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

2 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.

🔓 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: 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

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

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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

Subscribe now

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

Subscribe now

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

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

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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.

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.

Subscribe now

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.

Subscribe now

Welcome to the 118th 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 much more!

In this week’s issue:

• Copy Tip: Stop apologizing for the em dash…

• AI Tip: Save your best AI outputs

• Writing is Thinking, But What Happens When You Let AI Do It for You? (via Psychology Meets Writing)

• Communicating Your Brand Values (via Really Good Emails)

• Your Prompts are Fine: Context Engineering is Your Next AI Problem (via Animalz)

• You Can Scale a System. You Can’t Scale Chaos. (via The Copy Minimalist)

• Podcast Pick: Show Me the Money Words with Copywriting Expert, Joanna Wiebe

• Swipe File Additions

• Job Opps

Copy Tip of the Week

Stop apologizing for the em dash…

There’s a growing instinct to flag the em dash as “AI-sounding.”

ChatGPT leans on it hard, so now every time one shows up, someone’s internal alarm fires.

The problem: the em dash has been a staple of good writing for decades.

Removing it because of association isn’t editing.

It’s pattern-matching disguised as judgment.

All punctuation controls two things: pacing and hierarchy.

The em dash does both at once.

A comma is a breath. A semicolon is a pivot. A period is a stop. An em dash is a spotlight.

It says: this part matters.

Copy is about directing attention. The em dash is one of the few punctuation marks built for that job.

Read how to use it here →

AI Insight of the Week

Save Your Best AI Outputs

Most teams generate great AI outputs…
and then lose them forever.

That’s a mistake.

The best outputs are training data for your future prompts.

When AI produces something great, save it and label it:

• What the task was

• Why the output worked

• What prompt produced it

After a few weeks, you’ll have a library of proven patterns.

The fastest way to improve AI output is simple: show it what good looks like.

Must-Read Articles

Writing is Thinking, But What Happens When You Let AI Do It for You? (via Psychology Meets Writing)

🔗

Psychology Meets Writing

Writing is thinking, but what happens when AI does it for you?

​​”Nowadays, the hand-made article hasn’t a hope. It can’t possibly compete with mass-production. Carpets…chairs…shoes…bricks…crockery…anything you like to mention— they’re all made by machinery now. The quality may be inferior, but that doesn’t matter. It’s the cost of production that counts. And stories—well—they’re just another product, like carpets …

Read more

2 months ago · 87 likes · 31 comments · Psychology Meets Writing

Why I recommend it: An MIT study found that people who wrote essays with ChatGPT showed the weakest brain connectivity of all three test groups—and 83% couldn’t even quote from what they’d “written.” If writing is how we think, outsourcing it isn’t saving time—it’s losing your creative soul.

Communicating Your Brand Values (via Really Good Emails)

🔗 https://reallygoodemails.com/school/communicating-brand-values-human-connection-marketing

Why I recommend it: If your last 6 months of emails are all promos and product pushes, your subscribers know what you sell — but not who you are. This talk (it’s a little long) breaks down how brands like IKEA, Boots, and Decathlon turn values into trust (and what happens when brands fake it).

Your Prompts are Fine: Context Engineering is Your Next AI Problem (via Animalz)

🔗 https://www.animalz.co/blog/context-engineering

Why I recommend it: Your AI outputs are probably mediocre not because your prompts are bad, but because the model doesn’t know enough about your brand, audience, or point of view. This breaks down “context engineering” — the system design work that separates generic AI content from content worth publishing.

You Might Also Like:

Talking Too Loud with Chris Savage
Show Me the Money Words with Copywriting Expert, Joanna Wiebe
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Joanna Wiebe — the person who coined “conversion copywriting” — joins Wistia’s Chris Savage to break down why most marketers write copy backwards (art first, strategy never) and what the order of operations should actually be. If you’ve ever wondered why your headline isn’t landing or your emails feel flat, this 54-minute conversation will reframe how you think about every word you publish.

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

Pretty Fly Copy

PATH PROJECTS

Format: Email
Why I like it: Great comparison email between two similar products. For a customer torn between these two items, it’s a great send. They should use this for a browse abandonment flow.

APPLE

Format: Email
Why I like it: The headline. Get it?

841 MEMORIAL

Format: Street Sign
Why I like it: One day this last week as I was sitting in traffic that was inching slowly forward every few minutes, I looked over and saw this sign in front of an apartment complex. Effective.

Career Opportunities

These remote opportunities are updated every week with copywriting and marketing roles ambitious job-seekers should definitely apply for. 

Copywriter & Content Strategist at Homestead Studio
📍Remote (Mexico!!) **ℹ️ Agency 💸 Location Dependent

Temporary Sr. Copywriter at ISPY
📍Remote ℹ️ B2C 💸 $50 - $60/hr (USD)

Senior Content Strategist at Rasa
📍Remote ℹ️ B2B 💸 $130,000 - $150,000/yr (USD)

DTC Email Copywriter at Stimulate
📍Remote ℹ️ DTC Agency 💸 $35 - $50/hr (USD)

Creative Copy Lead at Native Pet
📍Remote ℹ️ B2C 💸 Not Listed

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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Something strange happens when an agency starts growing.

More clients come in.
More people get hired.
More work ships.

And somehow, everything gets harder.

Not harder in the way that meaningful work is hard. Harder in the way that signals something is wrong.

More miscommunication. More rework. More meetings that exist just to get everyone on the same page, because nobody was on the same page to begin with.

The instinct when this happens is to fix operations. Tighten up the project management. Build out better SOPs. Hire someone to wrangle the chaos.

Those are reasonable moves. But they rarely hold.

Not because the systems are bad, but because there’s nothing solid underneath them.

What You’re Actually Scaling

Here’s the question most agencies skip: what are we scaling?

When things start to grow, the assumption is that growth itself is the goal.

