Copy Minimalist)

• Podcast Pick: The Hook Secrets That Make You Keep Watching

• Swipe File Additions

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That's not an accident — it's what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that. Get early access here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Most copywriters edit the same way they were taught to write.

Start at the top.
Work down.
Clean up what you find.

But that’s not editing, that’s proofreading.

Real editing starts BEFORE you touch a single word.

Before I read a draft, I orient myself.

I know the audience.
I know where they are in terms of awareness.
I know how sophisticated this market is.

I go in with a frame, like Schwartz said, and I have an idea of what I’m about to read. It’s that frame that allows me to see structural problems that have nothing to do with word choice.

A line can be grammatically clean and still be wrong.

Wrong for where this reader is.
Wrong for what they believe right now.
Wrong for the sequence of the argument.

That’s what I’m looking for on pass one: whether the argument is landing in the right order for the right person.

If it isn’t, nothing else really matters.

You can’t edit your way out of a broken structure. You can tighten every sentence and still end up with copy that doesn’t convert, because the problem was never the words in the first place. It was the sequence.

Remember this: structure first.
Always.

If you’re spending your first pass fixing commas, you’re editing the wrong thing.

AI Insight of the Week

End every strategic session by asking Claude to summarize the decisions made.

Not a recap of the conversation – the decisions.

There’s a difference. A conversation summary tells you what was discussed. A decisions summary tells you what you actually committed to, and that’s where the surprises live.

Most strategic sessions with Claude produce more conclusions than you realize. You agreed on an angle. You ruled out an approach. You made an assumption about the audience and kept moving. None of it felt like a decision in the moment, but it was.

Ask Claude: “What decisions did we make in this conversation?” and read it carefully. You’ll almost always find at least one assumption you didn’t know you’d made.

Must-Read Articles

The Psychology Behind Inbox Placement (via InboxAlly)

Why I recommend it: Inbox placement isn’t just a technical outcome, it’s a behavioral one. Mailbox providers aren’t checking your DNS records, they’re watching what your subscribers do in the first fraction of a second. Kath Pay applies Kahneman’s System 1/System 2 framework to deliverability and makes the case that you’re not just optimizing emails, you’re conditioning expectations.

I’ve Written 47 CTAs. Only One Worked (via Copywriter Collective)

Why I recommend it: After 47 versions of a two-word button, the winner was “See the prices.” Not punchy. Not branded. Not elevated. Just a doorway that told the reader exactly what was on the other side, and doubled the click-through rate against “Discover the Collection.” The whole piece is a reminder that a CTA isn’t a headline. It’s a promise.

“Better Copy” Kills Positioning (via Kate Guerrero)

Why I recommend it: Positioning sessions feel great until the copy ships — and suddenly the founder wants to say something completely different. Kate Guerrero nails why: strategy is theoretical, copy is public. A great copywriter’s job isn’t just to write well. It’s to hold the line when fear shows up dressed as a feedback note.

You Should Read This Too:

JOANNA WIEBE
The Hook Secrets that Make You Keep Watching

🎧 Watch on YouTube

Why I recommend it: Eight strategies for hooks built on a century of direct response thinking and updated for the 30-second scroll. The most useful framework: every piece of content needs a super hook (the big open question held until the end), nested hooks underneath it, and mini hooks every 12–15 seconds. If the tension closes too early, the brain moves on…

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Pretty Fly Copy

PITVIPER

Format: Email
Spotted By: Jessica L.
Why I like it: 100% the last thing I’d expect to see from a brand in my inbox. Absolutely love the quirkiness and personality this type of campaign demonstrates.

CHEWY

Format: Email
Why I like it: I thought this was great for a solution aware/most aware audience (me!). It includes all the right persuasion levers for me (outside of a discount), and a hilarious product pic to boot.

PAKT

Format: Email
Why I like it: There’s a trend I’ve been noticing lately with a lot of DTC brands: intentional storytelling via email. It’s a welcomed shift, imo. But I like how this begins by placing a demand on your imagination as a way to prime you for positioning their product as a value-add to said imagined situation. So good!

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Creative Lead, Performance Copy
  Kin Insurance | Remote

• Sr. Lead Product Copywriter
  Hims | Remote

• Copywriter and Creative Strategist
  Super Speciosa | Remote

• Snr. Content Copywriter
  myTomorrows | Remote

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Everyone has an opinion on what copywriters need to learn right now (heck, even I do).

More hooks. Better prompts. Shorter sentences. Longer emails. Be on LinkedIn. Don’t be on LinkedIn. Be on Substack. Don’t be on Substack.

The advice isn’t exactly wrong, but it’s mostly aimed at the surface, and the gap opening up in this field isn’t a surface problem.

The writers pulling ahead aren’t the ones who found a better hook formula. They’re the ones who got sharper about how they think about the work before they write a single word.

And most conversations about “leveling up” are completely missing it.

Why Craft Alone No Longer Separates Strong Copywriters From Average Ones

For a long time, the path forward was clear.

Study the greats.
Learn the fundamentals.
Write more.
Get better feedback.
Repeat.

That path still works. Craft is not dead. Writers who can’t construct a sentence that moves someone aren’t going to be saved by strategic thinking alone.

But here’s what I’ve noticed after so many years in this field: craft rarely explains the gap between writers who consistently produce work that performs and writers who don’t.

The difference almost always lives upstream of the draft. It’s how they approach the problem before they even open a blank document.

The writers who plateau are usually technically capable. They can write a clean sentence, follow a brief, and hit deadlines. But ask them why a piece isn’t working, and they’ll look at the words. Rarely the thinking behind the words.

That’s the ceiling most writers bump into.
And more writing reps won’t raise it.

What Strategic Thinking in Copywriting Actually Means

Strategic thinking about copy means being able to answer four questions before you write anything.

What is this supposed to do?
For whom?
At what point in their decision-making?
What does this person already believe, and what do you need them to believe differently by the end?

Most writers can execute a brief, but fewer can interrogate one.

There’s a real difference between a writer who gets an assignment and starts writing, and a writer who gets an assignment and starts asking questions. Not to be difficult, but to be useful. Because a brief that doesn’t answer those questions is a brief that will produce mediocre work no matter how good the execution is.

This isn’t a complicated idea, but it does require a shift in how you see your job.

Your job isn’t to fill space with words that sound like marketing. Your job is to move a specific person from one mental state to another. The writing is how you do it. The thinking is why it works.

And when you begin to internalize that, everything changes. You stop asking “how should I write this?” and you start asking “what does this person need to feel, see, or believe for this to work?”

Interested in sponsoring an issue of The Edit? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

How to Develop an Editorial Eye: Diagnosing Copy Problems Clearly

The second skill most writers have never been taught: how to critique copy clearly.

Editorial skill in copywriting is the ability to name why a piece isn’t working, not just sense that it isn’t. A lot of it’s because they’ve been taught to write, not to evaluate.

There’s a difference between sensing that something doesn’t work and being able to name why. “This feels off” is not a usable note. “The reader doesn’t feel recognized in the first two paragraphs, so they have no reason to keep going” is.

This matters for your own work. Writers who can diagnose their drafts clearly edit faster and better. Those writers stop putting band-aids over symptoms and start fixing causes.

It matters even more when you’re reviewing someone else’s work, or when you’re working alongside AI-generated drafts (because that’s increasingly part of the job).

As teams generate more first drafts by more means, the human contribution shifts toward judgment – toward knowing what’s missing, what’s off, what needs to be rethought. If you can’t articulate what’s wrong and why, that judgment call isn’t available to you.

Editorial skill is learnable. It starts with reading copy the way a diagnostician reads a patient chart, not looking for what’s there, but looking for what the work is trying to do and whether it’s doing it.

Three questions to ask when diagnosing any piece of copy:

1. Does the reader feel recognized within the first two paragraphs?

2. Is there a clear belief the copy is trying to shift, and does it actually shift it?

3. Does the call to action follow logically from the argument built above it?

What Performance Literacy Means for Copywriters (And What It Doesn’t)

Writers don’t need to become analysts, but they do need to care about whether their work is doing its job.

Performance literacy for copywriters means maintaining a working relationship with data (e.g., open rates, click behavior, conversion trends, etc.). Not to become a numbers person, but to close the feedback loop between what you write and what happens when a real person reads it.

The writer who never looks at results is guessing every single time. Their intuitions might be good, but they’re not getting sharper because they’re not being tested against anything real.

The writer who only looks at results loses something else: their instincts, their voice, their willingness to try something that doesn’t have a precedent in the data.

What you’re after is informed judgment. You read the signals. You develop a point of view about what they mean. Then you make a call. That’s different from chasing whatever the numbers say, and it’s different from ignoring them entirely.

Closing the feedback loop doesn’t require a data background. It requires curiosity and a habit of asking: did that work? Why or why not?

