The closer I am to my own work, the more literal my copy gets. Here’s how I catch it.

I have one rule I hold myself to with every client I work with. I don’t tell anyone to do something with their brand that I wouldn’t do for myself. If I’m asking someone to cut the jargon and say the thing plainly, I’d better be doing the same on my own homepage.

Following that rule sounds easy. In practice, the copy I struggle with most is my own. I can read a stranger’s website and see the problem before my coffee cools. When I read mine, I read what I meant to say, and I skim right past what’s actually on the page.

The problem I find most often, in my work and everyone else’s, has a name that’s been around for decades.

The Drill and the Hole

There’s an old sales line that says people don’t buy a quarter-inch drill because they want a drill. They buy it because they want a quarter-inch hole. Harvard marketing professor Theodore Levitt made the line famous, though he credited it to an ad man named Leo McGivena.

The point is simple. Buyers care about the result. The tool is just how they get there.

Most of us still write about the tool. We list the features, explain the process, and describe how carefully we built the thing. A coach writes about her six-step framework when the reader wants to stop dreading Monday. A creator describes his editing setup when the viewer wants to learn something in ten minutes. A shop owner lists materials when the customer wants a gift that makes her sister cry a little.

None of that information is wrong. It’s just in the wrong order, and the reader won’t do the work of translating it for us.

Why We Get So Literal

The closer you are to your work, the more literal you get. You know every decision behind it, so the details feel important. You remember how long the hard parts took, so you want credit for them. And you’ve explained it so many times that the outcome feels too obvious to say out loud.

There’s research that backs up how hard it is to see our own situation clearly. In a 2014 paper in Psychological Science, Igor Grossmann and Ethan Kross found that people reason more wisely about other people’s problems than their own (read the study). When participants thought about a friend’s conflict, they showed more humility and saw more points of view than when the conflict was theirs. When people looked at their own situation the way an outsider would, the gap closed.

The study was about relationships, not marketing. Applying it to copy is my own stretch, but I think it fits. When it’s someone else’s homepage, I’m the outsider, and the drill copy jumps out at me. When it’s mine, I’m standing too close to notice.

Write the Standard Down

My fix was to stop trusting my gut in the moment and write our copy standards down in one place. That way every writer on our team, people and AI, works from the same playbook, no matter who the piece is for.

The rule I come back to most is the fifth-grader test. If a fifth grader read the headline, could they tell what they’d get? If the answer is no, it’s still drill copy.

Here’s the part that surprised me. I found drill copy in my own work over and over, and I only caught it because I held myself to that same written standard. If I’d left myself out of the rules, I would have missed it.

A written standard works because it gives you distance on demand. You don’t have to feel like an outsider. You just have to check your work against something that was written before you got attached to the draft.

How to Catch Drill Copy Today

You can try this on your own headline in a few minutes.

Read your headline and ask what the reader gets. If the answer is a feature, a process or a description of you, you’re looking at the drill. Write down the result someone would actually notice in their life or business.

Explain it to a fifth grader. Say the outcome out loud in one sentence a kid would follow. That sentence is usually closer to a good headline than anything you wrote at your desk.

Borrow outside voices. I follow Dan Martell’s content and the Maverick AI newsletter closely, and I hold my own positioning up against what they’re saying to see if it still makes sense. People with no stake in your feelings are great at spotting what you skipped.

Let AI do the first pass. Paste your homepage headline and first paragraph into ChatGPT, Claude or Grok. Ask it to point out every place where the copy describes the product or how it works instead of what the reader gets, then rewrite it so a fifth grader would understand what they’d gain. Keep what sounds like you and toss the rest.

The Hole Is the Headline

Your process matters, and your features matter. They just belong further down the page, after the reader already knows why they should care.

So pull up your homepage and read the first line. Ask yourself whether it’s describing the drill or the hole. If it’s the drill, you know what to rewrite this week.

If you want more on why your own voice matters so much to a brand, I wrote about it in Why Most Executive Brands Die Before They’re Built.

And if you want one idea, one AI tip and one episode in your inbox every week, join The Tribe List.