O Captain! my Captain! our fearful trip is done,
The ship has weather’d every rack, the prize we sought is won,
The port is near, the bells I hear, the people all exulting,
While follow eyes the steady keel, the vessel grim and daring;
- Walt Whitman, Leaves of Grass
I’ve just returned yesterday from a 7-day sailing adventure vacation in Croatia, zig-zagging through several islands on the Dalmatian Coast.
After spending a week on the chartered sailboat with our skipper, it was hard to miss the similarities between his job and mine as a startup CEO.
Charting a course
The first role of a skipper is to chart a course. The course must be ambitious and exciting enough to convince a band of men to forego the comforts of land to join his adventure. The course must also be realistic enough that the band of men have a meaningful chance of reaching the destination of this adventure within a given period of time. This course is his vision. “If one does not know to which port one is sailing, no wind is favourable”, Roman philosopher Seneca once mused.
That said, only some skippers will have the luxury of knowing their port of arrival. Others, like great explorers Columbus, Vespucci, Magellan, Hudson, Cartier and Champlain, will sail with more uncertainty and risk in the hope of making a major discovery.
Once the course is set, the skipper devises an actionable itinerary. His role will be to navigate his boat and to lead his crew to the promised land. At any given point in the journey, he is charting progress against his plan. He has one hand on the wheel and one eye on the horizon. He is always ready to adjust the direction of his sailboat five degrees to the left or right if needed. The course, he will find, is quite dynamic. Storms, pirates, boat failures and other unforeseen obstacles will unfailingly appear and stand in his way, as they did in Homer’s Odyssey to its hero Odysseus on his epic sailing journey home.
A strong stomach
A key requirement for the skipper is to have a strong stomach. First, there is the courage to leave. Oceans can never be crossed without the courage to lose sight of shore. Furthermore, sailing the often turbulent seas is not for the faint of heart. The skipper is driven by his need to discover the secrets of the sea. The joy of the open sea is everything. For him, this outweighs the personal risks of getting swallowed by the power of the sea, or worse even, the danger of drifting off course into irrelevance.
There are different varieties of skippers. The smaller the boat, the stronger the stomach typically.
First, there are the skippers of small sailboats. These are the startup CEOs. The boat initially has only one or two places, but will eventually be upgraded to hold a small crew. The boat initially has only a small sail, but will eventually be upgraded to larger and higher performance sails as their finances improve. The boat is powerful, often more so than the skipper’s capacities to harness its power, but not exactly fine-tuned. The crew onboard are generally novice. On this journey, the skipper and crew will learn together. The goal is agility, then later power. The adventure quotient is high.
Then, there are skippers racing sailboats. The racers also care about journey, but the big difference is that they especially care about time. In a way, they are like the CEOs of venture-backed startups. They race against the watch.
Finally, there are professional skippers. They race large yachts with expert crews and often infinite resources to win. These are the professional CEOs of large companies. They typically sail courses that they have not themselves charted. While the name of the job is the same, the quest and adventure could not be more different.
Master of the ship
The skipper must know his boat inside and out. Every line and every nut and bolt. The skipper must know everything and be prepared for every eventuality, even if everyone knows that this is an impossible standard.
When a piece unexpectedly fell from the main sail during our trip, our skipper took control of the situation, methodically lowered the sails and proceeded to making the repair on the spot. There is often no time for a manual when one is at sea. The skipper must know what to do. In any case, he must act.
The skipper must command his crew. He must be a clear communicator. Timing is critical when sailing. A split-second can make the difference between a successful or a botched maneuver. Teamwork is necessary to navigate efficiently. The skipper must motivate, orchestrate and delegate. His crew must implicitly trust his authority. At some point, the crew will come to run the ship, not the skipper. That will be a good thing.
He must also lead the celebration in good times. He cracks open the bottle of wine with his crew when the time is right. He must also be the disciplinary force in bad times. He sleeps with one eye open. When one of his crew fails to return to the vessel in the wee hours of the night, after too much wine in the port, he takes the zodiac to bring him back to ship.
