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CHAPTER 1

WHY SUCCESS CREATES RIGIDITY.

Organizations don't fail because they stop doing what made them successful. They fail because they can't stop.

I had a great football game once. High school. Group home kid. Foster care system.

I played out of my mind. We won. Everyone went home.

I sat on the steps outside the stadium, alone, watching my teammates drive off with their families. Watching the lights go out.

Success isn't what you think it is. Success is what you optimize for. And what you optimize for becomes what traps you.

THE GOODWILL PROBLEM

2005. I was a GIS analyst. Goodwill wanted to enter urban Chicago. My team identified nine precision locations with demographic support and growth trajectories.

They tested one. Madison and Halsted. It worked. Still one of their best-performing stores.

Then they stopped.

One store. Out of nine. With a model that could scale nationally.

"It may have been too good. Pissed some people off."

My boss, when I asked what happened

Goodwill had been successful for decades. That success had become infrastructure.

Careers built on the old approach. Budgets justified by existing process. A real estate team whose judgment we'd just replaced with data.

Optimization creates dependency. Dependency creates defenders. Defenders become particles.

19

years to do what the data said in 2005

Goodwill opened in Avondale in 2024. One of our nine locations.

FIELD SYSTEMS

Information flows freely. Decisions happen where knowledge is. Energy passes through without getting stuck.

PARTICLE SYSTEMS

Departments bounce off each other. Information gets trapped. Every handoff loses energy to friction.

Success creates mass. Mass creates gravity. Gravity pulls everything into fixed orbits.

"Good management was the most powerful reason they failed."

Clayton Christensen, The Innovator's Dilemma

Tesla built the EV revolution. BYD is winning it.

In 2025, BYD passed Tesla in global sales. Not because Tesla failed. Because Tesla succeeded so thoroughly the success calcified.

Same two car models drive 95% of volume. Same founder-centric decisions that enabled rapid innovation now create bottlenecks.

Tesla isn't dying. It's calcifying.

THE ERA SHIFT

1995-2025: Connection Era. Success meant who you knew. What networks you belonged to. How much access you had.

2025+: Coordination Era. Everyone's connected now. The moat became the ocean. What's scarce is the ability to move together.

When Slack went down for a few hours, productivity went up 5%.

52%

Fortune 500 from 2000 are gone

70%

Digital transformations fail

THE PATTERN EVERYWHERE

Healthcare: Prior authorization delays care for 93% of physicians. 82% of denials get overturned on appeal. The system pays anyway, four out of five times.

Enterprise software: Average large company has 371 applications. Half unused. Try to consolidate. Watch the implementation partners, integration vendors, and internal teams fight back.

Every successful solution became someone's job. Every job became identity. Every identity became a particle defending its position.

"The illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn, and relearn."

Alvin Toffler

The question isn't "how do I fix my organization."

Most can't be fixed from inside. Particles too defended. Mass too great.

The question is: what do you do with this knowledge?

That kid on the stadium steps didn't fail. He succeeded at the wrong game.

Your organization is that kid.

Built for connection when connection was hard. Successful at everything that mattered in 1995, 2005, maybe 2015.

The game changed. The infrastructure didn't.

The dysfunction is the success. You're drowning in it.

From the upcoming book

The Growing Pains Index

Chapter 1: Why Success Creates Rigidity

MEASURE YOUR RIGIDITY

32 questions. See where success became constraint.

TAKE THE DIAGNOSTIC