Get bigger.
Take on more.
Hire faster.

But growth without direction just produces more of what you already have. If what you already have is unclear, disorganized, and reactive, that’s exactly what gets amplified.

You can scale a system. You can build a repeatable process and grow it. You can add people to a machine that already works and watch it produce more, reliably.

But you can’t scale confusion.

You can’t systematize something that was never clear to begin with. When the foundation is shaky, every new layer of growth makes the whole thing wobble more.

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The Foundation Nobody Wants to Slow Down For

The foundation isn’t your tech stack. It isn’t your project management tool or your onboarding checklist or your Slack channel structure.

Those are all useful. But they’re all really just second-order decisions.

The real foundation is identity and positioning.

Who is this agency?
Who does it serve?
Why does it matter to those people specifically?

These sound like branding questions. They’re not. They’re operational ones.

When you know who you are and who you serve, you know what to say yes to. You know how to scope work, how to structure your team, and how to deliver consistently.

Your systems have a reason to exist, and your people have a direction to follow.

When those answers are unclear (and in most agencies, let’s be honest, they’re at least a little gray), every downstream decision becomes a judgment call. Not a principled one. A guess.

And when the whole team is guessing, you get a lot of good people pulling in slightly different directions.

That’s not dysfunction.
That’s what happens when the foundation is assumed instead of defined.

Skill Isn’t the Missing Piece

Most agencies I’ve seen aren’t short on talent. They have capable strategists, sharp writers, and strong designers.

The work itself isn’t the problem.
The context the work happens inside is the problem.

Skilled people do their best work when the direction is clear and the systems around them make sense.

Take those same people and drop them into an agency where the positioning is vague, the processes keep shifting, and every project feels like it’s being figured out from scratch, and the quality drops.

Not because the people got worse.
Because the environment did.

Skill and craft matter. You absolutely need baseline ability across every department to build anything worth scaling. But that ability already exists in most shops.

The gap isn’t in what your people can do – it’s in whether the structure they’re operating inside gives them a chance to do it well.

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Getting the Order Right

This isn’t a framework. It’s an observation about what I keep seeing work and what I’ve lived on both sides of.

I’ve been part of organizations that tried to scale on ambition alone. Good people, good intentions, no clear identity underneath.

Every new client felt like a reinvention. Every process lasted until the next fire drill. Growth made things louder, not clearer.

Working with Homestead Studio has been a different experience.

I came on in the earlier days and got to be part of shaping that identity as it took form. Who they are, who they serve, and why it matters to those people.

I watched that clarity get honed, and I helped build on it within my own department.

The difference is obvious.

Systems hold because they’re built on something defined. People do strong work because the direction supports them, not because they’re constantly compensating for what’s missing.

That contrast sharpened something for me.

The agencies that scale well tend to get the order right. They start with clarity about who they are and who they’re for. Not a one-time exercise, but an ongoing commitment to staying honest about that answer as things change.

They build systems and processes on top of that clarity. Not borrowed templates from some other agency’s playbook, but structures that reflect how they work, for the clients they serve, with the team they’ve built.

And they sharpen craft within that structure. They give people room to grow and get better inside a system that actually supports the kind of work they’re trying to produce.

Scale, when it happens, feels like extension.
More of what already works.
Not an explosion of activity that nobody can keep up with.

The Honest Version

If growth is getting louder but not clearer, the problem probably isn’t your systems. It’s that your systems don’t have anything solid to stand on.

Before you add more people, more tools, more process, ask the uncomfortable question: do we actually know who we are and who we’re building this for?

If the answer is crisp, your systems will hold weight.
If it isn’t, no amount of operational polish will fix the wobble.

Start there.
The rest follows.

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If your agency is growing but the systems aren’t keeping up, let’s talk.

On the side, I work with department leads to diagnose where their copy operation is breaking down and share the systems that can fix it. QA processes, onboarding frameworks, brand voice documentation, revision scope management, AI workflow integration, etc.

If you’re a team lead who feels like you’re the bottleneck, this is built for you.

→ Book a Call

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

Subscribe now

Welcome to the 117th 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 much more!

In this week’s issue:

• Copy Tip: Stop Writing for the Click.

• AI Tip: Optimize for “Editor Time,” Not “Generation Time”

• Claude Cowork for Marketers (via Customer.io)

• How to Write Alt Text Correctly With Context (via Action Rocket)

• 5 Creative Tensions That Become Idea Engines (via Copywriter Collective)

• Why Your Content Strategy Feels Harder Than It Should (via The Copy Minimalist)

• Podcast Pick: How to Build a Magnetic Brand that Sells Itself ft. Seth Godin

• Swipe File Additions

• Job Opps

Copy Tip of the Week

Stop Writing for the Click.

Most copy is obsessed with the next micro-yes.

Open the email.

Click the link.

Add to cart.

It is very important! Don’t get me wrong. You should absolutely sell the click, but you shouldn’t stop there.

When you do, that mindset creates shallow persuasion and chases action without building belief.

Instead, write for commitment.

Before you ask for the action, ask yourself:

• What does my reader need to believe to take this step?

• What fear or friction is still sitting under the surface?

• What would make this feel like a smart decision, not an impulsive one?

If you sell a $200 supplement, they need to believe it will work for someone like them.

If you sell a $2,000 program, they need to believe they are capable of following through.

If you sell anything subscription-based, they need to believe this will fit into their life long term.

Clicks come from curiosity.

Commitment comes from clarity and confidence.

And creating clarity is your job.

When you sit down to write this week, don’t start with the headline. Start with the belief shift. Identify the one idea that must change in their mind. Then build everything around that.

AI Insight of the Week

Don’t Automate the Whole Workflow. Automate the Friction.

Don’t try to build end-to-end AI systems.

That’s usually overkill.

