Why Smooth Sailing is the Riskiest
When the ride is the most gentle is when the boom swings
“The voyage of the best ship is a zigzag line of a hundred tacks. See the line from a sufficient distance, and it straightens itself to the average tendency. Your genuine action will explain itself, and will explain your other genuine actions. Your conformity explains nothing. Act singly, and what you have already done singly will justify you now.” ― Ralph Waldo Emerson, Self-Reliance
The most comfortable and the most peaceful moment when out sailing is when the wind is at your back. The same is true in life, and hence the saying, “May the wind be always at your back.” This also happens to be the most dangerous point of the journey, because if you lose sight of your destination for even a few minutes, the winds may shift. Or if your instrumentation is miscalibrated even to the slightest degree, you might quickly and unknowingly veer in the wrong direction.
When sailing with the wind at our backs, we don’t feel its full force. It’s as if there’s no wind at all. The other risk of heading straight downwind is demasting due to an accidental jibe. This happens when the boom swings violently and quickly from one side of the boat to the other. It can be so sudden and so violent that demasting (i.e., losing the mast entirely) can capsize the boat.
The danger of becoming comfortable in conditions of smooth sailing can be much riskier than setting off in troubled waters. Because at least in stormy weather, we’re more accurately attuned to the risks involved. So in sailing—as well as in our personal and professional lives more broadly—when the wind is at our backs and we are most comfortable, it is then that we’re exposed to the highest relative risk. When the ride is the most gentle is when the boom swings and smacks us full on the head.
What I mean by applying this sailing metaphor to business is that although we have learned to see comfort in our professional lives as a positive, it is at those times that we must be the most careful and aware of our surroundings. Being attuned holds the key to deep relaxation, knowing that I’m keenly aware of my environment, and not taking anything for granted.
Practically speaking, the way that I stay on course is to “stay hungry” and root out complacency. We’re either growing or dying; that’s how nature works. I find that when I’m no longer hungry for success, that is a sign that I’m not growing. I choose to look at this in terms of what I call “bigger arcs and little dots.”
The bigger arcs include making bold career moves that were actually the safest and most optimized, risk-adjusted move I could have chosen. These types of risks continue to pay remarkable dividends, as I am now contributing and being rewarded for my talents as the West Coast General Manager for Hunt Club, an innovative, tech-enabled recruiting firm.
The “dots” I referred to earlier are the daily routines I practice in my own life. For me, ritualizing regular mediation, exercise, a healthy diet, and learning are all expressions of staying aware and being careful, and they help me keep the “wind in my sails.”
What are your practices for sustaining the wind at your back? And how can you tack and leverage the zigzags to achieve your objectives?