An unexpected lesson that shaped how I write copy
Before I was a messaging strategist and copywriter, I was a teacher.
And if there’s one thing that prepared me for the work I do now, it’s this: To truly connect with someone, whether it’s a student or a buyer, you have to meet them where they are.
Not where you want them to be. Not where your system says they should be. And definitely not where your brand brief assumes they are.
These days, I do that by using deep customer insight, research, and real voice-of-client language to uncover what matters most.
But that skill didn’t start in business. It started in my second-grade classroom, with a student named Osvaldo.
👋🏻 Welcome to issue 53 of straight-to-the-point insights that turn why they buy into how you sell.
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What looked like resistance was something else entirely
He arrived in my second-grade classroom speaking maybe five words of English. He was reading in Spanish at a kindergarten level. Everything about his body language screamed: I don’t want to be here.
He wouldn’t make eye contact. He barely spoke. When I pulled out the standard reading assessments, he shut down completely.
A lot of teachers would have labeled him resistant. Or worse, lazy.
But I didn’t buy it.
I knew what I saw in Osvaldo wasn’t refusal. It was overwhelm. It was frustration. And maybe most of all, it was the quiet disappointment of not being understood.
So I started digging. Asking questions. Watching what made him light up. And I discovered something small, but huge: he loved horses.
That’s where we started.
Relevance makes even the hard things feel worth it
Instead of handing him decodable readers about Jack and Jill or whatever the leveled bins said was “appropriate,” we built a whole vocabulary set around horse terms. Then I found books with horses on the cover.
Some were way above where he “should” have been reading, but that didn’t matter. I read them with him. I scaffolded the hard parts. I let him read the words I had taught him and the sight words we were working on.
And then I started catching him doing something I didn’t expect.
He wasn’t just participating. He was choosing challenge.
He’d go to the library or the reading corner on his own and pick up books that were way above ‘his level’.
Not because it was easy. Because it finally felt meaningful. That’s what relevance does: it gives someone a reason to try.
But not everyone saw it that way.
Why pain-based messaging backfires
One day, our class went to the library. Osvaldo walked up with a book in his hands, eyes bright, beaming. And the media specialist looked at it and said, “Sorry, you can’t check this one out. It’s above your reading level.”
I watched his whole body sink. His face fell. Shoulders slumped.
That one sentence, meant to help, shut the whole thing down. That’s what leveling does when it’s used as a limit instead of a scaffold.
But the next day, something happened. He walked over to the reading corner in our classroom, and there it was: that exact same book, front and center in the horse book basket. The joy on his face when he saw it—I’ll never forget it. That book wasn’t “too hard.” It was his.
The part that stays with me the most though?
His body did more than slump. It gave up. That’s what happens when people feel shut out of something that was finally starting to feel like theirs.
And we do the same thing in our marketing when we over-agitate pain points. We think we’re being persuasive, or helpful. But what we’re actually doing is triggering shutdown.
Shame doesn’t sell. And it doesn’t motivate or instill trust.
People don’t need to be reminded how bad it feels. They need to believe something better is possible.
Your audience isn’t everyone. It’s the ones who feel seen.
Now, I want to be clear. Osvaldo wasn’t the only student I had that year who was labeled “struggling.” I had three second graders who came in reading at a kindergarten level.
One of them made a year and a half of progress in a single year. And the other? Two years’ worth.
Not because I followed a rigid system or created wildly different ones. Not because I followed some color-coded strategy from the latest curriculum training. Because I listened.
They knew what they wanted.
I knew what they needed.
I found a way to give them both.
It wasn’t about treating them like three separate problems. It was about meeting each of them where they were, and helping them feel seen.
And maybe that’s the same mistake we make in both education and marketing. We assume different kids need totally different things. We assume different audience segments require entirely different messaging.
But often, the underlying need is the same: To feel understood. To feel like this (whatever “this” is) is for them.
That’s not differentiation. That’s connection. And that’s what makes growth possible.
💡 What if your message helped your audience move faster toward a decision? What if it built enough trust to shorten your sales cycle or double your revenue in the next year?
It’s not a guarantee. But it’s not magic either.
Your CTA’s not the problem (even if your conversions are)
We assume people aren’t buying because the offer isn’t irresistible enough, the CTA isn’t punchy enough, or the headline doesn’t “hook.”
But often, the real issue is this: We haven’t made it matter to them.
- We write to demographics instead of desires.
- We tailor our message to avatars instead of actual people.
- We segment endlessly, trying to say the perfect thing to each group. When what they really need is to feel seen, respected, and understood.
Because once your audience feels that?
They’ll give your message more space. Even if it’s long. Even if it’s simple. Even if it doesn’t follow every “best practice.”
