House For Sail

The O'Gorman family. Photo by Michael Heller

As co-founders of a life coaching business that caters to successful executives, Catherina and Gerry O’Gorman know what it takes to help their clients rediscover what is oftentimes missing from their lives: happiness.

They encourage their clients to unplug from their daily routines, affording them the opportunity to turn their gaze internally so they can figure out what is preventing them from living the lives that they believe they should be leading — and then assist in the plotting of a course around those obstacles.

It is typically a difficult task as those seeking their services must first learn to break away from their “fear-based thinking,” as Mr. O’Gorman describes it, a deeply ingrained and automatic default for most who are taught, usually starting in childhood, how they are supposed to behave and act to meet society’s self-inflicted

“We’re breaking the old belief of who we need to be,” said Ms. O’Gorman who, with her husband, founded Think Love University weeks after they met in 2006. “The only thing we need to be … is to be true to ourselves.”

While he and his wife have helped many clients achieve that very goal, through intense counseling and much soul-searching, Mr. O’Gorman is the first to acknowledge that he was not practicing what he was preaching.

Well, not entirely.

He did make definitive steps in that direction by resigning as vice president of a successful executive search recruiting business run by his family and, later, moving into the Sag Harbor home that he originally purchased as a real estate investment with his brother. Though he and Ms. O’Gorman, both of whom left long-term marriages following a chance meeting in Fiji in 2006 in which they fell deeply in love, bought out his sibling and moved into the home a decade ago, a huge part of Mr. O’Gorman’s transformation remained in a holding pattern.

Ever since he was a child, he always had an affinity for the ocean, longing to one day completely uproot himself and sail around the world. That unfulfilled dream continued to haunt him as an adult, when he worked in a “soul-destroying” environment, as his wife describes his former fluorescent light illuminated confines in Hicksville, an office in which a photo of a sailboat remained affixed to a wall.

“I always felt that it wasn’t true for me. I always knew there had to be something else,” Mr. O’Gorman said of his previous career. “I always thought about sailing a whole lot.”

He and his wife took the next significant step together when they agreed this spring to put their Peninsula Drive home on the market for just shy of $1.7 million, setting aside nearly $700,000 of the pending sales proceeds to buy Mr. O’Gorman’s dream sailboat, a custom-built 45-foot Lagoon 450 Catamaran.

Their four-bedroom home, which stands less than a block from the water and is all white inside, is listed with Carol Nobbs of Douglas Elliman Real Estate. As intended by its owners and described in the listing, the roughly 2,000-square-foot ranch is a “sanctuary” of sorts, observing that “there is some special magical loving energy here.”

On any given day, the couple’s bicycles can usually be spotted adorning the front porch, unless they’ve ridden them to the nearby beach to enjoy the views or to go paddle boarding.

“We’re stepping out on faith,” said Ms. O’Gorman, explaining that they are receiving a bridge loan through a connection from a former wealthy client until they sell their home in the village. “He’s healing himself … it’s an actualization of his own personal dream,” she continued, referring to her husband.

The Lagoon 450 is Mr. O’Gorman’s ideal sailboat as it is small enough for he and his wife to handle on their own, but spacious enough to accommodate them and their 2-year-old chocolate Labrador, Harry, and their rescue cat, Daisy. The main selling feature was the sailboat’s elevated flybridge, a relatively new concept for
Catamarans, according to Mr. O’Gorman. The couple had rented similar models a few times while visiting the Caribbean, both while assisting clients and for pleasure, and knew it would be their only choice whenever they decided to make the leap from dry land.

That’s not to say that they are not concerned about adapting to a life on the water, or crossing an ocean on their own for the first time. The purchase process for their dream sailboat has already underscored an important lesson for those who live on the sea: one must be able to quickly adapt to unexpected and sudden changes, and not just due to the often unpredictable weather.

Though they initially intended to pick up their new purchase in France where it was built, sailing it around the Mediterranean Sea and hitting several Greek islands before heading back to the states, those plans are now in flux. During a recent interview, they explained that they now might accept delivery of the sailboat in England, and are still debating whether they want to sail it back themselves or have it shipped to a port in Rhode Island.

“We’re able to shift and go with the flow,” Mr. O’Gorman said. “Another metaphor of sailing is that you sometimes have to reset your sails.”

Once they are stateside with their Lagoon 450, the still-tentative plan is to make stops at old seaports along the East Coast while slowly making their way to the Bahamas. They then intend to continue through the Caribbean, making several more stops, before navigating the Panama Canal. The longer-term goals include stops on
the Galapagos Islands before continuing west to the Polynesian Islands.

Regardless of how it gets there, their newest purchase will eventually be temporarily anchored in the harbor off Sag Harbor—at least for a few weeks. But they intend to pull up anchor before summer’s end.

“We all have a dream and most of us are disconnected from our childhood dreams because we are conditioned to be solvent in our minds,” Ms. O’Gorman said. “The American dream, it’s been so distorted.

“The universal dream is to live your truth,” she continued. “What’s true for you. For Gerry, it’s to live aboard a sailing boat. It might be for the rest of our lives or it might be for six months. We don’t know.”

What she is certain of is that she can live anywhere, and find happiness. “I’m in a state of love wherever I am,” Ms. O’Gorman said, “and wherever I am, I am a loving individual.”

And she’s traveled extensively, both as a child and an adult. Conceived in Australia and born in India, Ms. O’Gorman said she spent most of the first four years of her life on the ocean. The daughter of a cargo ship captain, she and several of her six siblings, as well as their mother, lived on the ocean before their parents, Cedric and Romayne, settled in New Zealand. Ms. O’Gorman said her father later suffered a series of heart attacks, with the third one claiming his life at age 53.

Though it was a faltering heart that took her father’s life, Ms. O’Gorman believes that a huge part of him slowly withered away once he was removed from his natural environment, the ocean.

It is the same entity that she believes will now allow her husband to find his true happiness, something that he denied himself for years while focusing on doing what he falsely believed was the right thing to do.

“You always see these bumper stickers saying, ‘I’d Rather Be Sailing,’” Mr. O’Gorman said. “It cannot help but create resentment.

“Most of us are living with these inner conflicts, and there’s a little kid inside of us who just wants to go sailing.”