Instead, look for the 20% of the process that:

• Slows everyone down

• Requires formatting or synthesis

• Feels mentally repetitive

That’s your automation target.

Examples:

• Turning research into a brief

• Pulling insights from reviews

• Converting strategy notes into copy angles

• Writing first-pass variations

Don’t replace the strategist. Remove the friction before or after their thinking.

AI is strongest in the seams — between research and strategy, between strategy and execution, between execution and reporting.

Automate the friction, not the craft.

Must-Read Articles

Claude Cowork for Marketers (via Customer.io)

🔗 https://customer.io/learn/lifecycle-marketing/claude-cowork-for-marketers

Why I recommend it: If you’re still spending hours building reports and campaign briefs instead of thinking about strategy, this article reframes what AI should actually be doing for you — not advising, but executing.

How to Write Alt Text Correctly With Context (via Action Rocket)

🔗 https://www.actionrocket.co/blog/how-to-write-alt-text-correctly-with-context

Why I recommend it: Alt text isn’t just a technical checkbox — it’s a copywriting decision, and this piece shows why the same image needs completely different descriptions depending on the email it lives in. Worth a read if you want a fast, practical win on accessibility that also sharpens how you think about context-driven writing.

5 Creative Tensions That Become Idea Engines (via Copywriter Collective)

🔗 https://copywritercollective.com/creative-tension-copywriting-engines/

Why I recommend it: Good reframe for anyone who treats constraints as obstacles: the article argues that deadlines, budget limits, and conflicting feedback aren’t enemies of good copy — they’re the pressure that strips away the decorative and forces you to find the thing that actually works.

You Might Also Like:

THE 505 PODCAST
How to Build a Magnetic Brand that Sells Itself ft. Seth Godin
🎧 Watch on YouTube

Why I recommend it: Godin works backward from why tactics work instead of just listing them. Three ideas earn the hour: “remarkable” reframed as literally worth remarking about — not a tactic but a design constraint. The smallest viable audience — ten people who trust you will always outperform ten thousand who scroll past you, because the math of trust beats the math of reach. And consistency over authenticity — “authentic” has become a permission slip to be undisciplined, while consistency is what actually builds a brand promise over time.

If you’d rather understand the physics of marketing than memorize the playbook, this one’s for you.

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

Pretty Fly Copy

ETC

Format: Ad Dump
Spotted By: Kelly Moran
Why I like it: Honestly, just a great collection of spring-flavored inspo worth bookmarking.

POWER MY 401K

Format: Ad
Spotted By: Derek Hambrick
Why I like it: Such a great play on words.

BASS PRO SHOPS

Format: Email
Why I like it: Love the subject line. It was written for guys like me. Not to mention the name of the sale in the hero. Brilliant.

Career Opportunities

These remote opportunities are updated every week with copywriting and marketing roles ambitious job-seekers should definitely apply for. 

Copywriter & Content Strategist at Homestead Studio
📍Remote (Mexico!!) ℹ️ Agency 💸 Location Dependent

Senior Copywriter at Arctic Wolf
📍Remote ℹ️ B2B; Cybersecurity 💸 Not listed

Writer, Content Marketing at Stripe
📍Remote ℹ️ Fintech 💸 $145,000 - $217,000/yr (USD)

Senior Copywriter at Paula’s Choice Skincare
📍Remote ℹ️ B2C Beauty 💸 $100,000 - $110,000/yr (USD)

Senior Copywriter at Molekule
📍Remote ℹ️ B2C 💸 Not Listed

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, you tell yourself you’re going to clean up your content strategy.

You open the spreadsheet. You tag a few old posts. And then, about two hours in, the energy dies. The audit becomes a catalog. The catalog becomes a project. The project gets deprioritized. Nothing gets cut.

Sound familiar?

The problem isn’t the audit. It’s the mindset behind it. An audit catalogs. It tells you what you have. What most content strategies actually need isn’t an audit at all. It’s an edit.

An edit makes judgments. It asks what belongs and what doesn’t. It requires a standard, not just a spreadsheet.

Before you can cut well, you need to know what you’re cutting toward.

How Strategies Accumulate Instead of Evolve

Nobody plans to build a bloated content library. It happens gradually, one reasonable decision at a time.

A new product launches, so you add a topic cluster. A trend gets hot, so you cover it. A team member has a good idea, so you publish it.

Each addition makes sense in the moment. The problem is that nothing ever gets removed.

New topics get added. Old ones don’t get retired. Publishing cadence gets mistaken for strategic momentum. “I’ve always covered this” becomes a rationale by default.

Over time, your content library stops reflecting where you’re going. It starts reflecting where you’ve been.

The strategy that made sense two years ago is still running, quietly, in the background, pulling in the wrong readers, signaling the wrong things, confusing the audience you’re actually trying to reach.

A content strategy that never gets pruned eventually becomes a history of old assumptions.

That’s not a library.
That’s an archive.

Set the Standard Before You Pick Up the Scissors

Here’s where most pruning efforts go wrong. A lot of folks skip straight to the cutting and either remove too little because they’re afraid, or too much because they’re frustrated.

Both outcomes come from the same root cause: no clear standard for what earns a place in the strategy.

Before you touch a single piece of content, get honest answers to these questions:

What is this piece supposed to do? Attract new readers? Educate existing ones? Support a conversion? Retain a customer? If you can’t answer that, the piece doesn’t have a job.

Who is it actually for? Not in theory. Right now, given your current audience and positioning, is this for the person you’re trying to reach?

Is it still true? Markets shift. Your thinking evolves. A piece that was accurate two years ago might be actively misleading today.

Does it reflect how you think now, or how you used to think? This one is quieter, but it matters. Your content is a public record of your perspective. Old thinking left up without context is a credibility problem waiting to happen.

Here’s a simple test: if a piece of content fell off your site tomorrow and nobody noticed, what does that tell you?