How AI Tools Fit Into a Copywriter’s Workflow (And Where They Don’t)

Here’s where most conversations about the future of copywriting spend most of their time.

(Honestly, I’d rather spend less.)

Not because AI isn’t relevant. It is! And writers who are pretending otherwise are making a choice with real costs.

But the thing worth understanding isn’t how to use AI. It’s why some writers get so much more out of it than others.

The writers getting the most from AI tools aren’t the ones using them the most. They’re the ones using them most deliberately. They bring a clear question. They evaluate the output against their own judgment. They know what they’re looking for and they know when they haven’t found it yet.

The risk on the other side is real and worth naming: if you outsource your thinking to an AI tool, you don’t develop the judgment that makes you irreplaceable. You get faster at producing something. That’s not the same thing.

Where AI tools genuinely help copywriters:

• Pressure-testing a direction before committing to it

• Generating alternatives when stuck on an angle

• Surfacing patterns in performance data faster than manual review

• Drafting structural scaffolding to react to and edit

Where AI tools fall short:

• Determining what the work should accomplish

• Judging whether it’s accomplishing it

• Supplying the emotional authenticity that comes from lived experience, which, at the conversion layer, is what closes the gap between copy that reads fine and copy that actually works

I wrote about this in more depth earlier this year — specifically about the one thing AI can’t learn no matter how good your prompts get. The TL;DR version: at the conversion layer, emotional authenticity comes from lived experience. No input closes that gap.

The writers who will matter in the next ten years aren’t the ones who learned to prompt well. They’re the ones who kept sharpening the judgment that prompting is supposed to support.

The 4 Traits the Best Copywriters Will Share in 2035

The next generation of strong copywriters won’t be defined by how much they can produce, and they’ll likely share these four traits:

1. They think before they write. Strategic clarity about audience, moment, and belief-shift happens upstream of the draft.

2. They diagnose, not just produce. They can name why a piece isn’t working and fix the cause, not the symptom.

3. They close the feedback loop. They treat performance data as a sharpening tool, not a report card to ignore or a script to follow.

4. They use AI deliberately. They bring judgment to AI outputs rather than delegating judgment to them.

None of these are new skills. But in a landscape where production volume is increasingly cheap, they are the skills that compound fastest, carry the furthest, and matter most when the tools change again.

And they will change again.

So the real question worth sitting with: how much time do you spend thinking about the problem before you start solving it?

Your answer could very well separate you from the pack.

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Welcome to the 127th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Clarity = respect

• AI Tip: Opus is your strategist. Sonnet is your workhorse.

• Writing for Email: A Copywriter’s Accessibility Guide (via Action Rocket)

• Paid Isn’t Dead. But Your Playbooks Need an Upgrade (via MKT1)

• AI Adoption Fails at the Human Level (via MarTech)

• Podcast Pick: How to Enter “Flow State” on Command w/ Steven Kotler

• Swipe File Additions

• Job Opportunities

Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Unclear copy isn’t just a writing problem. It’s a respect problem.

When your brief is vague, your writer has to guess what you meant.
When your feedback is ambiguous, your editor has to guess what you want.
When your messaging is muddled, your customer has to guess what you’re selling.

And guessing is expensive! It costs time, creative energy, and trust.

Clarity removes decisions people shouldn’t have to make, and that’s true whether you’re writing for a customer or writing a brief for your team.

The principle: clarity is a form of kindness.

Write clearly, and you respect everyone downstream.

AI Insight of the Week

Opus is your strategist. Sonnet is your workhorse. Know which one the task actually requires.

Most people pick a model once and stick with it, but that’s leaving performance on the table.

Opus thinks harder. It’s better at nuanced reasoning, complex strategy, and tasks where the quality of the thinking is the output. If you’re stress-testing a positioning angle, mapping a content strategy, or working through a genuinely difficult brief — that’s something to use Opus for.

Sonnet, however, executes faster. It’s better at high-volume drafting, iteration, formatting, and tasks where speed and consistency matter more than depth. So if you’re generating subject line variants or reformatting a document, Sonnet gets you there quicker (and cheaper).

Match the model to what the task actually demands. Thinking or doing. That’s the whole framework.

Must-Read Articles

Writing for Email: A Copywriter’s Accessibility Guide (via Action Rocket)

Why I recommend it: A quick accessibility checklist for email copywriters. From writing CTAs that say what they actually do (not “click here”) to why caps and italics reduce readability for the people who need clarity most, these simple shifts make your emails work for everyone, not just the easiest audience to write for.

Paid Isn’t Dead. But Your Playbooks Need an Upgrade (via MKT1)

Why I recommend it: Paid isn’t dead, but the playbook of picking a channel and hoping for the best is. Emily Kramer makes the case for audience-first paid: enrich your accounts, load them into every platform, build suppression lists, and let paid learnings feed organic (and vice versa) instead of running them in silos.

AI Adoption Fails at the Human Level (via MarTech)

Why I recommend it: The biggest blocker to AI adoption isn’t the technology, it’s the scar tissue from every failed software rollout that came before it. This breaks down 5 psychological fears that keep leaders from saying yes (loss of control, identity threat, transition cost, shame, and past failure) and a practical framework for earning trust before you pitch the tool.

You Should Read This Too:

BIG THINK
How to Enter “Flow State” on Command w/ Steven Kotler

👉 Watch on YouTube

Why I recommend it: Flow isn’t a personality trait – it’s a neurological state you can engineer. Steven Kotler breaks down the triggers that drop you into it (complete concentration, novelty, risk, the challenge-skills sweet spot) and why the best creative work tends to happen when you stop trying to focus and start building the conditions where focus is inevitable.

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Pretty Fly Copy

BIC

Format: Ad
Spotted By: The Ads Professor
Why I like it: Another example of how words and images can work together. Without the image, the words make no sense. Without the words, the image has no context.

STILL HERE

Format: Email
Why I like it: This didn’t feel like an email campaign – it felt more like a snippet out of a magazine. I also loved the social proof piece and how it was story-led. Wonderful!

COLUMBIA

Format: Email
Why I like it: Subject line = 🔥 But also goes to show that a headline and sub-headline are all that you need for a good apparel email.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Marketing Manager

• Senior Copywriter

• Group Copy Supervisor

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

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Welcome to the 126th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: There’s a line between persuasion and manipulation.

• AI Tip: Your Project knowledge base is only as good as what you leave out.

• How to Rot Your Brain with AI (via Ruben Hassid)

• No, a headline tweak won’t fix your differentiation problem (via Diane Wiredu)

• You’re Wasting Your Highest-Intent Shoppers (via Eli Weiss)

• Podcast Pick: How to Influence & Sell to Anyone Using Imagination (via Joanna Wiebe)

• Swipe File Additions

• Job Opportunities (it’s back!)

Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

There’s a line between persuasion and manipulation.

Too many copywriters and marketers don’t know where it is.

Persuasion helps someone see a real problem (and the path forward) more clearly. Manipulation exaggerates, distorts, or invents one.

Persuasion says: here’s what’s actually at stake, and here’s how this helps.
Manipulation says: things are worse than they are, and you’re running out of time.

The reason this matters isn’t just ethical, it’s practical. Manipulation might convert once. But it attracts the wrong customers, potentially spikes refunds, and quietly destroys trust in your brand.

Good copy doesn’t manufacture urgency. It reveals it.

If the problem is real and your product actually solves it, you don’t need to exaggerate anything. Just make it clear.

AI Insight of the Week

Your Project knowledge base is only as good as what you leave out.

Your instinct is probably to upload everything. Brand guidelines, tone docs, past campaigns, product specs, competitor research, etc.. You think, more context feels like better context.

But… it isn’t.

Claude pulls from everything in that knowledge base when it responds. EVERYTHING. Bloat it with tangentially relevant material and you dilute the signal. The important stuff has to compete with everything else you threw in.

Think of it like onboarding a new hire. You don’t hand them every document the company has ever produced. You give them what they need to do the job well, and nothing more.

For most Projects, that’s three things: who the brand is, who the customer is, and what good output looks like.

Everything else is noise until proven otherwise.

Must-Read Articles

How to Rot Your Brain With AI (via Ruben Hassid)

Why I recommend it: You can outsource your thinking to AI, but you can’t outsource your understanding. Ruben Hassid walks through his full 5-step workflow — from loading real context to treating Claude’s first draft like a junior intern’s work — and makes the case that if you finished an AI task in two turns, you stopped too early.

No, a headline tweak won’t fix your differentiation problem (via Diane Wiredu)

Why I recommend it: Most “copy problems” are messaging problems, and most messaging problems are positioning problems. Diane Wiredu makes the case that differentiation doesn’t live in a tagline, it lives in the gap between what you think makes you special and what your customers actually value.

