I genuinely struggle with annoying people.

I’m much more likely to hedge on not bothering you than risk annoying you. But the older I get, the more I realize: returning to my roots of being an annoying little sister has its advantages.

I’m the third of four. My older sisters were convinced I was the most annoying thing to walk the earth. The only way my parents could redirect that energy? Sports. I had too much of it—and if left alone, I’d just channel it into bothering my sisters. Endlessly.

I also insisted on doing everything they did. They were three and six years older than me, but I couldn’t accept that they got to play basketball and I didn’t. So my dad walked into the YMCA and begged them to let me play a year early—because I was that annoying.

(Yes, I shot at the wrong basket once. Still scored more than most of those girls. Worth it.)

Here’s the sales lesson: you’re only annoying if you don’t bring value.

I have “Owner-CEO” in my LinkedIn headline. If you know, you know: it’s a magnet for the most templated, zero-context, me-me-me outreach on the planet. It falls into two buckets: dev shops and sales/marketing agencies.

Most of them? Useless. Not because of the volume—but because they’re entirely about themselves.

“I offer X.”
“Just checking in!”
“Did you miss my message?”

No, I didn’t miss it. I’m ignoring you because you’re wasting my time.

But when someone leads with something I care about—when they’ve done their homework, when they’re genuinely solving a problem—I don’t care how many times they follow up. It’s not annoying. It’s relevant.

That’s the bar.

When I was building my startup, I printed out a photo of one of our earliest ICPs—let’s call her Gretchen—and taped it above my laptop. Every single thing I built: email copy, ad creative, training scripts, messaging frameworks… I did it with her in mind.

I didn’t guess. I didn’t generalize. I stared at Gretchen and asked:
How can I add value to her life today?

That’s the level of specificity your messaging needs.

I don’t care if you’re sending mass emails or 1:1 video messages. I don’t care if it’s a product launch or a cold open. If it doesn’t speak to the person it’s meant for—and I mean really speak to them—it’s noise.

If it does? You can follow up five times, post every day, send the same message twice in a week.

Because when you’re bringing value, you’re not being annoying.
You’re just doing your job well.

Now if someone could just explain that to my sisters.