People who have never sailed think a sailboat only works when the wind pushes from behind.
It's not so.
At sea, the wind almost always comes from where you'd rather it didn't: head-on, against the course you have in mind. And that's where the thing happens that looks like magic from shore: the boat manages to go toward the wind. Not straight into it — that's impossible — but in a zigzag, angling the course first one way, then the other.
It's called tacking: pointing as close to the wind as you can, sailing one leg, then coming about and sailing the opposite leg. A broken line that, seen from afar, takes you exactly where you wanted to go.
The novice sailor, when the wind turns against them, gets scared. The experienced one doesn't.
Not because the sea has turned gentle. Because they know one thing: a headwind is not something you endure, it's something you work.
And the first thing they do, before even touching the helm, is not look at the wind.
It's look at where they are.
The unexpected always arrives head-on
In personal finance, the headwind has three recurring faces.
The big, sudden expense: the car that breaks down, the roof that gives way, a treatment that can't wait, a tooth that costs as much as a vacation.
The income drop: a client who bails, a contract that isn't renewed, reduced hours, and for freelancers a quarter that's simply empty.
The market down: you open your investments summary and the number is smaller than a month ago. Sometimes much smaller.
Three different winds, one and the same gut reaction: the stomach tightens.
And almost always, in that moment, the wrong maneuvers begin.
Someone sells an investment on the worst possible day to "get safe". Someone signs the first loan that comes along, at the first terms that come along. Someone takes a job they don't want, in a rush, because fear of next month dictates the answer.
They're all moves made blind. Moves by someone watching the wind and forgetting to watch the boat.
There's a different way. It doesn't eliminate the wind — nobody eliminates that. But it turns panic into a maneuver.
Calm doesn't come from the absence of waves
Let's get one thing clear, because it's the heart of it all.
The serenity Cashfulness talks about is not the illusion that the unexpected won't come.
It comes. Always. To you, to me, to the best skipper in the harbor.
The experienced navigator's calm doesn't come from a flat sea. It comes from knowing, at every instant, where their boat is. That coordinate tells them whether there's water under the keel, how much margin they have, which maneuvers they can afford and which they can't.
In personal finance that coordinate has a name. I call it the position fix: everything you own minus everything you owe, your exact position at this instant. (I've written about it here, if you want the foundations.)
And next to the position fix there's a second reading, the one that matters more than any other when the unexpected hits: your months of coverage. How many months of your life you can pay for with the liquid money you have today, if your income stops tomorrow. (Here at length.)
Two numbers. Where you are, and how long you can hold.
Whoever has them in view, when the wind turns, doesn't improvise. They tack.
What changes with a number in place of fear
Let's take the most frequent example, the big expense.
Marco's car breaks down. The mechanic is clear: either €3,200 of repairs, or replace it. A headwind, dead-on.
Marco without a position fix lives the scene like this. He opens his banking app, sees the account balance — say €4,800 — and panics. If I pay, I'm left with almost nothing. His head spins off: do I sell something? Ask for a loan? Put it off and walk in the meantime?
He decides under stress, from the gut. Almost always badly.
Marco with the position fix lives the same scene differently.
He looks at the coordinate, not just the account. He knows his net worth, everything included, is €41,000. He knows his months of coverage stand at 5: even paying the €3,200 in one go, he keeps a little over 4 months of full autonomy.
The expense hurts just the same — €3,200 is still €3,200.
But it's no longer a catastrophe. It's a maneuver inside a margin Marco knows.
He sees he can pay with liquid funds without touching his investments, without loans, without selling anything at a loss. Coverage drops from 5 months to a little over 4: below the comfort threshold he set for himself, but still inside a margin that holds. He already knows what the following weeks' work is: slowly rebuilding the half month of coverage he consumed.
Same wave. Opposite reaction.
The number didn't remove the expense. It removed the panic around the expense. And without panic, Marco chose well.
This is tacking: the wind is still there, but you know exactly how close you can point.
Three tacks, one for each wind
Tacking means choosing your tack — the side you take the wind on — based on where you are. Each kind of unexpected has its right maneuver. Let's look at them one by one, always starting from the coordinate.
