In 1998, James Green became a founding partner of an ad serving company; within 18 months it had sold for $70 million. After that startling success, though, the next decade of Green’s career was a slow downward spiral. By 2008, he was deeply invested in a struggling company, and losing money hand over fist. He was miserable, stressed, and spectacularly burnt out. He began to look for a way to sell the company, and during the process he told his wife, screenwriter Emma-Kate Croghan, "Honey, we’re losing more money per year than it would cost us to live on a sailboat."
It may have seemed no more than an observation at the time. But Green was also speaking to a lifelong passion. His father had taught him to sail when he was a kid, on a manmade lake in England. His father had a dream of going on a long sailing adventure, and the idea, recalls Green, "had infected me."
By early 2009, Green had amassed a stack of boating magazines by his bedside that Croghan began referring to as his "boat porn." ("I would look at the pictures and get very excited," he explains.) It all still seemed utterly unreal. Green and Croghan had two young children, Paloma and Ronan, in lower school in New York. And who took off to sail for a year? Surely it was career suicide, if not another kind of suicide. (Green had never captained a vessel before.)
But by August, the project seemed real enough that the family rented a catamaran on the Chesapeake Bay for two weeks. They had a blast. In October, Green managed to offload the company, taking a job at the acquiring firm. "That’s it," he said. "I’m going to find a boat."
Green settled on a 55-foot catamaran, and in May 2010, he sailed it from Florida to New York—his first long-distance sailing trip, and the first to go more than 100 miles from shore for any significant stretch of time. He hired a friend of his to captain the boat, while Green watched and learned. In July, he informed his boss that he would be taking a sabbatical in the fall.
The boss looked at him quizzically. "We don’t allow sabbaticals," he said.
So Green clarified: He was quitting.
The first leg was from New York to Bermuda, but it kept getting delayed due to weather. Finally, Croghan and the kids flew out to Bermuda, while Green waited for a window of decent weather. He tried to hire a professional crew to sail with him, but he had trouble finding any who were comfortable sailing with a first-time captain. At last he found two people to join him, and got an alert from a professional weather forecasting service. The forecaster informed him that despite the fact that it was snowing in New York, Green had a narrow window to set sail immediately, if he was to avoid storms ahead.
"I had never sailed in the snow before," he recalls. "I had never really experienced any kind of storm conditions, and it was my first time captaining in the ocean. It was exhilarating."
Green rejoined his family in Bermuda, and then they set sail for Antigua. It was on that journey that Green hit his first major challenge as a captain, on Thanksgiving Day. Green was on the 4 a.m. to 8 a.m. watch, when he realized the boat wasn’t steering properly: indeed, it was going around in circles. He tried calling for support in the U.S., but no one answered. Looking down at the rudders, he saw that one of them was not aligned, and wouldn’t budge. Something seemed deeply wrong with the hydraulics.
Croghan had the idea to call a boatyard in the Caribbean. Someone answered, and walked Green through the complicated series of maneuvers to fix the rudder. After hours of despairing and fiddling, finally the rudder locked into place, and the boat resumed its course. "I’ve never been so goddamned happy in my life," he recalls. "That was my first ‘Captain Dad’ moment."
The next month, Green’s own father fell critically ill. The family anchored the vessel—which Croghan had named Ondine, after a mermaid myth—in Martinique, and Green flew up to Vancouver to see his father. Born in 1920, he was a reserved Englishman who had never clearly communicated to Green that he was proud of him. But as friends and family gathered around him, Green's father was "gushing," Green recalls, "about how his son was sailing for a year, and was going to cross the Atlantic, and how proud he was."
There were three principal goals for the journey. The first two were Green’s: He wanted to sail for a year, and he wanted the major challenge of crossing an ocean. The third was Paloma’s, who was then 10 and obsessed with Greek gods. She wanted to see Greece.
If Green wanted a challenge, he got it. He was sleeping off a long night shift somewhere in the middle of the Atlantic when a friend of his, along for the crossing, came below deck, white as a sheet. Green's friend dragged him up on deck and pointed out over the water. "What the fuck is that?" he asked.
Green knew what it was: a waterspout. A massive, twirling column of air and water: the ocean’s version of a tornado, and just as destructive.
Green’s friends wanted him to drop anchor so the Ondine could hunker down while the storm passed. But Green had been reading about how to handle storms like this one, and he decided to change course, trying to harness the power of the storm to escape it as quickly as possible. At one point the ship was traveling at 18 knots, twice as fast as the vessel usually hit at top speeds. "We were putting up a wake like a speedboat," he says. Waves crashed around them, and the boat started to leak in places.
Finally, the wind died down, and though the sea remained choppy for a spell, Ondine had made it to safety.
The Azores—their destination on the other side of the Atlantic—wasn’t far off. When they arrived, they upheld the tradition for crossing vessels there of painting a picture of the Ondine along the pier.
A visit to Greece soon followed, achieving Paloma's goal.
Green readily acknowledges that not everyone can claw together the capital to make a yearlong sailing trip work. But he thinks many people can—and should—take a sabbatical of some kind, and he urges them to set goals, like he and his family did. "It needs to have some purpose," he says, suggesting that you document your steps towards that journey as you go. "If you’re just taking time off at the beach, it doesn’t have the same affect."
Around the time the family hit Greece, they also ran out of money. Green was now "literally impoverished," he says, having raided even his retirement account and borrowed from a friend. It was time to go back to work.
He was fantastically ready: He was recharged like never before, brimming with ideas. Not that his trip had been relaxing; it had been filled with stress and peril. But he had set a goal, and reached it, and this is what energized him.
Green feared that he would be forgotten during his sabbatical, and unemployable upon his return. But the opposite proved to be true.
"It turned out to have been a brilliant marketing move," he says now of Ondine's voyage. Previously, someone scanning his LinkedIn page would have seen a decidedly mixed bag. But this ocean adventure—which he had chronicled through the year on a blog—added a new sheen to even the duds that had preceded it. "I was immediately positioned completely differently, as someone having the courage to go out and do something." People had forgotten his last company’s dismal sale. "No one remembers two years ago," he says. (Green joined the ad targeting firm Magnetic in 2011 as its CEO, where he happily remains.)
In those initial interviews upon his first return, everyone asked him about his adventures. What had he learned? What had made the trip most worthwhile? He’d tell a story about how he had to dip into reserves of courage, or how sailing was a challenge that was equally mental and physical.
Later, though, when he thought about his responses, "it felt hollow," he says. Because he knew that what he most valued was the joy of spending long, unscheduled days with his wife and kids. History lessons came to life for Ronan when the family visited French and English forts in the Caribbean, and a basic trigonometry lesson was made practical while explaining navigation to Paloma.
After those interviews, he asked Paloma what she got out of the trip. "I got to know you, Daddy," she said.