You’re Wasting Your Highest-Intent Shoppers (via Eli Weiss)

Why I recommend it: Three flows and a welcome series is not a retention program. Eli Weiss breaks down why most brands’ email revenue is propped up by one flow while the rest of the lifecycle sits empty, and why lazy discounting trains your best customers to wait you out instead of buy.

You Should Read This Too:

JOANNA WIEBE
How to Influence & Sell to Anyone Using Imagination
Watch on YouTube

Why I recommend it: Five frameworks for living in your customer’s imagination — from flipping the status (Nespresso didn’t make better coffee, they made you feel better for choosing it) to giving them a superpower (Stripe didn’t sell payments, they sold “you can build now”). Each one works by changing how the customer sees themselves, not how they see your product.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

PLUTOTV

Format: Email
Why I like it: Two things I enjoyed about this email: 1) The hero’s image + headline pair; and 2) the CTA button for the X-Files module.

ROBBINS

Format: Sign
Spotted By: Jade Trott and Lee Trott
Why I like it: A great glimmer of a brand’s personality in action. It doesn’t take much to surprise and delight your reader – just intention (and bravery).

HISCOX

Format: Ad
Spotted By: Vikki Ross
Why I like it: Yeah, it’s hard to read, but it sure does stand out compared to everything else next to it. Next time you’re writing a subject line for an email or an ad for Meta, think about what everyone else’s creative is going to look like – then do the opposite.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Email Marketing Specialist

• Digital Marketing Specialist

• Senior Copywriter

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

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Welcome to the 125th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Your copy isn’t just your words.

• AI Tip: Voice-to-text + Claude

• What does writing with AI actually feel like? (via Psychology Meets Writing)

• Suggest Practical Items to Reduce Cart Abandonment (via Science Says)

• Your Users Give You 30 Seconds: Here’s How to Make Them Count (via OneSignal)

• Podcast Pick: How to Generate Your Best Ideas (via Simon Sinek)

• Swipe File Additions

Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Your copy isn’t just your words…

It’s how fast you respond to a support ticket.
It’s the font you chose.
It’s the placeholder text in your form fields.
It’s whether your 404 page sounds like a human or a legal department.

Every element of your brand communicates something. None of it is neutral.

That’s what “Everything Speaks” means. And most brands only think about copy when someone’s actually writing words, which means they’re ignoring 80% of what’s actually being communicated.

Your customers don’t separate “the design” from “the message.” They experience all of it as one thing. And they form an opinion about who you are based on all of it.

So the question isn’t just what does our copy say?

It’s what does everything say?

AI Insight of the Week

Voice-to-text + Claude is the fastest ideation loop most people haven’t tried.

Typing slows thinking. You edit as you go, second-guess word choices, and lose the thread. By the time the idea hits the page, it’s already been filtered.

That’s not *always* bad, but it is slower.

Voice doesn’t do that. You talk the way you think — messy, fast, associative. The idea stays intact.

Dictate into your phone, drop the transcript into Claude, and tell it to pull out the core idea, clean up the structure, or turn it into a draft.

You’ll go from raw thought to usable output in minutes without the friction of a blank page.

It’s not really a writing hack. It’s a *thinking* hack that happens to create a workable first draft.

Must-Read Articles

What does writing with AI actually feel like? (via Psychology Meets Writing)

Why I recommend it: A grieving writer couldn’t find the words for nine stories until she started writing alongside GPT-3. By the ninth draft, only two lines belonged to the AI. The follow-up to the MIT study piece, this one explores “rhetorical load sharing” and why your writing with AI will only ever be as good as you.

Suggest Practical Items to Reduce Cart Abandonment (via Science Says)

Why I recommend it: A cart full of fun purchases triggers guilt, and guilt triggers abandonment. Recommending one or two practical items alongside indulgent ones reduced cart abandonment by up to 21%. Based on 14 million ecommerce sessions, not guesswork.

Your Users Give You 30 Seconds. Here’s How to Make Them Count. (via OneSignal)

Why I recommend it: Your users open the app for 30 seconds between meetings… not for a 12-step onboarding tour. This is a practical walkthrough of “micro-journeys”: short, cross-channel sequences where every single touchpoint stands on its own and delivers value even if it’s the only one they see.

You Should Read This Too:

SIMON SINEK
How to Generate Your Best Ideas
📼 Watch on YouTube

Why I recommend it: Ask for 15 ideas in 48 hours — because the first three or four are obvious and the eleventh, twelfth, and thirteenth are where the real gold lives. Simon Sinek walks through his “dog pile” brainstorm method: no judgment, no senior leaders in the room, and a green/yellow/red sort that gets the best ideas into execution fast.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

AIR TRANSAT

Format: Ad
Spotted By: Joel Holtby
Why I like it: The power of comparison on full display.

BELLROY

Format: Email
Why I like it: I know I’ve been featuring Bellroy quite a bit lately, but this is a powerful campaign where they leverage the power of affirmations in such a way that it positions their products as a central role in each one. I wish I had thought of this…

GORUCK

Format: Email
Why I like it: Another that I’m sorry for including so frequently here, but whoever’s taken over GORUCK’s email program is killing it with story-based campaigns. This one shows how a 3-star review led to an entire pivot within a product line.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

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Here’s how most burnout conversations go.

Someone on the team starts missing deadlines. Or they’re delivering work that feels hollow. Or they’re just quieter than usual, grinding through their days without much of the spark that made them good at this in the first place.

And the response, more often than not, is to treat it as a personal problem.

Rest more.
Set better boundaries.
Practice self-care.

As if the right morning routine could fix a fundamentally broken workflow. But that’s the wrong diagnosis, and a wrong diagnosis leads to the wrong cure.

Burnout isn’t usually a discipline problem. It’s a design problem.

And the reason that distinction matters so much is this: if burnout lives in the design, then fixing it requires looking honestly at the design — who built it, who maintains it, and who has the authority to change it.

That answer is more distributed than most people want to admit.

The System Nobody Designed for Sustainability

Most creative workflows weren’t built with creative capacity in mind… they were built for throughput.

Speed. Volume. Get it out the door. More drafts, faster reviews, tighter turnarounds. Not to mention, the metrics that get tracked are almost always about production, rarely about the conditions that make good production possible.

So creatives end up working inside systems optimized for output, not for the kind of deep, focused thinking that actually produces strong work.

They’re constantly context-switching between projects. They get feedback late, which means they rework things they already finished. Priorities shift mid-sprint. The brief arrives incomplete, and yet the deadline doesn’t move.

None of that is a personal failure. It’s a structural one.

The person who burns out inside that system isn’t weak, they’re just human! And humans aren’t designed to do their best creative work under sustained, low-grade chaos. Nobody is.

So before you reach for a personal solution to what might be a systemic problem, it’s worth asking: what exactly is the design doing here?

What the Senior Copywriter Actually Owns

Senior copywriters have more agency over their situation than they typically claim (that’s not a criticism — it’s just true). But with that agency comes real accountability.

You own your time architecture. When you do deep work, when you batch feedback reviews, when you protect the two hours in the morning where you actually think clearly — that’s yours to design. Nobody is going to do it for you, and waiting for permission is a strategy for staying stuck.

You own your creative standards. That means saying no (or at least saying “not yet”) to work that doesn’t have what it needs to be done well. No clear brief? No defined audience? No realistic timeline? Accepting that work anyway and then quietly struggling through it isn’t professionalism. It’s a slow leak.

And if you manage juniors, you own your influence on them more than you probably realize. The habits you model, the norms you tolerate, the standards you hold — those become the water juniors swim in. They’re learning from you whether you’re teaching intentionally or not.

But if you’re consistently overextended and you haven’t said anything to anyone, you’re just participating in the conditions that are wearing you down. That’s not blame. Again, it’s the truth. But there is a real difference between blame and ownership. Ownership just means you have more leverage than you’re using.

AI is genuinely useful here, by the way. Research, first-pass variations, reformatting, summarizing briefs — these are tasks that eat real time without requiring your best thinking. Building AI into your personal workflow intentionally creates breathing room for the work that actually needs you. But you have to build it in. It won’t happen by accident.

What the Leader Actually Owns

Leaders don’t just assign work, they also design the environment work happens in. And that’s a much bigger responsibility than most of them are walking around with.

Workload visibility is on you. Not what’s been assigned, but what’s actually on your team’s plate. Those are often very different numbers (and if you don’t know the difference, you’re managing a spreadsheet, not a team).

Priority discipline is on you. Every last-minute request that lands on your team’s desk without a corresponding removal from their list is a choice you’re making, even if it doesn’t feel like one. Scope creep doesn’t just happen. It’s allowed to happen.

Feedback quality is on you. Vague feedback creates rework. Late feedback creates invisible overtime. If your team is regularly reworking things they thought were done, that’s not a creative problem — it’s a process problem, and it lives upstream of the creative.

