Plans Are Maps, Not Territory
Plans guide action, but reality changes. Why plans must be living maps that evolve through learning in Releasing Agility.
Editor’s note: This essay sits within the Cultivated library on systems, learning, and organisational navigation. Plans are explored as maps that bridge narrative futures and execution — instruments for learning, not instructions to follow blindly.
The Trouble With Plans
I have a complicated relationship with plans.
I love them.
They bring clarity, align people, and help us ignore the thousand small problems that distract from what matters.
I dislike them.
Too often, plans become dogma. Following the plan becomes the goal. The value the plan was meant to achieve quietly disappears.
The Map Is Not the Territory
Alfred Korzybski captured this perfectly:
The map is not the territory.
A plan is a map.
Reality is the terrain.
Maps are abstractions. They simplify, compress, and distort reality so we can navigate. They are essential — and always wrong in detail.
Plans in Releasing Agility
When Releasing Business Agility, planning sits after sensemaking.
First, we paint a picture of the future.
Then we understand why we are not already there.
Only then do we design the plan.
Plans bridge the gap between narrative intent and operational reality.
They are the first translation of meaning into action.
Why Plans Go Out of Date
A good plan becomes obsolete quickly.
If it doesn’t, something is wrong.
Markets shift. People leave. Constraints appear. Knowledge changes. Problems are resolved, or created.
If your plan survives untouched, you are likely not learning, not stretching, and not moving.
The plan is still valuable.
But it must evolve with the terrain.
What a Good Plan Must Do
A plan should do three things:
Give direction.
It should show the path from now to your painted picture.
Create space for learning.
Reality will reveal new constraints and opportunities. A plan must bend without breaking.
Anticipate mistakes.
Failure is information. Plans must assume error, experimentation, and recovery.
Tiny Forces, Big Drift
Every decision, interaction, and misstep exerts force on your system.
Small deviations accumulate.
Follow the map without noticing the terrain and you drift quietly off course.
Plans must be revisited, not revered.
Learning Is Essential
A plan does not create learning.
Execution does.
Tactics generate information. Feedback loops reveal what works and what doesn’t. Learning updates the map.
It is the mechanism that releases movement.
Plans as Alignment Instruments
Plans align people.
They communicate intent, priorities, and constraints.
No plan creates confusion.
A rigid plan creates stagnation.
A good plan is a living artefact — reflective, adaptive, and revised in the light of learning.
No Plan Survives Reality
The military adage is right:
No plan survives first contact with reality.
This is not an argument against planning.
It is an argument for adaptive planning.
Plan. Learn. Adapt. Repeat.
Plans are maps, not commands.
Learning is the compass.
Reality is the terrain.
Create a plan.
Use it.
Learn from it.
Change it.
That is how you release agility.
This piece forms part of Cultivated’s wider body of work on how ideas become valuable, and how better work is built.
To explore further:
→ Library — a curated collection of long-form essays
→ Ideas — developing thoughts and shorter writing
→ Learn — practical guides and tools from across the work
→ Work with us — thoughtful partnership for teams and organisations