You don’t need a complex scoring rubric. You really just need honest answers to simple questions.

Where AI Actually Helps

This is one of those processes where AI earns its keep, not as a decision-maker, but as a pattern-spotter.

The tedious parts of a content review — cross-referencing topics, flagging redundancies, summarizing what you’ve already said and how often — are exactly the kind of work AI handles well.

Feed it your content library and ask it to surface themes you’ve covered repeatedly.

Ask it to identify topic clusters where you have four pieces saying roughly the same thing.

Ask it to compare older content against your current positioning language and flag where the gap is widest.

What AI can’t tell you is whether a piece still matters to your audience, or whether a weak performer is underperforming because the topic is exhausted or because the execution was just bad.

That distinction changes the call entirely. A bad piece on a strong topic deserves a rewrite. A solid piece on a dead topic deserves retirement.

AI speeds up the inventory, but you should still have to make the call.

How to Cut Without Panicking

Most people hesitate to cut content for a reason that sounds strategic but isn’t: sunk cost.

“We put a lot of work into this.”
“It might pick up traffic later.”
“I don’t want to lose what we built.”

These feel like caution. They’re actually attachment. And attachment to old content is one of the quietest ways a strategy stays stuck.

The move is to replace that instinct with a clearer one. Every piece of content you review deserves one of three calls.

1. Retire it. The content no longer reflects your positioning, your audience, or what you know to be true. It’s not just underperforming. It’s misaligned. Keeping it doesn’t preserve value. It creates confusion.

The governing question: does this still represent how you think?

2. Update it. The core idea is sound, but the execution is dated, incomplete, or underdeveloped relative to where your thinking is now. This is the most common call, and the most underused. You’re likely quicker to publish new content than to strengthen what already exists.

The governing question: is the foundation worth keeping, even if the structure needs work?

3. Consolidate it. You’ve covered this topic in three different places, and none of them do it definitively. Pick the strongest version, build it out, and let the others go. Your audience doesn’t need four takes on the same subject. They need one clear one.

The governing question: are you adding clarity or just adding volume?

Across all three calls, there’s one governing question that cuts through the noise: is this content still doing a job? Not “is it good?” Not “did it used to work?” Is it earning its place right now?

The content you keep is a statement about what you currently believe. Treat it like one.

The Edit Is the System

This isn’t about getting lean for spring. It’s about building a habit of editorial judgment.

The brands and strategists with the clearest content aren’t necessarily publishing less. They’re publishing with more intention. And they’ve stopped letting the library grow by default and started asking, regularly, whether what’s there is still doing what it’s supposed to do.

The annual audit isn’t the system.
The question “does this still belong?” is the system.

Spring is just a reminder.
The edit should be ongoing.

Want to dive deeper into the principles that make copy actually work for your team?

I’ve distilled 20+ years of marketing expertise into a free micro-course called The Minimalist Copywriter’s Playbook. It covers the 5 core principles I use every time I sit down to write – ones you can apply immediately.

Grab it here →

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

Welcome to the 116th 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 much more!

(Well, this week is an outlier. Unforeseen circumstances reduced my ability to source in a timely manner this week – back to regular programming next week!)

In this week’s issue:

• Copy Tip: You Can’t Out-Write a Weak POV

• Article Recommendations:

  • What Are AI Agents in Marketing & How Are They Actually Being Used Today? (via Iterable)

  • The Ambiguity Effect: Why Unclear Marketing Kills Decisions (via Kath Pay

  • The Future of Brand Creativity Belongs to the Small and Reckless (via Branding Strategy Insider)

  • Inclusive Marketing Beyond Buzzwords (Black History Month Edition)

• Podcast Pick: Tested Advertising Methods: The Blueprint for Higher Conversions

Copy Tip of the Week

You can’t out-write a weak point of view.

Most copywriters think clarity is about better word choice.

It’s not.

Clarity comes from conviction.

If you don’t know where you stand on what you’re selling, no amount of editing will save you.

Your copy will wander. Your tone will hedge. Your reader will sense the hesitation.

Strategy shows up in tone, not just structure.

A strong point of view doesn’t need clever frameworks to land. It needs commitment to an idea worth defending.

Weak copy says: “This product might help some people in certain situations.”

Strong copy says: “If you’re tired of X, this solves it.”

The difference is perspective, not perfection.

Before you write another word, ask yourself:

• What do I actually believe about this product?

• What problem does it solve that others ignore?

• Who is this for — and who is it not for?

Answer those first.

Then write.

Must-Read Articles

What Are AI Agents in Marketing & How Are They Actually Being Used Today? (via Iterable)

🔗 https://iterable.com/blog/ai-agents-in-marketing/

Why I recommend it: Breaks down the difference between AI agents, automation, and generative AI — and why the distinction matters. The core idea: automation follows rules you set, but agents adapt toward goals you set, handling the thousands of micro-decisions (timing, channel, targeting) that no human team can optimize manually efficiently. Worth reading if you want a clearer mental model for where AI actually fits into your workflow versus where it’s just a buzzword.

The Ambiguity Effect: Why Unclear Marketing Kills Decisions (via Kath Pay

🔗 https://www.linkedin.com/pulse/ambiguity-effect-why-unclear-marketing-kills-decisions-kath-pay-odwie/

Why I recommend it: Explains the cognitive bias that’s probably killing your click-through rates — and it’s not what you think. The Ambiguity Effect shows that when people can’t instantly tell what happens after they click, they don’t click. It’s a good gut-check on whether your “clever” copy is actually creating uncertainty instead of interest.

The Future of Brand Creativity Belongs to the Small and Reckless (via Branding Strategy Insider)

🔗 https://brandingstrategyinsider.com/the-future-of-brand-creativity-belongs-to-the-small-and-reckless/

Why I recommend it: A spicy argument that big agencies are using AI to accelerate sameness, not creativity — and that the real advantage is shifting to small, opinionated teams. The core tension: AI eliminates the scale advantage that holding companies used to monopolize, which means taste, judgment, and creative risk become the new moat. Whether you work in-house or agency-side, this reframes how you should be thinking about AI’s role in your own work.

