Making Rules Matter

Making Rules Matter

Sensibility Follows Structure

Chris Cowan's avatar
Chris Cowan
Jun 05, 2026
∙ Paid
“There is a quality even meaner than outright ugliness or disorder, and this meaner quality is the dishonest mask of pretended order, achieved by ignoring or suppressing the real order that is struggling to exist and to be served.” -Jane Jacobs (1961)

In most organizations, it’s very difficult to change things. People sometimes dream about leadership positions simply because it seems like that is the only way to impact how things get done.

You bring up the bottleneck in your weekly one-on-one. Nothing happens. You raise it at the team meeting. Nothing happens. You write a careful email about it. Maybe you get a polite reply, maybe not. Either way—nothing really changes.

After a while, you stop bringing it up. But something else happens too. You don’t just stop raising the issue—you stop feeling it.

It’s a good strategy. If you can’t change something, why make yourself miserable worrying about it? So, you adapt. You get good at not noticing.

The bottleneck becomes “just how things are.” The colleague’s behavior becomes “his thing.” The way meetings run becomes “the culture.”

If your feedback goes nowhere, what’s the point of feeling strongly about it? Numbness is the better option.

I think this is part of why adopting a practice like Holacracy is often harder than it looks—and harder in ways that don’t get talked about.

People start practicing it, and a wave of tensions surfaces. Some are about Holacracy itself, of course. But a lot of them aren’t.

User's avatar

Continue reading this post for free, courtesy of Chris Cowan.

Or purchase a paid subscription.
© 2026 Chris Cowan · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture