The Overthinker’s Dilemma (And The Day We Finally Hit Record)
This morning, I spun around in my chair as a visual hook for a social media video.
Not because it was a great idea, but because otherwise, I might’ve frozen.
And if you’ve ever tried to launch something you care about — a product, a post, a handmade anything — and suddenly felt like you couldn’t move, you’ll understand why I did it.
Overthinking never feels like fear; it feels like you’re being responsible, like you’re trying to do it right and you’re giving it the care it deserves. And so you wait, and tweak, and plan some more, and tell yourself you’ll start just as soon as it’s crystal clear in your mind.
We know this headspace intimately, because we work with founders who live here, and because we live here too. That loop of second-guessing doesn’t go away just because you know how to write a good headline or run a brand.
Sometimes you’re just a human trying to do something new, and new feels uncomfortable, especially when it means putting yourself out there.
We see it all the time with small-batch founders. You’re not some big corporation: your product is personal and you poured your heart into it. But now that it’s time to talk about it, everything starts to tighten. You don’t want to come across too polished or too casual. You want to be real, but you also want to be taken seriously. You want to tell the truth, but you don’t want to say too much.
You keep circling, looking for the perfect line.
And the longer you wait, the more the doubt creeps in.
That was us this morning. We were making a new round of social video tips that were light, playful ideas pulled from our Branding For Beginners book and course. We wanted something to get us out there in a new way. But suddenly, we were second-guessing everything: The framing, the tone, whether our faces looked weird on camera or whether we should just scrap it altogether and try something safer.
So instead of rehearsing, we spun in a chair, we rose into frame from the floor; we made it a little ridiculous on purpose. Not because the content was a joke — but because we needed to break the spell of trying to get it “right.”
And once we did, it felt like us again. Awkward and honest and slightly chaotic… but real. And that’s the only standard we’re trying to meet right now.
That’s the shift we try to make with our clients too — especially the ones who care deeply but keep getting stuck in the process.
If you’re in that place — overthinking the name, the copy, the About page, the next post, the way you describe what you do — what if the answer isn’t a perfect message?
What if you just need a true one?
That’s what our Origin Story Sprint is designed for.
It’s 90 minutes to get what matters out of your head and into a shape that speaks — clearly, calmly, and honestly.
Because the moment your story starts to take shape, the overthinking finally quiets down, and you can start.
