The Plan Paradox
On the necessity and futility of planning ahead
Get your ducks in a row.
Compile your resources.
Scenario plan.
Role play.
Practice.
Then be willing to let it all go
and dance with what is.
Knowing you have prepared as much as you can.
Your plan: That conversation, a figment of imagination. That action, a projection. A movie scene playing out in your mind.
That was then,
and this is now.
We plan to feel ready.
But at some point we need to leave the plan
and walk the high wire without a net.
Sure, we can predict the future,
but with no guarantee of correctness.
Only the future knows.
And it's not telling.
So plan.
But hold the plan lightly.
The future writes itself.
Planning: A Beautiful Contradiction
The tension between preparation and improvisation plays out daily in our lives. We map futures, outline contingencies, and rehearse responses, creating an illusion of control. Yet our most meaningful moments often arise when we loosen our grip (even just a little) and simply respond to what's unfolding before us.
Plans are projects, projections of what may be. A paradox in that we create them expecting them to somehow materialize exactly as envisioned. Except they rarely do.
Even in its multiple definitions, the word "project" contains uncertainty rather than finality:
Noun: a proposed or planned undertaking
Noun: an intention for which something is hoped to be accomplished
Verb: to make a prediction (usually)1 based on known data and observations
Verb: to conceive of or envisage in the mind
In his book, Meditations for Mortals, Oliver Burkeman uses the metaphor of a bridge: we exhaust ourselves worrying about crossing bridges before reaching them, only to discover the actual crossings weren't on our maps at all.2
So do we stop planning then?
No.3 The act of planning is what creates a foundation of confidence, which then allows us to improvise more freely. It's not preparation or improvisation, but rather preparation enabling improvisation.
It's advice I've given clients preparing for anything new: prepare thoroughly, but be ready to abandon the script when the moment demands something different. Advice I often need to give myself.
Whether navigating transitions or simply moving through daily life, perhaps this reflection serves as a gentle reminder: while the map is not the territory, it still helps to bring one along.4
Connecting the Dots
Think about a recent experience where you had to navigate between planning and improvisation. Perhaps it was a work project, a conversation, or even a personal transition.
What did you plan for that actually happened as expected?
What surprised you despite your preparation?
In what ways did your planning help you respond to the unexpected?
Where might you have benefited from holding your plans more lightly?
If you're currently approaching a moment that requires both preparation and flexibility, what's one thing you can do to create a solid foundation while remaining open to what actually unfolds?
The “usually” here my own inclusion as I’ve seen many make projections and predictions and thrust them upon others with no basis in data or factual observations.
This morning's meditation in Oliver Burkeman's book sparked this entire reflection — the starting dot if you will that connected to everything else in this post.
This is wonderful, Maghan. I love what you say about finding preparation enabling improvisation. Yes! I'm a big fan of Burkeman's Meditations for Mortals and have found it so soothing - as is the approach you outline here.