You Might Also Like:

The Russel Brunson Show
Tested Advertising Methods: The Blueprint for Higher Conversions
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Russell Brunson walks through the basics of A/B testing using John Caples’ Tested Advertising Methods as the backbone — and the takeaway is dead simple: specificity crushes generality in headlines. A good refresher on why the fundamentals from old-school direct response still run the game!

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 few months, the same thing happens. Brands dig through their stock photo libraries, post something about Black History Month (or the other holidays), and hope it lands.

Most of it doesn’t.

And if you’ve worked in marketing for more than a couple of years, you can feel the difference between a brand that means it and a brand that’s checking a box.

But here’s what I want you to sit with: the problem isn’t the post. The problem is that inclusion only shows up when the calendar says it should.

If your marketing efforts only reflect the people you serve during designated months, it doesn’t reflect them at all. It performs for them. And your audience can tell the difference.

This isn’t an article about what to post for Black History Month – after all, I am the very working definition of a bearded white guy.

But it is about building the kind of marketing practice where the question “would our audience feel represented by this?” gets asked on any given Tuesday.

The real problem with performative inclusion

You’ve seen it. The heritage month graphic that doesn’t connect to anything the brand actually does. The stock photo swap where the creative stays exactly the same but the faces change. The Slack thread two days before the month starts: “Should we say something?”

If you’re asking whether you should say something, you’ve already answered the question. You don’t have anything to say. You have something to react to.

The root cause is simple.

Most teams treat inclusion as a content topic instead of a creative standard. It gets assigned like a campaign brief. Someone writes it, someone approves it, it goes out, and everyone moves on until the next awareness month rolls around.

If you’re a copywriter, you’ve probably been on the receiving end of this. “Can you make this feel more… diverse?” is not a creative direction. It’s a symptom of a team that hasn’t thought about inclusion until the deadline forced them to.

If you lead a creative team, ask yourself an honest question. Does inclusion come up in your process only during heritage months or after a PR misstep? If so, it’s not a principle. It’s damage control.

Principles show up every day.
Campaigns have end dates.

What inclusive marketing actually looks like as a principle

So what does it look like when inclusion is built into the work instead of bolted on? It operates on three levels. And most teams only think about the first one.

1. Language

This is where most people start, and it matters. The words you choose carry assumptions.

• Who is your “default” customer?

• When you write “professional,” whose version of professional are you picturing?

• When you say “family,” what does that family look like?

Every piece of copy reflects someone’s experience as the norm. The question is whether you’ve examined whose experience that is.

2. Representation

This goes beyond visuals, though visuals are part of it.

Who shows up in your testimonials? Your case studies? Your email campaigns? Not as a diversity checkbox, but as a genuine reflection of the people you serve.

If your customer base is broad but your marketing only features one slice of it, that’s not a creative choice. That’s a blind spot.

3. Process

This is the one most teams skip, and honestly, it’s probably the most important.

Who is in the room when creative decisions get made? Whose perspective is missing from your brief, your review, your approval chain?

You can fix language with a style guide. You can fix representation with better casting. But if the people making the decisions all share the same blind spots, the work will keep reflecting those blind spots no matter how many stock photos you swap.

The principle underneath all three: inclusive marketing isn’t about adding diversity to your messaging. It’s about removing the assumptions that made your messaging narrow in the first place.

And if you need the business case to bring this to a stakeholder, the data is clear.

A 2024 study from Unilever and Oxford’s Saïd Business School found that inclusive advertising delivers 16% higher long-term sales and makes brands 62% more likely to be a consumer’s first choice.

Microsoft’s research showed that inclusive ads drove a 23-point lift in purchase intent across all audiences. Not just among represented groups. ALL audiences. The highest lift was actually among viewers who weren’t personally represented in the creative.

That last point matters. Inclusive marketing doesn’t shrink your audience. It grows it.

How AI can help (and where it can’t)

AI tools have gotten genuinely useful for catching biased or exclusionary language. They’re worth building into your review process, with one important caveat: they’re a first pass, not a final answer.

Here’s where they add value.

At scale, human reviewers miss patterns. We get used to our own defaults. But AI catches the things we’ve stopped noticing.

A gendered assumption in a headline. An ableist phrase that’s become industry shorthand. Terminology that’s shifted since the last time you checked the style guide.

Several tools are built for this.

Enterprise platforms like Writer let teams set customizable inclusive language rules tied to their brand guidelines. Salesforce used Acrolinx to audit and replace non-inclusive technical language across their entire product documentation.

And for individual writers and smaller teams, Grammarly Premium flags sensitivity and inclusivity issues, Microsoft Editor checks for bias across gender, age, race, and sexuality, and the free open-source linter Alex.js catches insensitive patterns across 218+ categories.

But here’s the limitation you need to understand: almost all of these tools analyze text only. They don’t evaluate your visuals. They don’t assess cultural context. They can’t tell you whether your tone feels authentic or performative to the community you’re trying to reach.

So, obviously, AI is only one layer of a review process. It catches the obvious patterns. But a human reviewer with cultural competency catches the rest. The strongest workflow pairs both. Let the tool do the first scan. Then put human eyes on the work, ideally eyes that bring a different perspective than the person who wrote it.

The principle here is the same one that applies to every AI workflow: the tool accelerates your judgment. It doesn’t replace it.

The simplest place to start

If you’re a copywriter, try this before your next project ships – read your copy one more time and ask a single question: “Who might not see themselves in this?”

Not as a guilt exercise. As a craft exercise. It takes two minutes. And once you start doing it, you’ll be surprised how often the answer changes something.

