Practical Philosophy of Systems

Last time we explored how incentives quietly reward shortcuts over substance and why capable people end up simulating value instead of creating it.

This month, we're tackling the next layer: How do you scale a group (whether a team, community, company, or even a friend circle), without losing the speed, closeness, and spirit that made it great when small?

Small groups move fast. Decisions are quick. Everyone knows the context. Then growth happens, and suddenly, more coordination, more rules to stay aligned, people drifting away because "it's not what it used to be."
The pattern shows up everywhere: startups, communities, families, friend groups, open source projects, and social movements. Growth naturally breeds bureaucracy and rigidity. More people mean more alignment. More alignment needs coordination. Coordination requires process. Process becomes overhead. The edge dulls. But some systems scale without this decay. They grow capacity while preserving speed. Why?

The questions we're exploring:

• Why does growth naturally produce bureaucracy and rigidity—and what are the rare exceptions doing differently?
• How do you preserve the speed and culture that made a system work when it was small?
• What causes people to stay engaged as groups mature, instead of quietly checking out or drifting away?

This isn't about resisting growth or romanticising smallness. It's about understanding why bureaucracy and rigidity emerge as natural byproducts of scale in any human system, so we can design structures (in our work, our communities, our relationships) that work against that gravity.

Please keep your RSVP current.