I had it half-written in my head. Storyboard a short film a five and three-year-old could shoot. Six scenes. Teach framing and motion along the way. Twenty seconds of typing and I’d have had a clean little plan to hand my daughters, complete with shot angles and a suggested color palette.
My hand was already drifting toward the keyboard. Then it stopped, the way you stop at the top of the stairs when you’ve forgotten why you climbed them.
So I ripped the back cover off a coloring book (because we didn’t have any scrap paper). Markers that had mostly given up. A ruler none of us had patience to find, so the frames came out crooked. By the time we finished the first scene, one of six, I felt a strange low hum of guilt that I had even considered the other version.
I want to be precise about the guilt, because it surprised me. And quite frankly, this is therapeutic.
It wasn’t that I’d almost robbed them of something. They’d have been fine either way. It was that I’d almost robbed myself of something I didn’t know I needed until it was already happening. The arguing about what object Emree should have in her frame. The bad ideas that made us all laugh. The slow, inefficient, irreplaceable feeling of a few people making a thing that did not exist before they sat down.
Now here’s where I’ll defend the machine, because I’m not a purist and I’ve seen it earn its keep.
I ran win/loss software that leaned on AI to generate interview questions and talk to prospects and customers. And it worked. It pulled data we could actually act on, at a volume and consistency I could never have hit by hand. That was the right call. That was the boring, necessary, high-volume eighty percent of the work, and handing it to a system was not a betrayal of anything. It was good judgment.
But the line I carried into every meeting after that did not come from the software.
It came from an IT director sitting across the virtual table from me, talking about a tool his company had finally adopted. He said, “It was finally something that didn’t make me want to vomit.”
I have quoted that man in many-a-meeting. It resonates so thoroughly every time.
No survey produced it. No model would ever generate it. Ask an AI to write customer praise and you get “intuitive,” “seamless,” “a game-changer.”
You get the center of the bell curve, sanded smooth. You do not get nausea reframed as a compliment.
That sentence was too specific, too a little bit gross, and too true to have been predicted by anything optimizing toward the average.
That’s the whole thing, and it’s a marketing point as much as a parenting one. A model’s job is to find the mean and return it to you, fast and clean. But the mean has never sold anything memorable.
The line that closes the deal, the detail that makes someone trust you, the moment that sticks, those all live in the outliers. The weird specific real ones. And outliers are not something you retrieve. They’re something you make, usually by hand, usually inefficiently, usually in the part of the work you were most tempted to skip. (It makes me think of a sales leader I heard the other day say “You don’t want your prospect-facing reps prompting, you want them selling!” Which, what I heard is you want them being the human outlier in the sales process.)
The messy parts and the important parts keep turning out to be the same parts.
Some people will tell you the mess is the whole reason any of it is worth doing. I’m starting to think they’re right.
Stay Positive & Crooked Boxes Might Just Contain The Best Ideas
