Three weeks into COVID in 2020, I got a creative brief from Tinder. Basically, they wanted a brand awareness campaign during a global pandemic.
The brief, stripped down, was basically: get people to use a dating app while making it physically impossible to date.
We pitched a campaign called Put Yourself Out There. The idea was that a pandemic could actually be a good time to use a dating app. You aren’t hiding behind a bar or behind small talk. You are a person alone in your apartment, connecting with other people alone in their apartments. There was nowhere to go, which left more room to show who you actually were.
It worked, and it ended up winning me my first Telly Award.
Curiosity
After doing this a while, my best work has been created when I was super unfocused. When I ended up goinf down rabbit holes and getting really disconnected from the actual brief.
My algorithm knows me (more than I know myself), and I know I have to break that on purpose.
Read a Substack about a stranger’s hyperfixation.
Open a fresh YouTube account and search as a different person.
Scroll weird Letterboxd lists.
Most of the time it pays off in nothing. Occasionally, it will hand you an idea.
Commitment
Bad Bunny’s Puerto Rico’s residency is such a cool case study in being ultra committed to something you care about. He did a 30-show residency in Puerto Rico specifically for residents of Puerto Rico. The last show landed on the anniversary of Hurricane Maria, and overall ended up bringing millions into Puerto Rico’s economy. He cares about Puerto Rico and the people of Puerto Rico, and made that statement loud and clear.
As a human person, one of the things I have to sell is my commitment. The reason I show up in scary and unfamiliar rooms and talk a lot about cool creative is that I care about the work I create (or pretend to care). A very large number of people can technically do my job, but not everybody is gonna show up and give it the oomph.
Aloofness works for some people, I think it’s hard to market. I’m not above the thing I’ve been paid to make. I’m not too cool to try. I am very much here, trying as hard as I possibly can.
The Boring Brief
But what if I ended up writing subject lines for a regional insurance company? What if I don’t care about the product even slightly?
I think Flo is a good reference. She has been in something like 150 Progressive spots since 2008.
Car insurance is arguably the most boring product in the American economy, but somewhere in Ohio a creative team sat in a room and pitched the idea that the insurance could be funny. This lady, Stephanie Courtney, has literally created twenty years of ads as this character, and now we all know her.
Not every brand is gonna let you do that, but I do think buried in most briefs is 5% of something that is actually creative. That’s the small piece of something to grab onto (even if it’s regional insurance).
I’ve definitely worked with brands I disagree with, and people who want me to fail. Sometimes I made it work, other times I left. Both are allowed, and only you know which one is right. But when the five percent is there, it is worth trying.
I say: Go down the rabbit hole, commit to the specific thing, walk into the room, and have some damn passion.
Xx, Caitlin
If you’re new here, I write a monthly serialized novel called Everything is Advertising, about a burned-out Creative Director and his cynical team that accidentally create QAnon through a viral marketing campaign. If you like that kind of thing, you can start at Part One and catch up from there.
Every Monday, Above the Fold breaks down what’s running in advertising, what’s landing, and what’s a total disaster.
Every Friday, The Business of Advertising shares lessons from over a decade working on the front lines of advertising.

