Three weeks into COVID in 2020, I got a creative brief from Tinder. 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. It won my first Telly award.
It worked because the team walked into a room of nervous clients during a very scary year and pitched something that was not brand safe. We believed this idea would work, and we pitched it that way.
Curiosity
The best professional decision I made across ten years working on Nike, Meta, Levi’s, and Tinder was letting myself go down rabbit holes I knew were going nowhere.
Your algorithm shows you content it thinks you want to see. You 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
Last summer Bad Bunny announced a thirty-show residency and did all of it in Puerto Rico, for residents of Puerto Rico. He closed the run on the anniversary of Hurricane Maria. He could have done thirty shows in thirty countries and made considerably more money. He didn’t, because he cared about a specific place and a specific group of people. The residency brought millions into Puerto Rico and became one of the defining cultural moments of the year.
One of the products I sell is my commitment. The specific things I care about are not a limitation. They are the only reason my work looks different from the work of the very large number of people who can technically do my job.
The market does not reward generic. It rewards specific.
Aloofness is the opposite of that. Being too-cool-to-care, acting like you are above the thing you are being paid to make. It reads as sophistication and is the most replaceable quality you can bring to a creative career. The supply of people too cool to try is infinite. Be the one who walks in and says I love this, and here’s why.
The Boring Brief
What if I ended up writing subject lines for a regional insurance company? What if I didn’t care about the product even slightly?
I think Flo is a good reference when you’re stuck in this line of thinking. 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. A name, a vibe, a whole store of coworkers. Then Stephanie Courtney showed up and committed to the bit for almost twenty years.
Not every brand will let you do that. But you can almost always find five percent of the brief you can actually love. The small piece of humanity inside the boring product. You find it before you walk into the room, and then you make it yours.
I’ll be honest about the limits. I have worked with brands I disagreed with and people who wanted me to fail. Sometimes I showed up anyway. Sometimes 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
Northern Arizona University, April 2026:
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.
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