Jason Fried wrote1 that the main benefit of being an entrepreneur is that “You get to do things no one would give you permission to do.”
This idea of permissionless work always spoke to me on a fundamental level, but it felt vague. It felt like a luxury I might have in the future, but not now. When I started to work in earnest on my new company this year, I hoped to attain it. Still, it wasn’t until last week that I experienced a concrete manifestation of that freedom.
I created a short video clip that demos the upload feature, and I needed some mock files and descriptions to display in the upload form. I spent some time searching for something sensible and sifted through test files, but everything was either cryptic or boring. I became frustrated and felt trapped doing a marketing task that I felt unqualified for. And then it struck me: I can just create something that I find amusing!
So now I use our upload form to poke fun at the crypto hype and the “waking up early” fetish. And I got to use a picture of my dog. For the second form, I used a shower thought about oceans being roads that don’t require maintenance.
And as I created the clip and integrated it into the page, I felt unburdened, enjoying the absurdity of doing something silly at work. I felt aligned with what I think I should do more often: Do things for the fun of it.
I believe it’s an excellent strategy for an early-stage startup to lean into this feeling of permissionless freedom. It creates an emotional connection with early customers, which might make them ignore some rough edges. And since we won’t be able to please everybody, we should double down on customers that like our style. We might need to soften our voice as we grow, but we’ll see. It would be an excellent problem to have.
There’s obviously a limit to this freedom. If too many customers tell me they hate the clip, I’ll probably change it. But the fact that I got to try without asking for permission fills me with joy.
If you’re interested in how this plays out and the occasional shower thought, you can follow me on Twitter🦜.