If you lead a creative team, add one line to your brief template: “Who is this speaking to, and who might it be excluding?”

That question, asked early, changes the entire conversation before the work starts. It’s easier to build inclusion into a brief than to retrofit it into a finished campaign.

Inclusive marketing isn’t about getting it perfect. Nobody gets it perfect (especially me). It’s about building the habit of asking better questions, consistently, across every project.

And that’s what separates a principle from a performance.

Resources: Writing more inclusive messaging

If you want to go deeper, these are worth your time.

Style Guides and Language Resources

Conscious Style Guide — A methodology for making inclusive language decisions, not just a word list. Updated continuously. AP Stylebook editors have called it the best tool book available.

Diversity Style Guide — Searchable database of 700+ terms drawn from 23 source guides including NABJ, NCDJ, and GLAAD. Best for quick terminology lookups.

GLAAD Media Reference Guide — The standard reference for writing about LGBTQ+ people accurately. Used by AP, Reuters, and the New York Times.

Frameworks

Unstereotype Alliance 3Ps Framework (Presence, Perspective, Personality) — A practical three-question test for evaluating representation in any creative asset. Backed by UN Women.

Books

Inclusive Marketing by Jerry Daykin (Kogan Page, 2022) — A practical book available for marketing teams. Checklists and frameworks for every stage of creative development, with case studies from Guinness, Microsoft, Unilever, and Mattel.

AI Tools

Alex.js — Free, open-source language linter that catches insensitive writing across 218+ patterns. Good starting point for individual writers.

Want to dive deeper into the principles that make copy actually work for your team?

I’ve distilled 20+ years of marketing expertise into a free micro-course called The Minimalist Copywriter’s Playbook. It covers the 5 core principles I use every time I sit down to write – ones you can apply immediately.

Grab it here →

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

Subscribe now

Welcome to the 115th 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 much more!

In this week’s issue:

• Copy Tip: Constraints force decisions.

• AI Tip: Optimize for “Editor Time,” Not “Generation Time”

• Claude (via How to AI)

• The Mimicry Effect (via Stacked Marketer)

• Personal vs. Personalized: What Real Connection Looks Like in the Inbox (via Customer.io)

• Podcast Pick: Why Cognitive Load is Holding Back Your Business

• Swipe File Additions

• Job Opps

Copy Tip of the Week

Most copywriters think more options = better work.

The opposite is true.

Constraints force decisions.

Decisions produce clarity.

And clarity is what makes copy resonate.

Think about it.

When a client says “write whatever you want,” you freeze. When they say “500 words, one CTA, speak to frustrated founders,” you get to work.

This is why the best copywriters don’t fight constraints.

They request them.

Before you write anything, ask:

Who is this for?
What do they already believe?
What’s the one action I want them to take?
What can I not say?

Four questions, and suddenly the page isn’t blank anymore.

Confidence doesn’t come from having more choices.

It comes from eliminating most of them before you start.

AI Insight of the Week

Optimize for “Editor Time,” Not “Generation Time”

Everyone loves saying, “AI writes this in 30 seconds.”

But speed of generation isn’t the real metric.

The real question is: How fast can we confidently approve this?

In an agency environment, output isn’t done when it’s generated—it’s done when it’s shipped. If editors are still rewriting tone, fixing structure, softening claims, adjusting voice, or reframing angles, then AI isn’t actually saving you time. It’s just shifting where the work happens.

⸻

Start tracking where editors consistently intervene.

Is tone drifting too aggressive? Are structures too formulaic? Are compliance edits happening late? Is voice slightly “off” every time?

Those patterns are signals—not about the quality of your editors, but about gaps in your context.

Instead of fixing the copy again and again, patch your prompts. Add clear voice guardrails. Include approved structural frameworks. Set explicit claim boundaries. Drop in “never say this” examples.

You don’t improve speed by pushing writers to edit faster. You improve speed by making first drafts more approvable.

⸻

Every minute you eliminate in revision compounds across campaigns, brands, clients, and writers.

Generation speed is a vanity metric.

Approval speed is the operational one.

Must-Read Articles

Claude (via How to AI)

How to AI

Claude.

Read more

3 months ago · 411 likes · 104 comments · Ruben Hassid

Why I recommend it:
Breaks down how the new Claude Cowork workflow lets the model read your files directly and act more like an assistant than a chat box, helping you generate context-rich, brand-consistent outputs without wrestling with prompts. It’s worth your time because it reframes how AI can augment creative work — not just draft language, but actually internalize your style and context to save time and keep messaging on point.

The Mimicry Effect (via Stacked Marketer)

🔗 https://cm.stackedmarketer.com/t/j-e-ydtilrky-hrudttiyiy-yd/
Why I recommend it:
This newsletter snippet (middle section) explains how mimicry — showing traits or language that mirror your audience — builds affinity and trust, making your marketing feel more relatable and persuasive. For a marketer or copywriter, it’s a quick psychology hack you can apply to audience research, tone, and creative choices to deepen connection and persuasion.

Personal vs. Personalized: What Real Connection Looks Like in the Inbox (via Customer.io)

🔗 https://customer.io/learn/personalization/personal-vs-personalized-email
Why I recommend it:
This piece draws a clear line between simple customization like inserting names and true personalization driven by behavior, timing, and context. It’s a practical read for email-focused marketers because it pushes you beyond surface tricks toward crafting campaigns that feel genuinely helpful — which improves engagement and outcomes.

You Might Also Like:

The StoryBrand Podcast
Why Cognitive Load is Holding Back Your Business
🎧 Listen on iTunes | Listen on Spotify | Watch on YouTube

Why I recommend it:
While I don’t necessarily align with ALL of Donald Miller’s commentary here (he gets a little political), the message still resonates: you need to reduce the cognitive load your message has on your immediate audience. He walks through a few examples in real time, which is helpful in understanding the main point.

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

Pretty Fly Copy

Salt Shack

Format: Poster
Spotted By: Jade & Lee Trott
Why I like it: Most signs explaining rules inside of businesses exist for a reason: someone’s done that thing before. This is one of those situations you WANT to know the story behind the sign, and they deliver.

Cushionaire

Format: Email
Why I like it: Remarkably simple (and clean) email. I also enjoyed how the “Shine Bright” headline and the “meets a little sparkle” subheadline work together. 10/10.

Jupiter

Format: Email
Spotted By: Email Love
Why I like it: I mean, when live gives you lemons, make lemonade someone steals your merch off a truck, make a marketing campaign. But seriously, I love the strategy here.

Career Opportunities

These remote opportunities are updated every week with copywriting and marketing roles ambitious job-seekers should definitely apply for. 

Creative Specialist, Copywriter at LEGO
📍NOT REMOTE (Boston, MA) **ℹ️ B2C 💸 $107,000 - $161,000/yr (USD)

Digital Copywriter at Stibo Systems
📍Remote ℹ️ B2B 💸 Not listed

Copywriter & Content Strategist at Homestead Studio
📍Remote (Argentina, Mexico, Philippines) ℹ️ Agency 💸 Location Dependent

Senior Copywriter at Golden Hippo
📍Remote ℹ️ B2C Wellness 💸 $91,000 - $121,000/yr (USD)

Senior Copywriter (Email) at TakeProfitTrader
📍Remote ℹ️ B2B/Finance 💸 $100,000 - $120,000/yr (USD)

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

✌️
Matt

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February is when the truth starts showing.

The New Year energy has worn off. The big goals are still on the board, but the daily grind is back.

And somewhere in that grind, your team is bumping into the same friction they bumped into last year. The same handoff confusion… the same unclear briefs… the same status updates that take longer to write than the work they’re describing.

Nobody’s complaining, though. And that’s the thing.

When a process is painful long enough, people stop mentioning it. They just work around it. They build little workarounds and coping mechanisms and unspoken agreements.

The silence isn’t approval though.

So if you’re leading a creative team and you want to avoid the February slump, here’s my suggestion: skip the motivational Slack message and fix a workflow instead.

Start by Noticing What You’ve Stopped Noticing

You don’t need a full audit. You just need a few honest questions.

Where do things slow down every single time? Not occasionally. Every time. There’s something there.

What do people ask clarifying questions about repeatedly? If the same confusion keeps surfacing, the process is the problem, not the people.

Where do you see the same mistakes happening? Repeated errors usually point to missing information or unclear expectations upstream.

You’re not looking for everything that’s broken. You’re looking for one or two friction points that would make a real difference if they got fixed.

3 Workflows Worth Fixing First

Most creative teams share the same pain points. These are the ones I’d look at first.

1. Handoffs

The moment work moves from one person to another is where context goes to die.

Client hands off to project manager. Project manager hands off to copywriter. Copywriter hands off to strategist, or designer, or both. And somewhere along that chain, key details vanish. The original intent gets diluted. Someone ends up working from assumptions instead of information.

Most handoff problems aren’t about tools. They’re about expectations.

The fix is simple, if not easy: define what “done” looks like before the handoff happens. Not after.

What should be included? What questions should already be answered? If a brief is coming from a client, what does the PM need to clarify before it reaches the writer? If copy is going to design, what context does the designer need to execute without guessing?

Make it explicit. Write it down. Refer back to it.

2. Status updates and check-ins

If your team spends more time reporting on work than doing it, something has drifted.

I’ve heard horror stories of teams buried in daily standups, weekly syncs, and project trackers that require manual updates across multiple platforms. That’s not communication. That’s overhead!

The fix is to reduce frequency and increase clarity. One update with real information beats five pings.

And if you’re manually aggregating status from multiple sources, consider letting AI do that part. Pull project updates from where the work actually lives. Don’t ask your team to summarize what’s already written somewhere else.

3. Documentation and briefs

Bad briefs create bad work. Incomplete briefs create rework. And both waste time your team doesn’t have.

The fix isn’t more fields. It’s the right fields. Standardize the inputs you actually need and kill the ones nobody fills out anyway.

If you want to layer in AI here, use it to draft first-pass documentation or flag incomplete briefs before they ship. Not to replace judgment – just to catch what gets missed when everyone’s moving fast.

The Principle Behind the Fixes

Every workflow fix comes down to the same idea: remove decisions that don’t need to be made.

Most friction hides in ambiguity. When people have to guess what’s expected, they hesitate and make assumptions that turn out to be wrong.

Clarity fixes that.
Clarity is a form of kindness.

You’re not optimizing for speed, by the way. You’re optimizing for focus.

The goal isn’t to make people work faster. It’s to stop wasting their attention on things that shouldn’t require it. That’s how you protect creative energy over the long haul.

If You Don’t Own the Workflow

Maybe you’re not the one who sets the process. Maybe you’re a middle manager, or a senior contributor, or someone who sees the problem clearly but doesn’t have the authority to fix it unilaterally.

Here’s how to make the case.

Don’t lead with complaints. Lead with cost. Frame the friction in terms of what the team loses: time, quality, morale, momentum. Make it concrete.

And don’t propose an overhaul. Propose a pilot. One specific fix. Two weeks. A clear way to measure if it helped.

(If you need a refresher on setting goals that actually work for creative teams, that’s a good place to start.)

Make it easy for the person with authority to say yes.

Small wins build trust, and trust builds room for bigger changes later.

The Quiet Work

Fixing workflows isn’t glamorous. It doesn’t make for a great leadership headline. Nobody’s going to write a case study about how you improved the creative brief template.

But when you remove friction from someone’s daily work, they feel it. Even if they don’t say anything. Even if they don’t fully realize what changed.

That’s the kind of care that compounds.

