Prison or Asset?
Do you own a business — or does your business own you? 10 questions, honest answers.
The Two Kinds of Companies
There are businesses that imprison their founders, and businesses that serve them. The difference is structural, not financial.
Most entrepreneurs do not realize they are running a prison company until something breaks — a marriage, a body, a business, a soul. By then, the cost of escape is high.
This 10-question diagnostic measures the structural health of your business across the dimensions that matter: founder dependency, process documentation, leadership depth, financial reserves, and decision distribution.
Each question is rated from 1 (Strong Prison) to 10 (Strong Asset).
1. My business can operate without me for one full week without crisis.
2. Major decisions are made by appropriate level — not all routed to me.
3. Revenue does not depend on my personal effort or relationships.
4. The team functions normally in my absence with maintained standards.
5. All essential processes (sales, delivery, service, finance, hiring) are documented.
6. I can take real vacation without working remotely or being constantly available.
7. Team members can solve problems at their level without escalating to me.
8. I have built a leadership team with active development plans for each person.
9. We maintain at least 3 months of operating expenses in cash reserves at all times.
10. I focus most of my time on Vision, Culture, Leaders, and Critical Decisions — not operational work.
Answer all 10 questions.