The Best Plan Is Not the Best

Editor’s Note: This essay sits within Cultivated’s broader inquiry into clarity, momentum, and the cost of organisational overthinking. It reflects on planning as a thinking tool rather than a bureaucratic artefact.

The Best Plan Is Not the Best

If you have read my work or worked with me, you will know this:
I care about planning.

But I do not care about plans.

Planning sharpens the mind. It creates perspective, forces trade-offs into the open, and invites creative problem solving.

The act of planning is thinking made visible.

The artefact that emerges
— the plan
— is something else entirely.

Planning attracts a particular cast of characters.

Detail lovers.
Risk mitigators.
Perfectionists.
Committees seeking safety.

The plan becomes insurance. A shield. Something to defend.

The logic quietly shifts.

If the work does not go well, perhaps the plan was not good enough. So we plan more. We refine. We seek alignment. We chase consensus.

We search for the “best” plan.

What does best mean, anyway?

It depends who is in the room, what incentives are in play, and how anxious everyone feels that day.

Meanwhile, time, energy and attention drain away in debates about the intelligence of the plan rather than experiments and action and tactics in reality.

The customer does not care whether the plan was immaculate.
They care whether something useful exists.

All plans are wrong.

Few survive contact with markets, people, and organisational complexity.

The world moves, constraints shift, people reinterpret, and reality diverges from the spreadsheet.

Effective leaders understand this.
They use planning to think, to surface risks, to align intent, and to take the first step.

Then they adapt.
They revise.
They discard.
The plan is a starting hypothesis, not a contract with the future.

Ineffective leaders cling to the plan.

Deviation becomes a transgression.
Following the plan becomes the only goal.

The work becomes window dressing in service of a document that was out of date the moment it was approved.

Harry Beckwith (aff link) in Selling the Invisible, ranked plans this way:

very good,
good,
best,
not good,
truly awful.

In chasing “best”, organisations stall. They avoid action. They treat imperfection as a moral failure rather than the only viable path to learning.

No plan is chaos.
Planning is clarity.

But the pursuit of the best plan is often organisational window dressing
— expensive, slow, and detached from value creation.

Businesses exist to serve society by delivering something worth paying for.
Revenue follows.

Value requires action.
Action requires movement.

A very good plan is usually enough.

Because the only way to know whether a plan works is to put it into the world, let reality respond, and learn.