The big difference between experienced Marketers and newbie Marketers?
Experienced ones have made waaaaaaaaaay more mistakes.
To get good at something, you have to mess up—a lot. And even the brightest Marketers sometimes end up on the naughty list. 🪨
That brings us to today: if you’ve been following along, you might remember the ask to submit your most chilling Marketing Nightmares.
Now, we’re sharing a few of these thrilling tales to warm your cocoa AND to remind you that every nightmare comes with a gift-wrapped lesson you can hang on your tree next year. 🎄
So settle down by the Yule Log, pour your favorite festive bev, and be prepared to develop some new Marketing fears for 2025…
P.S. Got a Marketing nightmare of your own? Submit it here! Always anonymous, always treasured.
P.P.S. Stories have been edited to protect Marketing Bestie anonymity, and for a little holiday pizzazz...
1️⃣. The Cease & Desist That Stole Christmas
Our first tale comes from a reader in a snowy land where the only thing colder than the weather is the heart of legal teams…
We begin in the shadow of NFL stadium “Reindeer Field,” where a bustling local ad agency crafted its wares.
There, a newly-minted Marketing elf named Noel Twinklefluff started her very first Marketing job. The first task? Promote a nearby event space for pre-kickoff tailgates. (Festive!)
Without Marketing experience but with a sleigh full of ambition, Noel got creative, whipping up some sick social graphics in canva the workshop.
Armed with glittery content (featuring borrowed team logos), she was convinced her socials were the most magical in the land. “SURELY,” she thought, “tagging the team and citing my sources will keep the Grinch—I mean, the lawyers—at bay.” *cue scary minor chord*
Can you guess what happened next?
One snowy morning, the workshop received a Cease & Desist that curdled everyone’s peppermint mochas: the ACTUAL legal team for the ACTUAL NFL franchise were demanding takedowns…or else.
Convinced her budding career was over, Noel apologized to everyone—the client, her boss, even Big Red himself. And of course, she deleted every flagged post faster than a snowflake melting in a toasty open fire.
Thankfully this tale of woe ends with joy: Noel’s career (and her spirit) lived to tell the tale—a Christmas miracle!
Remember dear readers, in the icy tundra of intellectual property, even the most pure & bright mistakes can summon a blizzard of consequences…brrrrrrr!
2️⃣. Automation Avalanche
Our next tale comes from a reader whose story will haunt me—and my CRM audits—for years to come.
Late one evening, Buddy the Marketing Elf was training a new recruit on how to send a TARGETED “thank you” email to a small group of donors who had recently been contacted by phone.
By careful candlelight, Buddy and his trainee set up a festive email they were sure would delight their carefully-curated list. Before clocking out at the workshop, Buddy even reviewed the send again before scheduling it to launch the next morning.
Little did Buddy know, there was a mischievous holiday imp lurking in their CRM. 😈
It turns out, reopening the setup stream had RESET the recipient list…to every single person on their email list. And the next day…over half a million inboxes jingled with an email meant for just a few hundred.
Here’s what Buddy told us:
“At 8 a.m. sharp the next morning, I got the email.
I wasn’t supposed to get the email.
In fact, over half a million people were very much not supposed to get the email.”
The fallout was instant—and hilarious. For people who hadn’t spoken to the nonprofit, getting a mysterious personalized email felt as creepy as a mall Santa who’d memorized your wishlist.
But in a twist straight out of a Hallmark movie, their “oops” email follow-up raised $30,000, and had the highest open rate of the year.
Moral: even the most chaotic flubs can sprinkle a little holiday magic—if you’re lucky, and move fast.
3️⃣. A Blizzard of Bad Decisions
Our final tale comes from a reader caught in a never-ending loop of corporate chaos.
Our hero: Rudy the elf, a weary Marketer yearning for a singular vision for his team.
The villain: a shadowy cabal of senior executives with a lot of opinions...but no Marketing experience. (Sound familiar??) 😱
You see, at THIS Christmas workshop, everything the elves made had to be reviewed by FIVE different executives before it could be loaded into Santa’s sleigh.
And one snowy night, in the middle of a massive rebrand, their nitpicking claimed a victim: the CMO elf threw down their tools and quit because of all the inefficiency and lack of trust.
It was a tough day. The CMO had always been a voice of reason, and no one was left to protect the rest of the workshop from Executive Micromanagement.
But Rudy and the rest of the elves pressed on, somehow launching the site in time for Christmas shopping promotions.
But when the site went live, there was a blizzard of glitches. Not only were there broken links and terrible copy….sales were CRATERING. It was a true nightmare before Christmas.
It was so bad, Rudy and the other elves had to work through the holiday, putting out all the customer fires with nothing but eggnog-fueled determination.
The most chilling part is the epilogue: a year later, the whole team was back to the drawing board, doing ANOTHER redesign and wading through the same problem: too many senior elves in the workshop.
It's a haunting reminder that sometimes the scariest part of a project isn’t the work itself—it’s the people telling you how to build the snowman.