Wind 1 — The big expense
The question is not "do I have the money in the account?". It's "how many months of coverage does this expense cost me, and where does it leave me?".
Three cases.
If after paying you stay above your comfort threshold — say three months for someone with a stable income — you pay with liquid funds and file the matter away. This is exactly what the coverage existed for.
If the expense takes you below threshold but not to zero, you still pay with liquid funds, but you put the rebuilding work on your agenda. That's Marco's case.
If the expense wipes you out or nearly, then the decision widens: maybe you pay in installments, maybe you do only the indispensable part now. But it's a choice made looking at the chart, not with your stomach.
The rule beneath all three cases: liquid first, before the loan, before selling an investment. You draw from where it does the least damage.
Wind 2 — The income drop
Here, months of coverage stop being a statistic and become an operational compass.
If the wind is your income dropping, coverage tells you how much time you have to maneuver before you're forced into emergency decisions.
Five months of coverage means five months to find a new client, a new contract, a new path — without having to accept the first thing that floats by just to stay above water.
Time, in the face of an income drop, is the scarcest resource. And months of coverage are exactly that: time bought in advance. Time to say no to a bad offer. Time to wait for the right one.
Without coverage, facing an income drop, you don't tack: you get pushed wherever the wind takes you. With it, you choose the course.
Wind 3 — The market down
This is the wind that scares the most and that, almost always, calls for no maneuver at all.
A falling market makes your net worth fall. You see it, on the position fix, and it's unpleasant.
But there's a distinction that changes everything. That money is not coverage — coverage is made only of liquid funds, of what you can use within 24 hours without selling anything. Investments are something else: they're the part of your wealth that works over the long run.
A market drop touches the big number, your net worth. It doesn't touch the months you can hold.
And so, in the vast majority of cases, the correct maneuver is no maneuver. Selling during a decline means turning a paper loss into a real one. It's the sailor who, seeing the wave, jumps off the boat.
Here the position fix does its most precious work precisely by not pushing you to do anything. It shows you the drop, shows you your coverage is intact, and lets you breathe until the wind turns again — because it always turns.
The only real precaution is taken beforehand, in calm seas: keeping your coverage in liquid funds and not among your investments, so that when the market falls you're never forced to sell at the worst moment.
The advantage is built in fair weather
There's an uncomfortable truth in all this.
The maneuver against the unexpected is not learned during the unexpected.
The experienced sailor knows how to tack because they've taken their position fix a thousand times on a flat sea, when it served no urgent purpose. So when the wind turns, the gesture is already automatic: look at the position, then decide.
It's exactly the same with money. If the first time you look for your position fix is the evening the car broke down, you look for it in a panic — and that's the worst moment.
That's why Cashfulness insists so much on the small, repeated gesture: ten minutes, every now and then, looking at your coordinate when nothing is happening. Almost always there's nothing to do. That's precisely the point.
You're training the reflex. So that, the day the wind truly turns, your first reaction isn't your stomach tightening.
It's your eye going to the chart.
Knowing where you are doesn't stop the wind
I'll come back to where I started, because it's what I care about most.
The position fix doesn't promise calm seas. No honest tool promises that, and beware of any that does.
The unexpected will keep arriving head-on, as it always has. The big expense, the client who bails, the falling market: they're part of sailing, not a defect of the system.
What changes is how you cross them.
Without a coordinate, every headwind is a small crisis: you decide in the dark, in a rush, and often end up where you didn't want to be.
With the coordinate, the same wind becomes a maneuver. You know where you are, you know how long you can hold, you know what you can move without doing damage. Fear gives way to a practical question: what's the right tack, now?
Money is a tool for buying time and freedom — not a dream to chase, nor an enemy to fight. And in the face of the unexpected, freedom has a very concrete shape: being able to choose the maneuver instead of enduring the wave.
Cashfulness doesn't stop the wind.
It gives you the position to tack from. The rest — when to come about, how close to point, where to go — is a choice that remains yours. You make it informed.
— Vittorio