3 Keepers & a Regret: Laurel Cummings
She makes brands funny for a living. Here's what she'd never let go of — and the one thing she was smart to dump.
3 Keepers and a Regret is a recurring series on Retail Therapy on Substack where I ask people I admire to name 3 things they’d fight to keep — bought, inherited, stolen — and 1 thing they regret.
In my heart of hearts, I’d like to be a humor writer. I can say funny things, but I’m not good at exaggerating to the point of absurdity, which is often needed in comedy. I find truth stranger and more interesting than fiction. Especially in the nitty gritty details of life. The former reporter in me likes to dig.
Laurel Cummings actually does funny — for a living. I don’t remember how I came across her, but when I did, I became obsessed, a bit, and wanted to know every detail of her job life. Not in a creepy “call the authorities” way. But, if you’ll sit down with me I’ll ask you questions for days, kinda way. Laurel lands a one-liner, every time. And she does comedy IRL. Which I would never.
Laurel also writes comedy — with pieces in places where I can’t get published, including McSweeney's. On Substack she shares industry news, trends and writing jobs. Anyone who’s sharing gigs where writers get paid real money to be funny is basically a God in my book.
As Founder and Creative Director of Free Puppies, Laurel helps brands find their funny bone — and proves humor drives revenue. And she isn’t joking. As for the free puppies, who doesn’t want them? Probably anyone who’s had them recently and isn’t ready for another. But, when not a lot out there is fun or funny, bring it. Please.
Three Keepers
3 things you’d fight to keep — bought, inherited, stolen
No. 1 — My SNL tickets
From 2009-2012, guests of the cast and writers at SNL reported to the illustrious “Laurel’s Line” on the lobby floor of 30 Rock to wait for a brutal tyrant to check their name on a clipboard, give them their show tickets, and have a trembling intern lead them through security up to Lorne Michaels’s office, cast dressing rooms, or the real party, the writers’ room. That tyrant was me and I kept one ticket from each show. They live in a bag in my home office to remind me that I once didn’t recognize the Coen brothers and Ed Norton complimented my f-me Louboutins.
No. 2 — Gold disc button necklace
My great-grandfather lived in a version of Chicago where, when it was a REAL party, men wore white tie with fancy ass buttons. When my grandmother passed I inherited a dozen or so of such buttons. Each is a flat gold disc topped with a diamond. My dad had them put on a gold cord so I can wear them as a necklace for my REAL parties, which I hope to have someday. Right now my social roster is mostly toddler Storytimes at public libraries.
No. 3 — Phone
My phone, because it’s a major organ I use more often than my liver (I’m sober).
One Regret
now the regret
During Covid I felt that if the world was probably ending, and I was a hardworking, single 30-something writer and woman, I may as well go down owning property. I bought a house I couldn’t really afford, but guess what? The damn world bounced back! Wait, a mortgage is how long?! Eff! I actually sold that house yesterday and now I can get my boobs done. Kidding! Save for college, of course. America!
Why I’m Still Shopping
I’ve never forgotten a quote from someone in the beer business when I was a reporter: “You can laugh with a beer or cry with a beer.” Clearly Laurel is choosing to laugh, just without the beer.
Memories come in all forms, from pieces of paper to a hand-me-down necklace made from buttons with diamonds. Laurel proves that truth is way more interesting than fiction.
I write a lot about money and the surrounding decisions. Rarely does someone own a choice that didn’t add up for them financially. I’ve met too many people who are house rich and cash poor. They suffer, refusing to make the change that would make life doable. Laurel made the bold decision and sold the house. I want to celebrate this and throw her a roller skating party. Although that’s how I busted out my front tooth in fourth grade. So maybe not.
Alas, Laurel and I aren’t the same. I live in flats and can’t stomach a heel taller than 2 inches, and even that’s a stretch most days. Her fantasy is to be in the “What’s In My Bag” feature in US Weekly. I fear showing up as a fashion “Don’t” in Glamour. Which is why I will probably be forever shopping, trying to feel like I got it right.
Huge thanks to Laurel Cummings of Free Puppies, which comes out twice a week full of comedy news, jobs, trends, and gossip!
When life stops making sense, we shop. More soon.
