"Don't make it awkward in second period" (do this instead)


This is the 181st Fundraising Writing Newsletter. If you find value here, please tell a fundraising friend. (Your fundraising friend can ​subscribe here for free.)

Wednesday, October 22, 2025

Hi Reader,

Brett and I are big Taylor Swift fans.

One reason: she's an amazing songwriter.

As writers, we none too seldom find ourselves appreciating one of her lyrics and raising an imaginary glass in tribute. Cheers, Taylor!

For example, from the song "Ruin the Friendship" on Swift's new album The Life of a Showgirl:

Don't make it awkward in second period

This line is great because it uses the familiar and the specific to quickly, efficiently convey meaning and feeling.

"Don't make it awkward" uses a common phrase that feels familiar (and therefore right) while hinting at the meaning of the song — which is that in high school it's all too easy to avoid taking a risk for love because it might "Ruin the Friendship."

"in second period" us a nicely specific detail to help you 'time travel' to the high school setting of the song; it also suggests potential: the beginning of the school day mirrors the beginning of a potential romantic relationship following from a friendship. You're left feeling the stakes.

It works in fundraising too.


"Don't make it awkward in second period" (do this instead)

In our most recent piece about developing your appeal letter "prime real estate", one key element we explored was the Johnson Box.

The Johnson Box is crucial.

Along with the outer envelope teaser (to get the envelope opened in the first place), the Johnson Box is the biggest, boldest, most important "headline" in your appeal letter.

When Brett and I are writing an appeal, we'll occasionally spend as much time nailing down our Johnson Box messaging as we will on the whole body of the appeal (especially for shorter, 2-page letters).

As the saying goes, "An error in the beginning is an error indeed."

So, make sure you get your Johnson Box just-so.

If you don't grab your donors right away, you're in danger of losing them right away.

Here's where you might take inspiration from Taylor Swift.

Example #1:

Familiar: taking a child to a nature center.
Specific: the baby's first word is "turtle."
Meaning: a nature center can change a life.
Feeling: how wonderful; I'd like to be a part of that!

Example #2:

Familiar: the concept of life turning on a moment.
Specific: "This could be your moment."
Meaning: I can really help this girl.
Feeling: I'm worried about her; what happened?!

Example #3:

Familiar: the notion of working hard and following the rules.
Specific: which didn't protect the senior quoted here.
Meaning: some seniors in need have been victimized.
Feeling: how awful, someone should do something; me...?


Simple approach, right?

Yes. But simple is not necessarily easy.

It takes practice.

I encourage you to practice combining the familiar and the specific to quickly, efficiently convey meaning and feeling so your donors keep reading and giving!


Fancy a little more lyrical inspo?

Here are 11 additional Taylor Swift lyrics you might ponder as you work on your fundraising writing — one from each of the other songs on her new album.

Each of them follow the idea above: familiar and specific for meaning and feeling.

From "The Fate of Ophelia":

Pledge allegiance to your hands
Your team, your vibes

From "Elizabeth Taylor":

Be my NY when Hollywood hates me

From "Opalite":

You were dancing through the lightning strikes

From "Father Figure" [POV of a villainous mentor]:

I can make deals with the devil
because my d - - k's bigger

From "Eldest Daughter":

Every eldest daughter
Was the first lamb to the slaughter
So we all dressed up as wolves and we looked fire

From "Actually Romantic":

And I know you think it comes off vicious
But it's precious, adorable
Like a toy chihuahua barking at me from a tiny purse
That's how much it hurts

From "Wi$h Li$t":

Got me dreaming 'bout a driveway
with a basketball hoop
Boss up, settle down, got a wish list
I just want you

From "Wood":

Seems to be that you and me, we make our own luck
A bad sign is all good
I ain't gotta knock on wood

From "CANCELLED!":

Did you girl-boss too close to the sun?
Did they catch you having far too much fun?

From "Honey":

You could be my forever night stand

From "The Life of a Showgirl":

Do you wanna take a skate
on the ice inside my veins?
They ripped me off like false lashes
And then threw me away

🎤 ✨


Randomly yours

For your brain, heart, and funny bone...

  • Fundraisingly InformativeThe Angels’ Share​ by Steven Screen (a fascinating blog post about how securing matching funds leadership donors is about more than providing an opportunity for doubling impact ... and that, like the trace whiskey that evaporates during distillation, the extra good done via matching funds amounts to "the angels' share."​
  • Appropriately Festive21 Facts About Throwing Good Parties by Angela Chen (a blog post with some interesting party ideas such as "Co-host parties with someone you like a lot but who isn't in your exact social circle, so that your two friend-sets can intermingle.)
  • Helpfully TaxonomicI stole this idea and now use it with every single employee​ by Alex Lieberman (an X post that categorizes 5 levels of work, starting with "There is a problem" and ending with "I identified a problem, figured out what caused it, researched how to fix it, and I fixed it. Just wanted to keep you in the loop.”)

Until next time: May you never so fear "ruining the friendship" with your donors that you avoid doing what it takes for a deeper, more rewarding relationship!

Grateful,

Julie Cooper & Brett Cooper
Fundraising Copywriters​
(and Cavapoo Charlie)
FundraisingWriting.com
100% human, thank you very much.

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