the messaging curse you didn't know you had


Hey, hey Reader,

Rush Week, 2004.

No TikTok. No outfit hauls. No synchronized dancing.

Just a bunch of nervous college girls in denim skirts and UGG boots, clutching their Coach wristlets and sweating through triple-popped collars and Juicy Couture perfume.

Anxiously wondering….Did I make the cut?

Back then, sorority rush didn’t include curated online personas or viral “fit checks.”

But one thing, one quote really remained constant (& was the IT sisterhood saying):

"From the outside looking in, you can’t understand it. From the inside looking out, you can never explain it."

This quote gnawed at me as I read Emma Stratton’s Make It Punchy.

Because once you get on the inside of an EdTech product, you’re screwed.

You lose the ability to see it through fresh eyes.

You know the product. Its features. Its strengths. Its brilliance.

But try explaining it to someone who knows nothing about it? Suddenly, you’re speaking another language.

Emma Stratton calls this The Curse of Knowledge, and she’s right. The more we learn, the more we forget what it was like to be a beginner, that Shoshin mindset.

When I started freelancing, I had a million questions:
What does copywriting actually mean?
What’s a value prop?
Why is everyone so obsessed with scales?

Now, those answers feel second nature.

But when you’re marketing an EdTech product to school admins and educators, forgetting to step back is a fatal flaw. That’s when messaging gets clunky, overly jargon-aited, and just… misses.

But, if you know you have the Curse of Knowledge, you can break free from it.

Here’s how:

  • Do market research consistently.

Not once. Not quarterly. Weekly. Stay sharp by constantly tuning into your audience’s words and challenges.

  • Talk to your all-star customers.

The ones who actually buy. Their insights will keep your messaging fresh and relevant.

  • Share your messaging with a total outsider.

Before you hit publish, run your copy by someone completely outside of EdTech (even better, speak it): your partner, your neighbor, or even a friend who isn’t in marketing. If they don’t get it, your audience won’t either.

If you need help with this, consider me your Shoshin-sherpa.

Hit reply and we can chat about your messaging.

And as always , I'm rooting for you 👏.

Kelly

PS. Wanna really know what your buyer's need before they do?👇

Join Inside the Inbox: Turn your B2B Emails into District-Winning Deals. Get on the waitlist now.

Want to Get Un-Stuck with Your Marketing Strategy? Book a 1:1 hour-long sesh with me.

Get Your Case Studies Noticed with Case Study Blueprint. Buy now.

Say👋 on LinkedIn

PS. Proof of yours truly...

Did a friend forward this email? Subscribe here.

191
Unsubscribe · Preferences

Inside the Inbox: Turn Your Emails Into District-Winning Deals

Strip away distractions and shiny objects to deliver the email marketing results you need in EdTech. If you're a customer success manager, a marketer, a copywriter, or a founder, every Wednesday get weekly tips to reach and genuinely engage school district decision-makers.

Read more from Inside the Inbox: Turn Your Emails Into District-Winning Deals

Hey, hey Reader, Let’s talk welcome sequences. Specifically, the role they play in edtech marketing. If you've ever googled "best welcome email tips" and found yourself drowning in B2C advice ("Add urgency!" "Offer a discount!" "Convert them ASAP!"), you're in good company. When you're marketing to schools and districts, a welcome sequence isn’t the same conversion engine you'll find in B2C. It’s a first hello in a very s l o w dance. Your reader likely can’t buy right away. They may not even...

Hey, hey Reader, I’ve been thinking a lot about customer newsletters lately. Specifically, the monthly kind that B2B SaaS & EdTech companies send out. I launched one this year for a client. It’s solid: a mix of educational content and product updates, thoughtfully written, well-designed, and genuinely useful. But now I’m getting the inevitable question:“How is it driving product engagement or activation?” And I’ll be honest. I’ve always been skeptical of monthly newsletters for exactly this...

Hey, hey Reader, I’ve been helping a client move from what I generously call an ESP to a real-deal platform. As exciting as it sounds, most of our time hasn’t been spent designing email flows or writing copy. It’s been meetings. About forms...and fields...and data. Specifically: Where the current data lives What’s actually usable How to prevent garbage data from creeping back in Funny enough, this week, I stumbled on a Slack thread that felt eerily familiar. Marketers and ops folks were...