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Seven at Sea

How Emily and Erik Orton transformed their cramped city world into an unforgettable adventure

Humans, by nature, are careful creatures, always looking for the answer, trained to detect anomaly, to find and isolate threats. But how often do we miss the beauty that awaits us? Our imaginations are often filled with everything that could go wrong. How many of us are brave enough to ask, what could go right?

Emily and Erik Orton are two such heroes of possibility, and with their five children, allowed their dreams to propel them from the cramped quarters of their New York City apartment to an unforgettable, year-long sailing adventure. Their experiences are detailed in their book, “Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat,” which became a best seller. Emily was a former English teacher and writer, and Erik is an Emmy Award-winning writer and produced musicals Off-Broadway.

Now living in Utah, the Ortons shared their transformative mindset and their vision, the impact on their family and their lives, and what they are doing to help others achieve positive perspectives.

"We had started to ask ourselves these blue-sky questions,” explains Erik. "What would you do if money were no obstacle? What would you do if you knew you would succeed? What would you do if you weren't afraid?”

Feeling bogged down in the typical midlife malaise, the Ortons experimented with techniques to keep their time meaningful: setting aside a single day a month of totally unstructured time, singing songs as a family, having sessions of silent eye contact.

Elaborating on their burgeoning philosophy, Emily explains, "Every time we do something in a new or unfamiliar way, it opens up room for growth and connection." This process can disrupt the dreadful inertia that creeps in, creating experiences that are seared into our minds and memories. "It's almost like a magic trick where you can expand time," adds Emily.

A product of this effort to breathe new life into tired routines was the prospect of sailing the Caribbean and Atlantic as a family. At the time, it was near-impossible to imagine the trip as a possibility; they had no boat, funds or sailing experience, and to top it off, Emily was afraid of deep water.

Says Erik, "It was very gradual. It went from, maybe I can take a beginning sailing lesson, to advanced sailing certifications, and eventually, experiment with renting a boat.” In a short time, they realized, drifting away from the Manhattan skyline during their first day trip, that the beautiful, thrilling dreams they had once entertained as fantasy were on the horizon.

How did the voyage impact their children?

"The kids actually had more separation on the boat,” Emily says enthusiastically. Having been packed together in two bedrooms, the four matchbox cabins on their newly purchased boat were a welcome upgrade to a family already tightly tied together. Yet the trip managed to bring them together in a way that even they could never have thought possible.

Their first leg out to sea proved to be a success, traveling from New York City to St. Martin, the Virgin Islands, the Bahamas, and back again.

"Once we did this sailing trip, we realized there was a pattern to how we did these things,” Emily explains.

After figuring out how to articulate that pattern, they peered into the structures of possibility, bringing other dreams into the light. They went to Bermuda, French Polynesia, the Mediterranean, Hawaii, and New Zealand, and even attempted an Atlantic crossing.

When asked how these experiences could be replicated, Erik and Emily eagerly share what they've learned. "A lot of people say, oh, I'm not adventurous. But having a family is a big adventure in any circumstances," Emily quips.

Erik emphasizes: “The key is not the budget, the setting, or the timeframe; it's the mindset. It's possible to create those kinds of circumstances—bonding families, making lifelong friends—in a variety of settings.”

Emily and Erik are careful to point out that transforming your experiences can happen in limitless ways. Erik continues, "It's not about trying to inspire everybody to go live on a sailboat; it's about trying to help as many people as possible have these growth experiences that connect them with their family, under whatever circumstances are possible under each home."

Erik and Emily are now engaged in a project called, “The Awesome Factory,” where they offer guided trips similar to the one they undertook. “It's three things: an incredible vacation, learning how to sail, and family coaching, where we go in-depth on the mindset, tools and systems we used to get us on our sailing trip, and to do almost every major thing in our lives since then,” says Erik.

Erik sums up their philosophy like this: “Define what matters most to you, push past fear and excuses, and ask yourself, what could go right?”

Their next trip is to the Sea of Cortez, which may be followed on Instagram at @theawesomefactorynyc. They also launched a weekly podcast in June, “What Could Go Right?”

"Every time we do something in a new, or unfamiliar way, it opens up room for growth and connection." – Emily Orton

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