Relevance builds trust. Trust builds momentum. And that momentum is what drives conversion, not gimmicks.
What that disconnect looks like inside your business
Misalignment in your messaging doesn’t always look like a broken headline or weak CTA. It often hides in your day-to-day business problems.
- You’re getting traffic, but conversions are flat.
- You’re attracting the wrong leads. Or worse, being ghosted after discovery calls.
- You’re stuck relying on referrals.
- People keep asking, “Wait… what do you actually do?”
- You’re piling on tactics: tweaking headlines, rewriting CTAs, launching promos—but still not seeing results.
- You’re trying to appeal to everyone… and connecting with no one.
- Your team or collaborators are confused, or describing your business inconsistently.
These are symptoms of a deeper issue: messaging based on assumptions and outdated tactics, not relevance.
Why research is an ethical act
I also believe there’s an ethical responsibility to doing this kind of deep research. You’re asking someone to trust you. To buy from you. To act. That’s a big ask.
And if you haven’t done the work to understand their context, motivations, and what really matters to them, then what are you actually writing for?
Writing without research might get clicks. But it won’t build trust. And it sure as hell won’t build a message that respects the people it’s trying to reach.
What makes my approach different
This isn’t surface-level research. I don’t just check boxes or skim testimonials.
- I ask better questions. I follow the threads. And I listen for what people aren’t saying. Because that’s where the real insight lives.
That’s the difference between copy that sounds good and copy that actually works.
When you hire me as a copywriter, you’re not just hiring me to make your words sound good. You’re hiring me to do a very specific job: to move the right people toward a specific action.
On your website, that might mean helping someone go from “just browsing” to booking a discovery call.
On a sales page, it might mean helping them feel confident enough to sign up for your course or membership.
Either way, the goal isn’t just to attract or engage; it’s to guide. And you can’t do that if you don’t know who you’re writing for.
I wouldn’t recommend a book to someone without learning a little about what they like. So why would I write copy before I understand what your audience actually cares about?
Relevance isn’t about optics. It’s about understanding.
When I started sharing what was working with Osvaldo, I got a lot of well-meaning suggestions from other teachers. Things like, “He’s from Mexico, right? Try getting him books about Mexico.”
The intent wasn’t malicious. But the assumption was shallow.
Because if I moved to another country, I wouldn’t want to read a book just because it was about the U.S. I’d want a book that made me feel something. A story that reflected who I am, not just where I’m from.
Relevance isn’t about cultural tokens.
It’s about curiosity, belonging, and the choice to treat people as whole, complex humans. Not categories.
What Osvaldo taught me about copy
Osvaldo didn’t need simpler content. He needed something that felt worth struggling through. He needed someone to see him, believe in him, and meet him where he was.
That’s what made him want to read.
Your audience? They’re not that different.
They don’t need louder marketing. They need messaging that feels personal. They need a reason to care, and a brand that actually sees them.
The problem usually isn’t your CTA.
It’s that your audience doesn’t feel seen. Relevance isn’t extra. It’s the reason people care.
When your message reflects their reality, you don’t have to push. It pulls.
Not sure if this applies to you?
If your audience feels unclear, hesitant, or disengaged, your message might be missing the mark. Not because it’s wrong, but because it’s not relevant enough. The moment your message reflects their world, everything starts to click.
Today’s actionable advice:
If your copy’s not converting, start by asking: Is it relevant enough to feel personal?
💡If your copy isn’t connecting, it’s not your fault. But it might be time to stop guessing and start listening differently. This is exactly what I help my clients do. And if it sounds like what you need, I’d love to talk.
🎙️Upcoming Interviews and Workshops
🗓️ You’re not going to want to miss this. I’m going live with Wendy-Shore Rosano on June 18th @ 11am EST. We’re talking about The ROI of Content: It’s Not What You May Think.
🎉 The Fun and Profitable Interview Series: Wendy and I talked all about the behind-the-scenes of building a business that doesn’t just look good, but actually feels good to run.
I shared some of my favorite lessons, some mindset shifts that changed the game for me, and what makes my business actually fun (even when things get messy).
Until next time,
Stacy
When you’re ready, here’s how I can help:
🔍 Strategy session: Messaging SOS for when you're stuck, second-guessing, or spinning your wheels. In one focused hour, we’ll pinpoint what’s not landing. So you leave with clarity, confidence, and a plan. Book your strategy session
📝 Copy audit Your words, but stronger. I’ll review your website, sales page, or emails and tell you exactly what to fix (and why). So your copy actually converts. Get your audit
✍️ Need help with your content creation? I have a HUGE announcement coming in 3 weeks! 👀
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