The Crooked House Problem: When Stability Stops Progress
I Solved a 400-Year-Old Problem on Vacation
Somewhere between sightseeing, eating far too well, and convincing myself that walking all day justified dessert, I solved a 400-year-old engineering problem. Historians, architects, and preservationists may want to sit down.
Why didn’t anyone think to just push it sooner?
Jokes aside, the moment came while standing in front of the Crooked House of Canterbury, a building constructed in 1617. It has survived plagues, wars, monarchs, industrial revolutions, and more architectural trends than anyone cares to count. It has also become famous for one very specific reason. It leans.
Not dramatically. Not alarmingly. Just enough that you notice it immediately and cannot unsee it once you do. That lean is not an accident. It is the result of centuries of gradual settling on uneven ground. Gravity did what gravity always does. Slowly, patiently, and without any concern for human plans or timelines. The house did not fail. It adapted. And that adaptation holds a far more useful lesson than any perfectly straight building ever could.
Gravity, Foundations, and the Illusion of Stability
The Crooked House did not wake up one morning and decide to become crooked. There was no catastrophic event and no single bad decision. The timber frame settled little by little. Floors sloped. Walls bowed. Doors began to open themselves if you were not paying attention.
This is how most real problems emerge. They arrive quietly. They compound slowly. They stay just within acceptable tolerances long enough for people to normalize them.
From an engineering standpoint, the house could be straightened. The methods exist. The math works. But the cost would be enormous. Large portions of the structure would need to be dismantled. The foundation would have to be rebuilt. Modern materials would be introduced. In the process, the building would risk losing the very thing that makes it valuable. Straightening it would almost certainly erase its character.
So the decision was not to fix it in the conventional sense. The decision was to stabilize it. Reinforcement was added. Careful, ongoing maintenance became non-negotiable. External supports ensure that the lean does not turn into collapse. The objective was not perfection. The objective was preservation. And that decision was entirely rational. The key detail is why it was rational.
When Stabilization Is Alignment and When It Is a Trap
The Crooked House still exists because its purpose was preservation.
The goal was not growth. It was not efficiency. It was not scalability. It was to protect what already existed, even if that meant accepting constraints and imperfections. In this context, the lean stopped being a flaw and became the value. The crookedness is the story. People do not visit despite it. They visit because of it.
Stabilization worked because it matched the intent. This is where the metaphor becomes uncomfortable for business leaders.
Most organizations are not trying to preserve a historical artifact. They are trying to grow, adapt, scale, and compete in environments that change constantly. Markets shift. Technologies evolve. Customer expectations rise. Talent moves faster than org charts. Yet many organizations respond to these pressures by doing exactly what the Crooked House did, without understanding why it worked there and why it may not work for them.
They reinforce systems that were never designed for today’s demands. They add layers of process to compensate for misalignment. They introduce tools, integrations, roles, and reviews to keep things standing. In practice, this usually looks like:
People manually compensating for system limitations
Workarounds that were supposed to be temporary becoming permanent
Growing complexity introduced to preserve the appearance of stability
More coordination required to achieve the same outcomes
Progress feeling harder every year instead of easier
None of this happens because leaders are careless. It happens because stabilization feels responsible. It feels safer than admitting that the foundation itself may no longer fit where the organization is trying to go. But survival and progress are not the same thing.
Straighten It or Rethink It Entirely
Rebuilding foundations is disruptive. It introduces short-term pain. It forces trade-offs. It exposes assumptions that have been comfortably hidden for years. That discomfort is precisely why organizations avoid it.
But avoiding foundational change does not eliminate cost. It simply changes how the cost shows up.
Instead of paying once to realign the structure, organizations pay continuously through inefficiency, frustration, attrition, and missed opportunity. They pay when talented people spend their time managing friction instead of creating value. They pay when leaders make decisions with incomplete information. They pay as agility slowly leaks out of the organization. Gravity remains patient. Complexity compounds quietly.
The Crooked House of Canterbury is not a warning about failure. It is a lesson in alignment. The reason it still stands is not because it was fixed, but because the solution matched the purpose. That is the question most organizations avoid. Before adding another support beam, another tool, another role, or another workaround, it is worth asking a harder question.
Is this something we are preserving intentionally, or something we are protecting out of habit?
If the goal is preservation, stabilization can be a disciplined strategy. If the goal is growth, propping up a misaligned foundation is often the most expensive way to stand still. Straightening is expensive. Pretending you do not need to is expensive too. Only one of those choices actually builds a future.
