Commit to the tack
tl;dr: Everyone talks about pivoting. Sailing has a better word for what good decision makers actually do: tacking. Same destination, different route, because the conditions demand it.
We are all sailors
Long before we had written language, formal governments, or anything resembling a corporation, we had boats. Sailing is the foundational human experience of venturing into uncertainty with a plan, a crew, and limited resources. Every problem you face running a company has an analogue on the water.
Consider how deeply sailing is already embedded in how we talk about work. Getting someone "on board" meant literally stepping onto the vessel. "Weathering a storm" is borrowed from crews who survived heavy seas without sinking. "All hands on deck" was the original escalation protocol: every crew member needed topside, immediately. And "dead reckoning" is estimating your position based on your last known location, speed, and heading. No external data. Just internal momentum and assumptions.
We did not borrow these phrases for decoration. We borrowed them because the situations they describe are universal. The sea was the first environment where humans had to make high-stakes decisions with incomplete information, limited resources, and a team that needed to execute under pressure. Business is the second.
Tacking: the decision that matters most
You want to go north. The wind is blowing from the north. You cannot sail directly into the wind. So you tack. You sail northeast for a while, then turn and sail northwest. Then northeast again. You zigzag your way upwind, making progress toward your destination without ever pointing straight at it.
Tacking is the most underappreciated business metaphor I know. It captures something that "pivot" does not. A pivot implies you were wrong and are now going a different direction. A tack implies the destination has not changed, but the conditions require an indirect approach. You are still headed north. You are just getting there in a way that works with the forces acting on you, not against them.
Every tack is a decision point. When do you turn? Too early and you waste distance. Too late and you lose ground to leeward. Each tack costs you time and energy (the crew has to move, the sails have to be reset, the boat slows during the turn). So you want to minimize tacks while maximizing the ground gained on each one.
This is iterative decision-making. Sense the conditions, commit to a direction, execute, monitor, and know when to turn again. Overcorrecting (tacking too often) is just as costly as being stubborn (refusing to tack when the wind demands it).
Consider a concrete example. Warby Parker's destination was clear from the start: make quality eyewear affordable and accessible. They launched online-only, betting that people would buy glasses without trying them on. But the conditions told a different story. Customers loved the product, but many still wanted to try frames in person. Online-only was leaving real growth on the table. So Warby Parker tacked. They opened retail stores. Not because the vision changed, but because the route needed to. Same destination, different approach, driven by what the market was actually telling them.
Reading the conditions
You cannot control the wind. You cannot control the tide. You cannot control the weather. You can only observe, anticipate, and respond.
This is the hardest lesson for new sailors and new leaders alike. There is a strong human instinct to believe that with enough planning and effort, you can control outcomes. The ocean disabuses you of this quickly. You can do everything right and still get hit by a storm. You can make a poor decision and get lucky with a favorable current.
On the water, the consequences are not abstract. A wrong call in a rising storm does not mean a missed quarter or a difficult board meeting. It means the boat on the rocks. Crew in the water. When the cost of a bad decision is survival, you develop a different relationship with risk. You respect the conditions more. You prepare more honestly. You listen to the crew member who says something feels wrong. Most business decisions are not life or death. But the organizations that treat their environment with the same respect, that genuinely believe conditions can overwhelm a plan, make better calls than the ones running on confidence alone.
Experienced sailors develop a feel for reading conditions. They watch the sky, the water surface, the barometric pressure. They build an intuition for what is coming before the instruments confirm it. The best business leaders I have worked with do the same thing. They sense shifts in the market, in team morale, in customer behavior, before the data shows it clearly. That intuition is not magic. It is pattern recognition built from paying attention over a long time.
The thing with a charted course, it is wrong before you leave the dock. The chart shows you the plan. The sea shows you the reality. Wind shifts, currents change, a storm system moves faster than forecast. The best navigators hold the plan loosely and adapt constantly. They check their position frequently, compare it to the plan, and adjust. They do not fall in love with the original route just because they drew it.
What the water taught me about decisions
I want to close with three things sailing has taught me about making decisions, in business and everywhere else.
Slow down. You have more time than you think. When something goes wrong on a boat, the instinct is to react immediately. But in most situations, you have more time to assess and respond than you think. A sail starts to luff. The boat heels more than expected. A line jams. The first thing you learn is to pause, breathe, and look around before you act. Panicked reactions on a boat cause more damage than the original problem. The same is true in business. The decision you rush is almost always worse than the decision you take ten minutes to think through.
Pay attention to the forces, not just the destination. The boat does not care about your plan. The wind does not care about your deadline. You can fight the conditions or you can read them and adapt. The sailors who spend the most time looking at the water, feeling the wind, and watching the sky are the ones who make the best decisions. In business, the leaders who spend the most time with customers, watching the market, and sensing the environment are the ones who navigate best. Good decisions come from good inputs, and the best inputs come from paying attention to the world around you, not staring at the chart.
Commit to the tack, not the course. The destination matters. But the path to get there will change. The best decision makers I have seen, on the water and in the boardroom, share the same quality: they commit fully to their current heading, execute with focus, and then reassess without ego when conditions shift. They do not tack every five minutes out of anxiety. They do not hold a bad course out of pride. They make the best call they can with the information they have, they act on it, and they stay ready to turn.
A skilled sailor was never made by planning alone. They were made by reading the conditions, choosing a tack, and having the judgment to know when it was time to turn. The best leaders I have worked with were made the same way.