Copywriting Friday: It’s what you don’t know that hurts you

Published: January 2024

Copywriting Friday highlights the tools and techniques of persuasive content. Some of the examples may seem dated, but the principles are timeless (and critical for conversion rate optimization). Enjoy.

Here’s the back of an envelope from the mid-1990s. It contained a promotion for the 3rd edition of a book called The Truth About Money.

But forget the book; the envelope alone is a tiny masterclass in copywriting.

The back of the envelope.

The envelope reminds us of the advice that copywriting legend Gary Halbert gave Dan Kennedy (as featured in The Ultimate Sales Letter).

“Picture the person you’ve sent your sales letter to with a stack of mail in their hands, sorting through that stack, standing next to a wastebasket.”

Times may change, but humans and marketing principles rarely do. Although we might now imagine stuffed email inboxes or scrolling through social media, the first job of copywriting is the same as ever. Be noticed.

How does this envelope capture and keep, and leverage attention?


It begins with a one-word headline that everyone cares about:


How could you read this on an envelope addressed to you and not proceed to the next line? Impossible, especially given what’s coming next:

It’s what you DON’T KNOW that hurts you…

In eight words, the copywriter conjures fear, curiosity, and expectation—especially for more mature people struggling with their finances (the target market). It’s careful framing for the bullets that follow:

  • YOU KNOW credit cards are a major cause of debt—but do you know the TWO EASY TRICKS that help you pay off your credit cards each month?
  • YOU KNOW Social Security benefits can be yours at 62—but do you know when it makes sense TO WAIT LONGER?
  • YOU KNOW that bills must be paid—but do you know WHO YOU SHOULD PAY FIRST BEFORE you pay a single bill?
  • YOU KNOW interest earned on money is good—but do you know THE KIND OF INTEREST that multiplies your money and leads to financial independence?
  • YOU KNOW people who say investing is too risky—but do you know THE “D” WORD THAT REDUCES RISK to the absolute minimum?
  • YOU KNOW that insurance is a must—but do you know the kind of insurance you should NEVER, EVER BUY?

Writing “fascinating” copy

Copywriters call these “fascinations”—bullets that blend benefits and curiosity into a powerful cocktail. In this case, each bullet hints at things we don’t know about money (curiosity) and what we’d get if we did know (benefit).

Even if you aren’t the target audience… can you feel the tension of not knowing? It’s the same tension that marketers use every day to get you to scroll down their webpages. Look again—each bullet is really a headline.

The fascinations are also written parallel. Each one has:

  • A similar length.
  • The words “YOU KNOW” at the beginning.
  • A “—” at the center.
  • The words “but do you know” at the start of the second clause.
  • A bolded section of 3-6 words.
  • A question mark at the end.

Fascinations can be written in different ways, but the copywriter is creating a specific effect here. As well as the curiosity and benefits, they are building a rhythm, a drumbeat that leads to the final line on the envelope:

OPEN NOW… because it’s about time you knew THE TRUTH ABOUT MONEY!

This is the call to action.

Everything above is in service of this goal—getting the prospect to open the envelope.

Think about what’s happened here. The copywriter has engineered huge tension within the target market, only to offer an easy (if temporary) release to that tension.

Open the envelope!

Then, of course, the dance begins again.

Watch out for our next Copywriting Friday article, where we’ll venture inside the envelope.

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