Recovery time is on you. Not just between big projects, but within them. The assumption that creatives will naturally recharge between sprints is almost always wrong, especially inside organizations that treat every quiet moment as an opportunity to add more to the pile.

The most common leadership failure in creative environments isn’t malice. It’s assumption. Assuming people are fine. Assuming strong work means strong capacity. Assuming that because no one has complained, everything must be working.

A leader who doesn’t actively protect creative capacity is passively eroding it. That’s not a harsh statement. It’s just how systems work.

AI can help here too — workflow data and simple tracking tools can surface overload signals well before they become burnout signals. But the data only matters if someone with actual authority looks at it and does something.

Where These Two Things Meet

You can build a genuinely thoughtful personal system and still burn out inside a broken organizational one.

A leader can design a genuinely supportive environment and still watch someone burn out because they never learned to protect their own time or ask for what they need.

Both are real. Both happen regularly. And this is exactly why individual solutions and systemic solutions have to coexist. Neither one is sufficient on its own.

For senior copywriters who manage juniors, you’ve felt what a broken system does to a person. You know what it costs. You also have a hand (maybe a larger one than you think) in shaping what your juniors experience day to day.

That’s not a small thing. It’s actually kind of a significant one.

The goal isn’t to make everyone maximally productive, it’s to build conditions where people can do genuinely good work without quietly paying for it in ways nobody tracks.

The Reframe

Burnout isn’t a sign that someone isn’t tough enough.

It’s a signal that the design failed somewhere. The question worth asking isn’t “why can’t this person handle it?” It’s “what in the system made this inevitable, and who had the authority to change it?”

Usually, the honest answer points in more than one direction.

So here’s where to start.

If you’re a senior copywriter: what’s one part of your workflow you’ve been tolerating that you actually have the authority to change?

If you lead creatives: when did you last ask your team what they need to do their best work — and actually change something because of the answer?

Pick one. Start there.

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Welcome to the 124th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Structure vs. Style

• AI Tip: Prompts = Assets

• Show Your Marketing Boss Who’s Boss with Email Opt-Outs (via CMSwire)

• Signposting: How to Reduce the Cognitive Load of Your Reader (via Wes Kao)

• 4 language psychology secrets from your competitors (via the Growth Tribe)

• Podcast Pick: The New Avatar Framework (How to Build Avatars That Scale in 2026)

• Swipe File Additions

Copy Tip of the Week

A lot of copywriters and copy editors think that “editing” is just making things better.

But too many younger editors only focus what’s on the surface and ignore what’s underneath.

Because what’s underneath is usually harder to fix.

I’m talking about *structure*, and no matter how hard you try, you can’t polish your way out of a structural problem.

If a piece of copy isn’t landing, most writers do what feels productive – they tighten sentences, swap words, add a stronger verb here, and cut a weak adjective there.

And yet, the copy still doesn’t work.

It’s not because the editing is bad. It’s because the problem isn’t in the sentences. It’s in the skeleton underneath them.

Here’s what I mean by skeleton: the logical sequence of your argument. The order in which you introduce the problem, the stakes, the solution, and the proof. Basically, the reason a reader should keep going.

If that sequence is broken, no amount of sentence-level polish fixes it. You’re just decorating a janky frame.

So before you edit a single word, ask: does this move in the right order? Does each section earn the next one? Is the reader being led somewhere, or just standing in place?

If the answer’s no, stop editing and restructure things first.

The words come last.

They always do.

AI Insight of the Week

A great prompt is an asset. Start treating it like one.

Most people write a prompt, get a good output, and move on. The problem is that it disappears into chat history and they rebuild it from scratch next time — slightly different (and slightly worse).

When a prompt consistently works, save it! It encodes your standards, your constraints, your audience context. Everything you’d otherwise re-explain every single time.

Then, keep a running doc of your highest-frequency prompts (e.g., subject line generation, offer angle brainstorming, first-draft briefs, etc.). Write the prompt once — *carefully* — and save it.

Worth capturing alongside it: what it’s for, what model it performs best on, any negative constraints that make it sing. Basically, treat it like a SOP.

A prompt you refine once and use weekly pays back every week.

Must-Read Articles

Show Your Marketing Boss Who’s Boss with Email Opt-Outs (via CMSwire)

Why I recommend it: Less than 1% of your list will opt out of Mother’s Day emails — but some of them are your highest-LTV customers. Chad White walks you through the exact conversation to have with your boss about why giving subscribers the choice protects revenue, not costs it.

Signposting: How to Reduce the Cognitive Load of Your Reader (via Wes Kao)

Why I recommend it: Your reader shouldn’t have to finish a sentence to know why it matters. Wes Kao breaks down “signposting” — starting sentences with phrases like “the surprising thing is…” or “the most important part to keep in mind is…” — so your reader’s brain can organize information as it arrives, not after.

4 language psychology secrets from your competitors (via the Growth Tribe)

Why I recommend it: Four language psychology principles that should govern every word across every channel — from the Pratfall Effect (why admitting a flaw builds trust) to Negation Blindness (why “no hidden fees” makes people think about hidden fees). Research-backed, example-heavy, and directly applicable to your next email or landing page.

You Might Also Like:

BRAIN DRIVEN BRANDS
The New Avatar Framework (How to Build Avatars That Scale in 2026)
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: The customer avatar was invented by a software developer who asked “what would Kathy do?” — not “who is Kathy?” Sarah Levinger and Nate make the case for reordering the avatar framework: start with when someone needs you, then why, then who — because a Taco Bell drive-through at midnight has a Bentley and a beat-up Nissan in the same line.

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Pretty Fly Copy

GREATER ANGLIA

Format: Ad
Spotted By: Sam Plant (LinkedIn)
Why he likes it: The best PSA copy doesn’t dress the message up. It finds the smartest, most memorable way to deliver it, without being so smart that it flies over people’s heads.

OLUKAI

Format: Email
Why I like it: Dead simple and I thought it was a joke until I realized it wasn’t.

WHOOP

Format: Ad
Spotted By: The Ads Professor
Why I like it: A wonderful play on lyrics words.

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 123rd edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Simple Sales → Simple Messaging

• AI Tip: Tell Claude What NOT to Do

• Courage vs. excuses (via Seth Godin)

• When many buyer personas push ideal customers away (via Frictionless Growth Lab)

• How to Create Systemic Growth Frameworks on Meta for Confident Scaling (via Foxwell Digital)

• Leading Teams Through Change (via The Copy Minimalist)

• Podcast Pick: Do Marketers Need a Personal Brand?

• Swipe File Additions

Copy Tip of the Week

If your sale requires a spreadsheet to manage, it’s probably already too complicated.

Your customer is experiencing everything about it with fresh eyes. No briefing doc. No Slack thread. Just whatever lands in their inbox or shows up on their screen.

So if they have to stop and think about how the deal works, you’ve already lost ‘em.

In my opinion, the best sales are boring to explain:

• X% off everything

• $X off orders over $X

• Spend $X, get a free gift

Simple offer = simple message = less friction between your customer and the buy button.

Complexity doesn’t signal value. It signals confusion.

AI Insight of the Week

Tell Claude what not to do.

Most prompts are all positive instruction. Write this. Sound like this. Include this. And then the output comes back and something’s off (e.g. too formal, too long, too generic, etc.) and you’re not sure why.

Here’s why: positive instructions tell Claude what to aim for. But they don’t rule out everything that misses the mark.

You asked for “conversational” and got “casual.”
You asked for “concise” and got “short but hollow.”

The instruction was followed.
The intent wasn’t.

Negative constraints, however, will help close that gap.

“Don’t use bullet points.”
“Don’t open with a question.”
“Don’t explain what you’re about to do — just do it.”

These aren’t just stylistic preferences, but guardrails that eliminate the most common failure modes before they happen.

The underlying principle: Claude is trying to satisfy your prompt, not read your mind.

A prompt with clear negative constraints is a tighter brief. And tighter briefs produce better work, whether you’re directing Claude or a copywriter.

Must-Read Articles

Courage vs. excuses (via Seth Godin)

Why I recommend it: “AI” has become a two-letter excuse for averaging everything down. Seth Godin’s short reminder that excellence is scarce precisely because excuses are abundant — and that knowing your purpose is what makes courage findable.

When many buyer personas push ideal customers away (via Frictionless Growth Lab)

Why I recommend it: A billion-dollar brand had to reshoot an entire ad because the buyer persona wasn’t deep enough to brief the creative team accurately. If your personas are vague, everything downstream (briefs, copy, campaigns, etc.) quietly excludes the people you’re supposedly trying to reach.

How to Create Systemic Growth Frameworks on Meta for Confident Scaling (via Foxwell Digital)

Why I recommend it: Most Meta scaling problems aren’t ad problems — they’re margin problems. If your AOV can’t support the auction, no amount of budget increase will fix your CAC. A thorough breakdown of the math, creative diversification, and campaign structure behind scaling that actually holds.