With the years, the skipper gains in skill and experience. His playbook of moves is ever larger than when he first sailed out to sea. He has contacts in various ports that can help him if something were to happen. More than anything, he has seen many more situations than we he started. He has seen things go wrong. He has seen things break. He is a swiss-army knife of solutions able to tackle issues that inevitably arise.
Knowing the body of water
The sea is the market. Sometimes favourable, often rough, occasionally unforgiving. A good skipper know his boat, but he also knows the body of water where he must sail. He is able to compose with the conditions of the sea, good or bad, that day, month or year. He can hack his way through the waters to further along his course.
Even when he knows his course, he will typically need to tack frequently to change the boat’s direction to combat the headwind and remain on course. Staying still is not an option at sea. When the boat leans on one side during a maneuver, that will be a intense but exciting feeling. It will be a lot of work and schleps, but when the crew finds the fit between their vessel, the winds and the sea, the sailing gets smoother.
However, every body of water is different. While his sailing experience and skills will generally transfer from one body of water to the other, there will be learning and adjustments. In the uncharted waters of new markets, often only the most experienced or naive are brave (or foolhardy) enough to venture out to sea.
Weathering the storm
The storm comes. It always comes. The headwinds pick up. The sailboat does its best to fray itself a course through the choppy waters. The skipper battens down the hatches to avoid the water spilling into the boat. The spill is hard to contain. He does his utmost best to keep morale of the crew high, but the storm has taken a toll on him as well.
In an echo to Ben Horowitz’s excellent post Peacetime CEO/Wartime CEO, the peacetime skipper then becomes the wartime skipper. He must make hard choices. He will find himself at times between Charybdis and Scylla, the mythical sea monsters, needing to choose the lesser of two evils. In Homer’s Odyssey, to pass through the strait, the hero opts to pass by Scylla and lose only a few sailors, rather than risk the loss of his entire ship in the whirlpool. In those moments, there is no lonelier job. After some time, the storm passes and the crew lives to sail another day, with one or two more battle scars.
Managing downtime
While there is no rest for the skipper while on the sailboat, there is downtime on land between trips. For charter-boat skippers, sailing is a seasonal occupation. For racing skippers, sailing is bursts of activity with periods of downtime interspersed. That said, if the skipper has not taught his crew members to become leaders, moments of downtime may however generally may be fewer and far between.
Managing downtime between ventures is a key leadership skill for entrepreneurs. David Gergen, a Harvard professor of public leadership, refers to these times as “being in the wilderness”. In a recent Forbes article, he mentions that “these periods in the wilderness offer opportunity for growth, development and even reinvention, likely leading to the path to becoming who you’re meant to be — your most authentic self”.
In the down season, the skipper repairs his boat. He reads books to learn about the universe. He might take a personal break and invest more time with his significant other, friends and family. He knows that on the boat, a balanced life may be very hard to find. He may also not fully know how long his next journey will be. That said, during downtime, he still often has an eye out to sea, daydreaming about his next adventure.
A man and the sea
While there is the sacrifice of being alone with your crew at sea, away from the world, there is also infinite joy. There is the feeling of freedom, of independence, of creating your own destiny, of charting your own course.
This freedom comes with a responsibility. At the end of the day, the skipper is accountable for the victory or failure of his vessel’s quest. He is accountable for the sailboat reaching its course. Sometimes he will fail — and that is OK — but he will have garnered stories and experiences that will inform his future periples.
“I must down to the seas again, to the lonely sea and the sky,
And all I ask is a tall ship and a star to steer her by”
- John Masefield, Sea Fever
In the end, there is a sweet irony. While the destination was the original impetus for lifting anchor, it will always be more about the journey than the destination. For the sailor, as noted Longfellow in his classic poem, it is the thrill of the great ocean that sends a pulse though him. It is and will always be about the adventure, about conquering the wide open blue sea.
Photos: LP Maurice
Note: Thanks to my colleague Thomas Geissmann for his feedback. Thanks also to all the expert sailors that I link to in my essay that have shared valuable lessons about their adventures at sea for other younger skippers to learn from.