Every marketer has a highlight reel: The campaign that converted, the launch that killed it, the perfect subject line that got a 68% open rate. We talk about those a lot.

What we don’t talk about as much?
The ones that didn’t land.
The messages that fell flat, got misinterpreted, or just made everyone say “eh.”

I’ve had those moments. We all have. And as frustrating as they are in the moment, they’ve taught me more about good communication than any win ever did.

Here’s what I’ve learned from the misses.

1. Clarity > Cleverness

I once helped draft an email campaign we were really proud of. It was witty, playful, packed with metaphors, and no one knew what we were actually offering.

We buried the message under a pile of creativity. It sounded fun, but it didn’t say much.

Now? I ask myself one question before I send anything out:

“If I skim this in under 10 seconds, do I know what it is about?”

If the answer’s no, it’s back to the drawing board.

2. Assume Less. Ask More.

There was a time I helped launch messaging for a global campaign. We’d tested the copy internally, reviewed it for tone and accessibility, and missed a cultural nuance that, in one particular region, shifted the meaning entirely.

It was a small phrase, but it changed everything.

Since then, I’ve learned to bring in local voices early. Not as a checkpoint, but as part of the creative process. The more perspectives at the table, the better your message holds up out in the world.

3. Feedback Is a Gift (Even When It Stings)

One of the hardest messages I ever sent was a stakeholder update that tried to “soften” some tough news. I got feedback that it felt vague and a little condescending.

Oof. That one stuck with me.

But it taught me a lot about tone, about owning mistakes, and about not underestimating your audience’s ability to handle the truth. Being direct isn’t cold, it’s respectful.

4. The Medium Matters

I once sent a long, nuanced explanation of a program change… via Instagram caption.

It didn’t go well.

Sometimes, the message is fine, but the format isn’t. Learning when to send an email vs. write a blog post vs. pick up the phone is part of being a good communicator. Not everything fits into 280 characters (and honestly, that’s okay).

5. Human Always Wins

When in doubt, sound like a person. Not a brand. Not a committee. Not a robot. A person.

Some of the most successful “fix-it” messages I’ve written after a miss have been the simplest: “We got this wrong. Here’s what we’re doing to make it right.” No spin, no jargon, just honesty.

People respond to that.

Final Thought

Communication will never be perfect. Context shifts. Audiences surprise you. Humans are complex. But that’s what makes this work so rewarding.

You won’t get it right every time. But if you’re listening, learning, and showing up with humility, you’re doing it right.

And the next time a message misses? Well, you’ll know what to do.