You Might Also Like:

TALKING TOO LOUD w/ Chris Savage
Do Marketers Need a Personal Brand (feat. Carmen Vicente)

🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: At some point, doing your job stopped being enough — now you’re expected to be the brand too?! Carmen Vicente breaks down why personal accounts outperform company pages by 40x, why your flops are a sign you’re testing enough, and what to do if you don’t want to become a content creator but can’t afford to be invisible.

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Pretty Fly Copy

GORUCK

Format: Email
Why I like it: They’ve been on a roll lately with great emails. But I loved the narrative/identity-driven approach to this. Shows how the product works into everyday life without being overwhelming. The family pic helped. Also, the CTA slaps.

THE COLLECTIVE

Format: Billboard
Spotted By: Ben Bailey
Why he likes it: “If you fancy yourself as a copywriter you should study this ad. Ernest Hemingway was reported to have once been asked to write a story in six words or less - this ad manages it in three.”

UNKNOWN

Format: Advertisement
Spotted By: Jade Trott and Lee Trot
Why I like it: One horrific word can make or break an advertisement.

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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How your team operates will change this year.

Maybe it already has. A new platform… a new process… a directive from above that everyone needs to get comfortable with about something nobody fully understands yet.

And if you watch closely when that happens, you’ll notice something that doesn’t get talked about much.

Your strongest people grow quiet.

Not because they’re disengaged or don’t want to learn, but because they’ve spent years building something that matters to them — a standard, a reputation, an instinct that other people rely on — and suddenly they’re a beginner again.

Despite what it looks like on the surface, it’s not resistance. It’s actually something more human than that.

What Change Actually Threatens

Here’s the thing a lot of folks get wrong about creative professionals, and it’s something that separates them from most other knowledge workers.

Their competence is their identity.

A senior copywriter doesn’t just do good work.
She is someone who does good work.

That distinction lives in how she carries herself in a brief, how she gives feedback, how the junior writers watch her work and try to reverse-engineer what she does naturally.

Introduce a new tool… and that identity gets temporarily destabilized.

The junior who had nothing to prove picks it up over a weekend and suddenly looks more capable than the person who’s been here for 8 years. And the hierarchy that everyone understood (even if no one ever named it) gets flipped.

The senior writer knows it.
She can feel it.

And what looks like resistance is usually this: a rational response to a status threat. The person isn’t saying “I don’t want to learn.” She’s saying, “I don’t want to look incompetent in front of the people I’ve been leading.”

Leaders who miss this spend all their energy on the tool. They run demos. They share tutorials. They talk about efficiency gains and workflow improvements.

None of that touches the actual problem.

(Can you tell that I’m kinda talking about AI yet?)

Your Job as a Leader Isn’t Change Management

Honestly, “change management” is a corporate concept. It treats people like variables that need to be aligned to a new configuration.

That’s not what’s being asked of you here (it lacks empathy anyway and I’m not an unempathetic guy).

What’s being asked is harder and more specific: create enough safety for your team to try something they might fail at, without that failure meaning something about their worth.

And you know what? That starts with you.

If you’re rolling out a new tool or process you haven’t fully figured out yet, say that! Don’t “perform” confidence you don’t have. Your team will see through it immediately, and the gap between what you’re projecting and what’s actually true will cost you more trust than the uncertainty itself.

Model the learning out loud. Let them watch you struggle with something. Ask questions in the room instead of only behind closed doors. When you make the beginner visible — when you show that even you haven’t figured this out yet — you give everyone else permission to be figuring it out too.

Make the try-and-fail window explicit. Don’t assume people know they’re allowed to be bad at something before they’re good at it. Say it!

“For the next month, we’re learning. Nothing we produce in this context is going into a performance review. We’re just figuring out what this does and doesn’t do for us.”

Assumed safety isn’t safety.
Named safety is.

Does your team actually believe they’re allowed to struggle with this in front of you? Or do they feel like they’re supposed to have it figured out already?

If the answer is the latter, you haven’t created a safe space yet. Get to work.

Pilots = Signals

The reason low-stakes pilots work isn’t really about the stakes.

It’s about the signal.

When you set up a pilot — a real project, real work, but not a client deliverable riding on the outcome — you’re telling the team: this is learning time, not performance time. That distinction matters more than any tutorial you could run.

The structure doesn’t need to be complicated. Give the team a genuine brief. Run it with the new tool or process. Then sit together and look at the results.

Not to evaluate who got it right but rather to figure out what the experience actually was.

What worked?
What slowed people down?
Where did the new approach help the thinking, and where did it get in the way of it?

That debrief is the point. The output is secondary.

And at the end of it, ask each person something simple: one thing that felt useful, one thing that felt off. That’s not data collection. That’s a leadership act. It tells your team that their experience of the change matters to you, not just the outcome.

That’s different from most rollouts. Most rollouts ask people to adapt and then measure whether they did. This one asks people to think and create alongside you.

And honestly? That sense of shared ownership creates buy-in like no other.

What To Say (And What Not To)

Most leaders undersell the difficulty and oversell the benefit. But what actually builds trust during change is specific and honest, not positive and vague.

Name what’s changing.
Name what isn’t.
And name what you don’t know yet.

Before you make any announcement, ask yourself one question: am I framing this for them, or for me?

If the answer is for you — to look decisive, to project control, to manage up — the framing will land hollow. People can feel the difference between a leader who is leveling with them and a leader who is managing them.

Level with them.

The Part No One Talks About

Some people on your team won’t adapt the same way. And a few of them won’t actually be resisting. They’ll have a legitimate case.

A writer who has spent 15 years in direct response, who has built a process that produces reliably strong work, may find that certain new tools actively interrupt how she thinks. The friction isn’t stubbornness. It’s craft.

Your job is to know the difference, and I argue, respect the difference.

The question isn’t “is this person resisting?” It’s “does this new approach actually serve the work they’re doing?” Those are different questions with different answers.

Good leaders leave room for that distinction. They don’t mistake uniformity for alignment. A team that has genuinely evaluated a new tool and reached different conclusions about how to use it is a healthier team than one where everyone adopted it on the same timeline because that’s what was expected.

The goal isn’t consensus on method. It’s shared commitment to the standard.

The Tools Will Keep Changing

They always do.

Something will come out next year that makes the current conversation feel dated. Your team will be asked to learn it, adapt to it, and eventually become fluent in it.

What won’t change is this: your team is made up of people who built their careers on being good at something. Every time the ground shifts, that competence feels briefly at risk.

Your job isn’t to manage that away.
It’s to hold the space while they find their footing again.

New tools.
New trends.

Same humans.
Same job.

Further Reading

For leaders who want to go deeper on the human side of change. Curated for creative leaders — not enterprise change managers.

Managing Transitions: Making the Most of Change — William Bridges & Susan Bridges The clearest book on why change is hard even when people want it. Bridges separates the external event from the internal psychological reorientation — and argues it’s the transition that leaders almost always undermanage. Start here.

Switch: How to Change Things When Change Is Hard — Chip Heath & Dan Heath Change fails not because people are stubborn, but because leaders appeal to the rational mind and ignore the emotional one. Practical and human.

Dare to Lead — Brené Brown Specifically useful here for its research on psychological safety and vulnerability in leadership. The chapters on trust and learning cultures map directly to what this essay is about.

Leadershift — John Maxwell Focused on the internal shifts leaders need to make before they can lead others through change. Useful if you’ve ever wondered why your team isn’t following you when you feel like you’re doing everything right.

The Fifth Discipline — Peter Senge A slower read, but foundational. Senge’s concept of the learning organization asks: how do you build a team that can adapt without breaking? Worth the time if you’re thinking long.

HBR’s 10 Must Reads on Change Management — Harvard Business Review A survey of the field’s core frameworks without committing to one author’s worldview. Good desk reference if you want range before you go deep.

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Welcome to the 122nd edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Emotional Language vs. Emotional Truth

• AI Tip: 3 Questions to Answer for Project Instructions

• The Post-Purchase Moment Where Loyalty is Won or Lost (via MarTech)

• Pilcrow – Design Story (via Umbrik Journal)

• Handmade Designs: The New Trust Signal (via NN/Group)

• Podcast Pick: AI & Your Career (Think Fast, Talk Smart)

• Swipe File Additions

Copy Tip of the Week

“Heartfelt.”
“Unforgettable.”
“Life-changing.”

These words are trying to feel emotional.

They don’t.

There’s a difference between emotional language and emotional truth — and most copy gets it backwards.

Emotional language reaches for feeling-adjacent words. Words that signal emotion without actually creating it. “Heartfelt” doesn’t make anyone feel anything. It just points at the idea of a feeling and hopes the reader fills it in.

