During one of my earlier sailing licences, they gave me an assignment that sounded innocent and, in hindsight, mildly sadistic: prepare a night navigation.
Not “go sailing at night.” Prepare it.
So I did what ambitious, slightly anxious people do when someone hands them responsibility: I over-prepared like it was a competitive sport.
I sat there for hours with charts, bearings, electronics, waypoints, backup routes, contingency routes for the contingency routes. I built this beautiful little cathedral of readiness. Ninety percent of it was… honestly just me trying to feel in control. It looked impressive. It felt mature. It had structure. It had layers. It had that particular smell of “I’m taking this seriously.”
And then I missed something painfully basic: I didn’t properly check whether all the documents and notices were up to date. There was a light that wasn’t there anymore. A tiny detail on paper. A huge detail on water.
So we’re out there in the dark and my neat preparation starts to fall apart. The sea doesn’t care about your scenario tree. And when a light is missing, your entire mental map gets this little crack in it, and suddenly you’re staring at black water thinking: This makes no sense. None of this maps.
I panicked for a moment. Then something shifted. Not because my plan saved me. It didn’t. The plan was now part of the problem.
What saved me was the boring stuff: knowing how to navigate at night on the spot. Understanding what “good enough” looks like when reality refuses to match your imagination. Using what I already knew. Making simple calls. Adjusting. Reading what’s there, not what I expected to be there.
And once I stopped trying to force my prep onto reality, the situation unfolded nicely. Like it often does when you stop arguing with the ocean.
That night comes back to me whenever I see teams drowning in “just in case.”
It’s the same psychology. Different costumes.
Dear Preparedness, please stop trying to be a religion
Preparedness is useful. I’m not anti-prep. I like people who think ahead. I like organizations that don’t improvise everything at the last second. But we’ve turned preparedness into a virtue. Into identity. Into a belief system.
The most admired person in the room is often the one with the biggest risk deck, the most scenarios, the most “coverage,” the most ways to explain why nothing can be decided yet… because responsible leaders prepare, right? Sure. But there’s a difference between preparing as a way to build capability and preparing as a way to manage anxiety.
Psychology actually has definitions for this: proactive coping is not endless thinking. It’s staged and practical: build resources, scan signals, make early moves, learn from feedback.
Prepare → act → learn.
Not prepare → prepare → prepare.
My night nav prep looked like proactive coping. It was mostly emotional management. And it had one fatal feature: it created the illusion that I had handled reality already. Reality loves that illusion. It feeds on it.
Preparedness becomes a problem when it disconnects from action. When it starts producing artifacts instead of decisions. When it becomes a way to avoid being tested.
You can build a career on being “the prepared one” without ever proving you can navigate when the plan breaks. And it will break.
Dear Just-in-Case, you are not a strategy
“Just in case” is a lovely phrase. Sounds responsible like good governance. But “just in case” is also a hidden cost.
It costs time. It costs attention. It costs energy. It costs confidence. Every time you add another precaution, the message underneath is: I don’t believe we can handle this without building a paper fortress first. And the worst part: the organization often looks busy and “fast” while it’s paying that bill. Lots of output. Lots of meetings. Lots of movement.
There’s research on this exact dynamic: people can compensate for interruptions by working faster, but the cost shows up as stress, frustration, time pressure, effort. Speed on the outside. Erosion on the inside. That’s a very modern form of waste… not laziness, but frantic self-inflicted complexity.
My night navigation prep was a just-in-case cost. I paid it with hours. I paid it with attention that should have gone to the basics. And then, out there in the dark, I paid again with a spike of panic because my beautiful plan didn’t fit the world. That’s the thing with costs: you don’t feel them when you’re busy earning. You feel them when you finally look at what’s left.
Dear Uncertainty, I won’t outsource my courage to paper
Most over-preparation is about discomfort. Uncertainty feels like exposure. And paper feels like armor.
Also, and this matters, your brain really doesn’t love doing strategic ambiguity and operational specificity at the same time. Switching between those modes has a measurable cost. Task-switching research has been boringly consistent on this: switching slows you down, increases errors, adds friction, even when you know it’s coming. There’s a burden for reconfiguring your mind.
So yes: people get stuck in planning because execution requires constant context switching and constant micro-decisions in wild reality. Planning is cleaner. Planning is reversible. Planning lets you feel smart without having to be accountable.
At sea, that moment when the missing light broke my mental model… that’s uncertainty in its pure form. For a few seconds, I tried to force my plan onto the world, because that’s what anxious humans do: we argue with reality.
Then, I stopped. I navigated what was actually there. I trusted my competence. It really boils down to building enough anticipation to be ready, while keeping enough self-trust to move when the map is wrong. Because it will be wrong.
Dear Scenario Work, either convert or leave
I like scenario thinking. I’m a fan. Done well, it’s disciplined imagination. It helps you avoid stupid surprises. It gives you a way to practice before you’re under pressure.
But scenario work has a failure mode that looks sophisticated and is, in practice, a form of avoidance: it becomes content. Workshops that produce frameworks that produce decks that produce “alignment” that produces more workshops.
But, anticipation only counts when it converts. If your scenario work doesn’t change a decision, it’s not strategy. Two tools I trust because they force conversion:
Premortem: assume it failed, ask why, fix what’s obvious early. It pulls risk out of polite silence and into concrete design changes.
If–then planning: “If X happens, I do Y.” Not “we’ll consider.” Not “we should discuss.” If X, then Y. Research on implementation intentions is strong for how simple this is: when people pre-decide triggers and responses, follow-through improves reliably. This is the bridge from thought to action.
And it’s what my night navigation prep lacked. I had scenarios. What I didn’t have was the humble discipline of checking the basics and writing the few triggers that matter when things don’t match the chart. You don’t need twenty scenarios. You need three that change behavior. The point remains: convert or leave.
Dear Enough, I trust the crew
Enough is a word people don’t like in ambitious environments. It sounds like settling. Like lowering standards. Like being “not hungry.” Like giving up. But…
- Enough says: we’ve thought ahead, we’ve covered what matters, and now we move.
- Enough says: we will adapt when new information arrives, because we’re not made of paper.
- Enough says: we don’t need to pre-live every disaster to prove we’re serious.
There’s also a cognitive reason “enough” matters: planning can become an illusion of progress. We focus on the plan-based story and underestimate friction, complexity, the fact that real work has a personality. That’s the planning fallacy: we picture the clean version of ourselves executing the clean version of the plan in a clean version of the world.
And then the world shows up. Cloudy. Loud. Dark. Missing a light. “Enough” is where you stop trying to win against uncertainty and start training for it.
So this is my love letter:
Prepare enough to move. Then move enough to learn. Trust competence over paperwork when reality refuses your imagination.
Give anticipation a window. Give execution the longer one.
And build one bridge between them that forces conversion: one premortem, a handful of if–then triggers, one next move. No more.
Because you do care. The goal was never to be prepared for everything. The goal was to be prepared enough… and skilled enough to navigate what you didn’t prepare for.