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Closing The Loop: Dana Greyson

Warren Miller

Dana Greyson has lived most of her life in the Pacific Northwest. In 2005, she met her husband, Walt, through a friend. 

“He asked me to go sailing,” she said. “I’d been on a sail boat a few times, but this was a cruise to the the San Juan Islands.”

Dana and Walt became a sailing couple. Each had been married before, but had no children. Wayne is a contract aircraft mechanic. Dana had worked for Hewlett Packard, but her division was cutting staff. They had few ties to dry land.

“We were in Everett, Washington in 2010, and one day – out of the blue – he asked me, ‘What do think about chucking everything, buying a boat, and sailing around the world?’”

Their plans developed. In 2011, Wayne flew to St. Lucia in the Caribbean to buy a sailboat. They sailed it from St. Lucia to Jacksonville, Florida, where Wayne had found a contract position working on commercial jets. They arrived in summer 2013 to escape hurricane season in the Caribbean, and they’ll stay until December 2014.

They plan to spend two years sailing, with no idea of where they’ll go or what they’ll do after that.

That’s given them time to prepare their boat ? as well as themselves ? for leaving dry land behind. Their legal residence will be a friend’s home in Vancouver, Washington. That friend will review their mail, scan what they need to see, and contact them by email or satellite phone. They have a financial planner, and have seen all of their doctors and dentist.

They’ve reduced their possessions to five boxes of photos and high-school yearbook that will remain at a family home. Other than that, the only things they take with them are what’s absolutely needed to live in 150 square feet, with – depending on the moment – either no backyard or the entire world at their door.

Even more important is the mental and emotional preparation to live in an uncontrolled environment.

“It’s a letting-go of any familiar routine, people you can talk to whenever you want,” Dana said.

Dana and Wayne have no destination, only the voyage itself.

“What we’re trying to figure out is where we’re going to land.”

Warren Miller is a writer and financial executive who lives near St. Augustine, Florida.