It doesn’t announce itself. It just makes everything a little easier, day after day, until the team wonders why things feel lighter than they used to.

That’s workflow love. It’s not loud. But it’s real.

Want to dive deeper into the principles that make copy actually work for your team?

I’ve distilled 20+ years of marketing expertise into a free micro-course called The Minimalist Copywriter’s Playbook. It covers the 5 core principles I use every time I sit down to write – ones you can apply immediately.

Grab it here →

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 113th 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 much more!

In this week’s issue:

• Copy Tip: Every sentence should earn the right to exist

• AI Tip: Build “Why Layers” Into Your Context (Not Just Examples)

• Ai Doesn’t Reduce Work, It Intensifies It (via HBR)

• Welcome Flows Are Dead. Entry Flows Are Thriving. (via Astral)

• Leading Brands Win on Consumer-Perceived Value (via Branding Strategy Insider)

• Authentic Emotion in Marketing: Going Beyond Valentine's Day Clichés (via The Copy Minimalist)

• Video Pick: Marketing Legend: The True Future of AI in Marketing

• Swipe File Additions

• Job Opportunities

Copy Tip of the Week

Every sentence should earn the right to exist

Most copy doesn’t fail because it’s bad – it fails because it’s unnecessary.

Mid-level writers tend to stack sentences that sound fine but don’t do anything. They flow well, but they don’t move belief, reduce friction, or increase clarity.

They’re dead weight.

A sentence earns its spot if it does at least one of these:

• Moves the reader closer to a decision

• Removes a doubt, fear, or question

• Sharpens understanding of the offer or outcome

• Increases trust or perceived competence

If it doesn’t do one of those, it’s probably indulgent.

How to apply it in practice:

When editing, don’t ask “Is this good?”

Ask “What job is this sentence doing?”

If you can’t name the job in plain language, cut it or merge it with something that has a job.

This is especially important in intros that warm up too long, feature explanations that repeat themselves, or transitions that exist just to sound polished.

Imagine you’re paying per sentence.

Would you buy that one?

AI Insight of the Week

Build “Why Layers” Into Your Context (Not Just Examples)

Most teams show AI what worked:

“Here are our best ads.”

High-performing teams teach AI why it worked:

“Here’s why these ads won.”

How to apply it:

For every winning example in your brand context, add 2–3 quick notes:

• Why it worked

• Which objection it neutralized

• What audience belief it leveraged

Now the model isn’t just copying patterns — it’s learning how to think through creative decisions.

Must-Read Articles

Ai Doesn’t Reduce Work, It Intensifies It (via Harvard Business Review)

🔗 https://hbr.org/2026/02/ai-doesnt-reduce-work-it-intensifies-it
Why I recommend it:
This piece from Harvard Business Review makes the smart point that AI doesn’t magically shrink your workload — it often expands it unless you define precise use cases and stick to them, because without intentional boundaries you can easily trade human judgment and decision-making for busywork, not better work.

Welcome Flows Are Dead. Entry Flows Are Thriving. (via Astral)

🔗 https://weareastral.co.uk/thevault/welcome-flows-are-dead.-orientation-flows-are-thriving
Why I recommend it:
Reframes welcome flows as “orientation flows” that prioritize the customer’s actual experience and needs first — a mindset shift that helps you design journeys that feel helpful and human instead of purely transactional.

Leading Brands Win On Consumer-Perceived Value

🔗 https://brandingstrategyinsider.com/leading-brands-win-on-consumer-perceived-value/
Why I recommend it:
Argues that the brands that consistently win aren’t just selling features or prices — they’re shaping consumer perceived value in a way that transcends industry or vertical, reminding us that how customers interpret your product’s worth often matters more than the product itself.

You Might Also Like:

LEVELING UP WITH ERIC SIU
Marketing Legend: The True Future of AI in Marketing
📺 Watch on YouTube

Why I recommend it:
In this conversation, Seth Godin joins Eric Siu to unpack ideas from This Is Strategy, reframing strategy as a long-term compass rooted in empathy, systems thinking, and infinite games, while arguing that in an AI-driven world, the real advantage comes from consistency, judgment, and telling true stories that build trust over time.

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

Pretty Fly Copy

MUDITA

Format: Email
Why I like it:
Love the idea behind this email – it’s about presence not presents. It was captured well in the headline toward the bottom of the campaign: “This Valentine’s Be Present, Not Just Together.”

FREE FLY APPAREL

Format: Email
Why I like it:
If you’ve been following me for some time, you know I love a good theme. This campaign (and its product feature) is geared toward anglers (fishermen/women). What’s powerful about it is the product feature callouts are things an angler would care about (I know because I am one and am thinking about the guide pants!).

TASTESALUD

Format: Facebook Ad
Why I like it:
Super simple ad, which just adds to the notion that “less is more.” In particular, I liked the headline in the bottom of the ad: “Hydrate. Protect. Repeat.” It does a good job conveying the benefits and simplicity of the product.

Career Opportunities

These remote opportunities are updated every week with copywriting and marketing roles ambitious job-seekers should definitely apply for. 

Brand Copywriter (Contract; Part-time) at Huckleberry Labs
📍Remote ℹ️ SaaS/B2C 💸 $40 - $55/hr (USD)

Marketing Copywriter (Contract; Part-time) at Huckleberry Labs
📍Remote ℹ️ SaaS/B2C 💸 $40 - $55/hr (USD)

Senior Copywriter at DTN
📍Remote ℹ️ B2B 💸 $71,000 - $95,000/yr (USD)

Content Marketing Managers & Strategist at Novora
📍Remote ℹ️ B2B 💸 $85,000 - $105,000/yr (USD)

Copywriter at Unreal Snacks
📍Remote ℹ️ CPG/B2C 💸 $100,000 - $120,000/yr (USD)

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

✌️
Matt

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