Emotional truth is different. It’s specific. It’s a moment the reader has actually lived — the 2am scroll before a big decision, the way a product smells like something familiar, the relief of finally not having to think about it anymore.

One describes a feeling. The other triggers it.

The principle: specificity is what creates resonance, not vocabulary.

So next time you reach for an emotional word, stop and ask: what’s the actual moment? Write that instead.

AI Insight of the Week

Your Project system prompt should answer three questions.

Most people write their Project system prompt like a job posting. A list of instructions. A few tone descriptors. Maybe a note about what to avoid.

That’s not enough.

A system prompt is the difference between a specialist and a generalist. And the gap between them isn’t instructions — it’s the context.

Claude doesn’t just need to know what to do. It needs to know who it is, who it’s talking to, and what a good output actually looks like.

Those three questions:

1. Who is Claude in this Project?
   Not just a role — a point of view. A senior conversion copywriter thinks differently than a brand strategist. Define the lens, not just the title.

2. Who is Claude writing for?
   Your audience’s awareness level, sophistication, objections, language. The more specific this is, the less you’ll spend correcting outputs that are technically correct but tonally wrong.

3. What does good look like?
   Give Claude an example of your best work — not average output, your best. That’s the bar it’s calibrating to.

Answer all three and your Project stops feeling like a tool you’re fighting and starts feeling like a team member who actually gets it.

Must-Read Articles

The Post-Purchase Moment Where Loyalty is Won or Lost (via MarTech)

Why I recommend it: Your order confirmation email isn’t just operational — it hits right when the buyer’s brain shifts from excitement to doubt. Kath Pay breaks down four buyer modalities and how a single post-purchase email can reassure all of them without heavy segmentation.

Pilcrow – Design Story (via Umbrik Journal)

Why I recommend it: The ¶ symbol started as a paragraph marker, was hand-drawn in red ink by medieval rubricators, and got killed off when the printing press moved too fast for anyone to draw it. A short, nerdy origin story for a character you’ve seen a thousand times without knowing its name.

Handmade Designs: The New Trust Signal (via NN/Group)

Why I recommend it: When anyone can generate a polished image in minutes, polish stops being a quality signal. NN/g breaks down why handmade imperfection — in visuals and in voice — is becoming the new trust signal. The same logic applies to copy: if it sounds like a person wrote it, people believe a person cares.

You Might Also Like:

The Copy Minimalist

You Can Scale a System. You Can’t Scale Chaos.

Something strange happens when an agency starts growing…

Read more

4 months ago · 2 likes · Matt Snyder

THINK FAST TALK SMART
AI & YOUR CAREER
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: 70% of the average skills in your job will change by 2030 — and you get to decide how. Former Obama speechwriter Aneesh Raman breaks your work into three buckets (what AI can do, what you do with AI, and what only humans do) and makes the case that curiosity, creativity, and communication are the career moat.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

GORUCK

Format: Email
Why I like it: A great example of taking a core customer complaint with your competitors, amplifying it, and then demonstrating how your version of the product is different. Using negative competitor reviews from Amazon? Brilliant.

BUNNAHABHAIN

Format: Billboard
Why I like it: What’s something your customers always get wrong about your product? Well, turn it into a billboard (or a headline) that frames it differently.

LAPHROAIG

Format: Email
Why I like it: Sometimes respelling words is a great way to integrate your brand voice and identity into a rather unspectacular sentence. That’s what Laphroaig did here (”unphorgettable”).

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 121st edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: You can’t persuade someone who isn’t paying attention

• AI Tip: Ask Claude to rewrite your copy at 3 different awareness levels.

• 9 Ways to Improve Marketing Messaging Performance (via Zeta Global)

• Customer messaging playbook: 7 trends to act on now (via Customer.io)

• How to Send Fewer Emails and Get Better Results (via One Signal)

• I wrote this for you (via The Copy Minimalist)

• Podcast Pick: Why Earning Trust Beats Clicks in Modern Marketing (with Amanda Natividad)

• Swipe File Additions

Copy Tip of the Week

You can’t persuade someone who isn’t paying attention.

Sounds obvious, but watch how most copy is actually written.

The offer shows up in sentence two.
The benefit is buried in paragraph three.
The CTA arrives after three sections of features nobody asked about.

That’s not a writing problem, but rather a sequencing problem.

Attention is a prerequisite to communication – not a given, and it doesn’t hold indefinitely. Every sentence either earns the next one, or it doesn’t. The moment you lose someone’s attention, the rest of your copy doesn’t exist.

This is why the best copywriters think about order as much as content. What you say matters, but when you say it matters more.

The principle: Attention Precedes Action.

Earn the read before you ask for the click.

AI Insight of the Week

Ask Claude to rewrite your copy at 3 different awareness levels.

Most copy fails before the first word lands because it assumes the reader knows more than they do.

Eugene Schwartz mapped this out decades ago: your prospect exists somewhere on an awareness spectrum, from completely unaware of their problem to ready to buy.

Where they sit determines what your copy needs to say first. Get it wrong and it doesn’t matter how good the writing is.

Here’s the move: take a draft you’ve written and ask Claude to rewrite it at three awareness levels — Unaware, Solution-Aware, and Most Aware. Don’t just collect three variants. Study what changed!

It shows you what assumptions you baked into your original and whether you’re actually meeting your reader where they are, or where you wish they were.

Most of the time, you’ll find your draft skews later in the awareness spectrum than your actual audience sits.

And that’s the gap that could be costing you conversions.

Must-Read Articles

9 Ways to Improve Marketing Messaging Performance (via Zeta Global)

Why I recommend it: Your email, SMS, and push messages aren’t the destination — they’re the door. Nine practical rules for writing marketing messages that earn the click: follow the Rule of One, design for scanning, use microcopy over full sentences, and make every word accountable to the outcome.

Customer messaging playbook: 7 trends to act on now (via Customer.io)

Why I recommend it: Seven shifts reshaping customer messaging in 2026 — plain text beating designed emails, behavioral triggers beating demographics, conversion metrics beating opens — each paired with specific AI prompts and tactics you can test this week.

How to Send Fewer Emails and Get Better Results (via One Signal)

Why I recommend it: Not every message belongs in email — but when email is your only channel, everything gets forced into the inbox whether it fits or not. This presents a simple framework for deciding what actually belongs in email vs. what should move to push, SMS, or in-app, so the emails you do send earn their place.

You Might Also Like:

Talking Too Loud
Why Earning Trust Beats Clicks in Modern Marketing (with Amanda Natividad)
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: The internet has shifted from a click-through environment to in-platform consumption — but most marketers are still optimizing for the click. Amanda Natividad of SparkToro breaks down why the best content now earns trust, recall, and preference without needing the click to prove it worked.

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Subscribe here to unlock the magic link.

Pretty Fly Copy

GORUCK

Format: Email
Why I like it: Raising your prices is never easy, especially when you already make a premium product. But I thought GoRuck handled this well. It gave people a glimpse inside of how their business operates, which explains the why behind price increases.

DOMINOS

Format: Ad
Spotted By: The Ads Professor
Why he likes it: They saw a competitor headline and flipped it in real time. Same format. New punchline. No new creative needed. Just speed and awareness.

VIRGIN ATLANTIC

Format: Email
Why I like it: Virgin’s copy across the board is always entertaining and lighthearted. On my recent overseas flight, this was the email confirmation I received after making my meal option. “nom nom nom”.

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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After spending the last two weeks offline and completely disconnected from the internet, I returned back to my routine and rhythm with a renewed perspective.

While I recognize the value (and sense of disruption) evolutions like AI brings to my industry, I also recognize the importance of authenticity and human connection.

So, I wanted to find a way to signal that across my online real estate.

I’ve decided to make the “Copywriter Column” more personal, and I’m bringing it exclusively to the inbox.

These will be short and unfiltered thoughts on topics and trends and insights in marketing. I’m committed to handwriting these first, so you’ll know they’re genuine and really from me.

The in-depth articles and insights I’ve typically leveraged the Copywriter Column for are getting a new home: The Edit.

I have a lot of topics already planned out for this year, but always welcome for suggestions. That said, I want to move away from only writing on “copywriting” and expand The Edit to also include topics around broader messaging strategies and creative team management and leadership. They’ll remain grounded in sound principles – no worries there.

The Weekly Round Up will not change. Although, I will be opening those up to sponsorships soon (stay tuned).

As I progress in my career and life, I’m growing more comfortable with moving a bit slower and not joining the mass frenzy toward every new and shiny object in our space.

I have an affinity toward the more timeless and simple things – ones that have proven themselves over the decades. That includes using a physical pen to put my words and thoughts on actual paper.

So, what’s next?

Well, nothing really changes for you. If you want to receive my Copywriter Columns, you have to sign up here (if you’re not a subscriber already). Everything else really stays the same.

I will say, The Edit will likely take a bi-weekly cadence now, but that’s it.

See you around!
Matt

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The Copywriter Column is a weekly glimpse into the mind of an agency copywriter. Thinking about subscribing? Here’s what else you can expect.

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Welcome to the 120th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: How to Break the Rules

• AI Tip: When and when not to use Claude Cowork

• Stacked (vs single) discounts work better (via Science Says)

• The Resurgence Of Brand Loyalty (via Branding Strategy Insider)

• The Cheerleader Effect: Why Things Look Better in Groups (and How to Use That in Your Emails)

• The One Thing AI Can’t Learn, No Matter How Good Your Prompts Get (via The Copy Minimalist)

• Podcast Pick: “These two words increased sales by 18%.”

• Swipe File Additions

Copy Tip of the Week

Most copywriters learn the rules.

Great ones learn why the rules exist.

There’s a reason “don’t start a sentence with And” became a rule. It’s because most writers lean on conjunctions as a crutch — stitching together loose thoughts instead of building real momentum.

But once you understand that’s what the rule is protecting against, you can break it intentionally.

And when you do, it hits different.

(See what I did there? Haha)

That’s the whole game though. Rules aren’t arbitrary — they’re guardrails built around a principle. Master the principle, and the rule becomes optional.

Here’s a quick test: next time you’re told a rule in copy (e.g. no passive voice, keep sentences short, always have one CTA), ask yourself: what goes wrong when this rule gets broken?

That answer points back to the principle.

Once you’ve got the principle, you’re not following rules anymore. You’re making decisions.

AI Insight of the Week

Cowork earns its keep on tasks with clear inputs and measurable outputs — research, formatting, drafting, processing, organizing.

Give it a well-defined job and it executes without friction.

But some tasks look like execution and are actually judgment.

Editing for voice. Picking the right angle. Knowing when a draft is done.

Those aren’t steps in a process — they’re the product. Automating them doesn’t save time. It moves the cleanup downstream.

Ask yourself before handing anything to Cowork: Is the value here in completing the task, or in how I think through it?

If it’s the latter — stay in the chat.

Must-Read Articles

Stacked (vs single) discounts work better (via Science Says)

🔗

https://app.sciencesays.com/p/stacked-vs-single-discounts-work-better

Why I recommend it: A 25% discount split into stackable parts (15% sale + 10% coupon) drove nearly 16% higher purchase intent than the same 25% as a single discount. The reason: stacking feels rare, makes shoppers feel smarter, and creates urgency — science you can apply to your next promo structure.

The Resurgence Of Brand Loyalty (via Branding Strategy Insider)

🔗 https://brandingstrategyinsider.com/the-resurgence-of-brand-loyalty/

Why I recommend it: Repeat purchases and true loyalty aren’t the same thing — one is habit, the other is commitment. This makes the case that 10% of your most loyal customers can drive 50% of profits, and why deal-chasing strategies erode the brand equity that gets them there.

The Cheerleader Effect: Why Things Look Better in Groups (and How to Use That in Your Emails)

🔗 https://holisticemailacademy.com/2026/02/10/how-to-use-the-cheerleader-effect-in-email-marketing/

Why I recommend it: Your brain rates things as more attractive in groups than alone — it’s called the Cheerleader Effect, and it applies to your emails too. Group your testimonials, curate product collections, and use team photos instead of solo headshots to subtly boost perceived value and trust.

You Might Also Like:

THE NUDGE PODCAST
“These two words increased sales by 18%.”

🎧 Listen on iTunes | Listen on Spotify
Why I recommend it: A Chinese restaurant chain added two words to their menu and increased sales 18% — no price change, no new product, no redesign. This episode breaks down the social proof principle behind it and how to apply it to your own marketing.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

KULFI BEAUTY

Format: Email
Spotted By: Email Love
Why I like it: The hero makes it almost feel like a UGC ad of sorts, but the flow of the email (build your own lip bag) with a “subscribe & save” callout at the end is brilliant.

BELLROY

Format: Email
Why I like it: Sometimes when you have a product category with too similar products, it’s challenging for your customers to know which is the best for them. The “Packs well for” distinction throughout the campaign is a great way to make it clear.

COOPER TIRE

Format: Headline
Why I like it: What’s not to like?

HOWLER BROS

Format: Email
Why I like it: The CTAs were pretty catchy, but especially the last one as it also conveyed a core (very obvious) difference between their shorts and pants. It made me LOL.

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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I’ve been thinking about this for a few weeks now, and while my thoughts aren’t fully formed on the topic, I thought I’d share where my head’s at anyway. So here it goes.

Yes, you can teach AI to write copy. Good copy, even. You can feed it frameworks, voice guidelines, swipe files, persona docs. You can even build entire skill sets for it.

I know this because I’ve done it.

I’ve sat at my desk and codified the way I think about conversion copy into something a machine can execute on command.

And it works.
It works really well, actually.

So when people ask me what the safety net is for copywriters, I don’t think I can give them the answer many of them want. Because the answer they want is “skill.”

But like I just indicated, skill really isn’t it.

Here’s the thing most copywriters in my industry don’t want to sit with want to ignore.

The frameworks are teachable.
The formulas are teachable.
The editing sweeps, the structure of persuasion, the way you build an argument from a headline down through a CTA.

ALL of it can be transferred to a machine.

Again, I’m not speculating here. I’ve done the transfer myself. I’ve taught other people how to do it. I’ve even been paid to do it for other people.

Our profession’s instinct right now is to defend skill, to say “AI can’t do what I do.”

And I get it. It’s a natural response when you feel threatened but you also don’t quite understand the thing you’re being threatened by.

But again, “AI can’t do what I do” is the wrong argument, and it loses every time someone runs a side-by-side and can’t tell the difference.

My advice? Stop defending skill. It was never the differentiator.

So, what is?

In the copy-sphere I operate inside of, the goal of much copywriting is to get a conversion. A client sends an email to customers, and in return, they want customers to click links and buy products.

But getting customers to buy isn’t that easy because buying is not a logic problem.

I know we talk about it like one. We talk about objection handling and feature-benefit alignment and value stacking. And all of that matters at a structural level.

But the moment someone actually decides to buy? That’s not logic. That’s emotion, rationalized after the fact.

The copy that converts doesn’t inform the reader. It resonates with them. It meets them inside a feeling they haven’t quite named yet and says it back to them in their own language.

And that kind of resonance doesn’t come from research.
It doesn’t come from a persona brief or a customer interview transcript.

It comes from having been there.
Having felt the thing.

Not studied it.
Lived it.

Because there’s a gap between “knowing about” a feeling and “having felt it.” And that gap is the entire distance between copy that describes and copy that converts.

Enter, AI…

In this scenario, AI has a knowledge gap. Granted, that one’s closeable. Better prompts, better context, better inputs. You can close it with effort, and it’ll shrink over time.

But AI also has what I’d call a category gap, and unfortunately for it (and every other broccoli-haired writer who lacks a heartbeat), that category gap doesn’t close with better prompts or more data.

Not… ever.

AI has never wanted something badly.
Never felt the specific embarrassment of a problem you’re too ashamed to Google.
Never sat next to someone you love and watched a sunset and felt, in your chest, that time was running out.

That’s not just a limitation of the model.
It’s a limitation of the medium.

AI can replicate the structure of persuasion, but it cannot replicate the origin of it, which is a human being who has wanted something badly, been afraid of something real, and felt the gap between where they are and where they want to be.

This matters most at the conversion layer. I want to be specific about that.

I’m not talking about blog content or SEO pages or product descriptions. Those layers have already been repriced. A lot of what passed for “copywriting” was really just information assembly anyway. For good or ill, AI is better at that. Fine.

The conversion layer is different though. It’s the copy that sits at the moment of decision. The last few seconds before someone either commits or bounces.

And that’s where emotional authenticity does the most work. That’s where a reader needs to feel like the person who wrote the thing gets it.

Anyone can write a feature list. But the writer who converts is the one who names the feeling the reader hasn’t named for themselves yet.

And you can only do that if you’ve felt it. Not studied it. Not researched it. Felt it. In your body. In your memory.

The “riches” aren’t in the “niches.”
They’re not even just in the conversion layer.

They’re in the human being with breath and a heartbeat at the conversion layer.

So, yeah. Skill is one thing. But the lived experience is a whole other.

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Seasonal copy falls flat when writers skip the fundamentals.

The Copy Principles Swipe File is a reference guide built around the principles that make copy work regardless of the season, the campaign, or the brief.

Not tactics. Not templates. The underlying thinking that drives copy that actually connects.

If you want copy that has real weight to it, start here.

Download for Free

The Copywriter Column is a weekly glimpse into the mind of an agency copywriter. Thinking about subscribing? Here’s what else you can expect.

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Welcome to the 119th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Stop trying to write clever copy.

• AI Tip: Start a fresh chat more than you think you should.

• Why Consumers Say Yes to the Product (via KnoCommerce)

• Empowering Women in Marketing: A Leadership Q&A with Lexi Clarke

• Mining Customer Reviews for Content Creation using a Custom GPT (via WTS)

• Podcast Pick: Say What Sticks: The Neuroscience of Memorable Communication feat. Carmen Simon

• Swipe File Additions

Income stuck even though you’re hustling harder than ever?

My friend Scott Mills created a handy guide to help solopreneurs add a minimum of 34% to their income. The secret? It has NOTHING to do with marketing or sales “tactics”.

🚀 Get Unstuck w/ This FREE Guide

Copy Tip of the Week

Stop trying to write clever copy.

Start mining your reviews, support tickets, and Reddit threads for the exact phrases your customers already use.

Then build your headlines, emails, and product descriptions around those words — not yours.

Here’s the principle underneath this ↴

Copywriting isn’t about inventing language. It’s about curating it.

Your reader’s brain is constantly running a background check on everything they read: does this sound like me? Does this person get my problem?

When the answer is yes, two things happen fast: trust goes up and friction goes down. Both of those move people toward a click, a cart, a conversion.

When the answer is no — when your copy sounds like it was written by a marketing department instead of a human who understands the problem — you lose them. Doesn’t matter how polished the headline is.

This is why “use customer language” isn’t just a style tip. It’s a conversion principle. It governs three rules you’ve probably heard before: clarity over cleverness, specificity over vagueness, and benefits over features. All three are downstream of the same idea:

Copy converts when it mirrors how the reader already thinks.

Not when it tries to teach them a new way to think.

Next time you sit down to write, open your VOC data before you open a blank doc. The best copy is already written — you just have to find it.

AI Insight of the Week

Start a fresh chat more than you think you should.

Most people try to fix a drifting conversation by adding more instructions. That’s the wrong move.

Here’s what’s actually happening: Claude reads the entire thread every time it responds. The longer that thread gets, the more your original framing competes with everything that came after it. Drift isn’t a Claude problem — it’s a signal-to-noise problem.

The fix is a fresh chat.

Use a long thread for iteration — when you’re refining the same output. Start fresh when the problem has genuinely changed. A simple test: Could someone reading only your next message understand exactly what you need? If not, you’ve drifted. Reset.

Before you do, run this prompt:

“Give me a context handoff — not a summary of our conversation, but a brief that captures what we’re building, what’s been decided, and what the next step is.”

Paste that into your fresh chat. You get a clean context window and all the signal — none of the noise.

Must-Read Articles

Why Consumers Say Yes to the Product (via KnoCommerce)

🔗 https://knocommerce.com/blog/understanding-customer-spending-motivations/

Why I recommend it: Your highest-AOV customers aren’t motivated by discounts — they’re motivated by trust, transparency, and brand alignment. This breaks down what actually drives purchase decisions across industries, with real examples from brands like Rhode, Sephora, and Apple.

Empowering Women in Marketing: A Leadership Q&A with Lexi Clarke (via ActionRocket)

🔗 https://www.actionrocket.co/blog/empowering-women-in-marketing-a-leadership-q-a-with-lexi-clarke

Why I recommend it: A quick but grounded Q&A on leading with kindness without sacrificing ambition — covering mentorship, emotional intelligence, and why the best leaders bring their whole self to the table instead of fitting a mold.

Mining Customer Reviews for Content Creation using a Custom GPT (via WTS)

🔗 https://www.womenintechseo.com/knowledge/customer-reviews-for-content-creation-gpt/

Why I recommend it:Your customers are already telling you what to write about — you just have to organize it. This walks through a custom GPT that mines customer reviews and turns them into

You Might Also Like:

Think Fast, Talk Smart
Say What Sticks: The Neuroscience of Memorable Communication feat. Carmen Simon
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: People forget 90% of your content within 48 hours — and the 10% they keep is random unless you engineer it. This episode breaks down how to define your “10% message,” prime your audience’s brain to receive it, and use strategic repetition to make sure the right thing sticks.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

DAVID PROTEIN

Format: TikTok
Why I like it: If you missed it, David Protein got some unwanted press last week (see here). This TikTok video was a great response, lol.

DISNEY CRUISE LINES

Format: Instagram Ad
Spotted By: Maria Simone, Homestead
Why I like it: A great emotionally-driven story arc. And almost no words were spoken.

JUSTINA PERRO

Format: OOO Email
Spotted By: Justina P.
Why I like it: A fantastic way to demonstrate to your readers that you can do the thing you say you can.

IKEA

Format: Ad
Why I like it: A great way to leverage curiosity to pull your reader in further.

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

Subscribe now

Every spring, the same copy starts showing up everywhere.

“New season, new you.”
“Fresh starts begin here.”
“Spring into savings.”

You’ve seen it. You’ve probably written some version of it (I know I have). And if you’re being honest, you know it doesn’t really land.

The problem isn’t the writing. It’s the thinking that came before the writing.

Why most seasonal copy falls flat

Most seasonal copy fails for one reason: the writer treated the season like a costume. They dressed the message up in spring colors and called it done. Swap the logo and the message works for anyone, which means it works for no one.

That’s not seasonal copy.
That’s seasonal wallpaper.

The brief says “spring campaign” and the writer reaches for the obvious stuff. Florals. Pastels. “Fresh start” energy. It checks the box. It moves the project forward and yet it produces something completely forgettable.

This happens because too many writers and brands want to get through a seasonal moment rather than actually meet it. The season becomes a deadline, not an opportunity.

Imagery vs. feeling

Spring imagery is visual. It’s the stuff you can see and decorate with. Blooms, brightness, lighter layers.

Spring feeling is emotional. It’s the stuff people are actually experiencing.

Renewal after a long stretch of cold and gray. The specific relief of momentum returning. The quiet permission to start something you’ve been putting off.

The former is decoration while the latter is the actual reason seasonal copy can connect.

When you write from the imagery, you’re describing the season from the outside. But when you write from the feeling, you’re writing from inside the experience the reader is already having.

And that’s the whole game, bud.

3 questions to ask before you write

So how do you actually get there?

You slow down before you write. But not to do research – to observe.

Most writers skip this step. They jump from brief to blank page and start assembling. But seasonal copy that works comes from a writer who stopped and actually thought about what this season means to a real person right now. Not aesthetically. Emotionally. Behaviorally.

Three questions worth sitting with before you write anything seasonal:

1. What are people shedding right now?

Spring follows winter. People are coming out of something. Heaviness. Stagnation. A slower, more closed-off version of themselves.

Your reader isn’t just a consumer in spring. They’re a person who’s been waiting for this. What are they finally putting down?

2. What are they moving toward?

This is different from “what do they want to buy.” It’s about energy and direction. Spring is when people start things. New habits. New projects. New commitments to themselves.

If your product or message can live in that movement, you’re writing with the current, not against it.

3. What does this season give them permission to do or feel?

Seasons are social and inherently carry cultural permission. Spring says: it’s okay to be optimistic again. It’s okay to start over. It’s okay to want more. That permission is a real feeling your reader is walking around with. So, write into it.

These answers are your material. The brief tells you what to say. These questions tell you what it should feel like to read it.

What it looks like in practice

Here’s what the difference looks like on the page. Imagine you’re writing a campaign for a productivity app. Spring launch, standard brief.

The surface-level version:

Spring is here. Time to refresh your routine. Start fresh with [App Name] and make this your most productive season yet.

It’s fine. It’s functional. But it’s also completely forgettable.

The version written from inside the feeling:

You’ve been coasting since January – and you know it. Spring has a way of making that obvious. [App Name] helps you build the day you keep saying you’ll get to.

Same product. Same season. Completely different weight.

The second version works better because it meets the reader where they actually are. It doesn’t describe spring. It leverages what spring does to people.

The principle that travels

Spring is the example.
The habit is what travels.

Every seasonal moment carries its own emotional truth. Summer is abundance and escape. Fall is transition and reflection. Winter is stillness and the particular weight of a year ending.

Writers who stop to observe before they write stop producing copy that could belong to anyone. Their work has a specific gravity because it’s written from a specific place.

The brief tells you the season.
Your job is to figure out what the season means.

That’s the work that happens before you write a single word.

Subscribe now

Seasonal copy falls flat when writers skip the fundamentals.

The Copy Principles Swipe File is a reference guide built around the principles that make copy work regardless of the season, the campaign, or the brief.

Not tactics. Not templates. The underlying thinking that drives copy that actually connects.

If you want copy that has real weight to it, start here.

Download for Free

The Copywriter Column is a weekly glimpse into the mind of an agency copywriter. Thinking about subscribing? Here’s what else you can expect.