First Mate, J.D.

In 2016, Amanda Butler Schley made a bit of a career move. She not only left her job at a large law firm to found her own boutique, Business Law Group, focusing on representing entrepreneurs, she also sold her home and most of her belongings and moved onto a sailboat.

The question on her mind was this: Can lawyers truly work from anywhere?

She discovered the answer over the next year while sailing her way down the Gulf of Mexico with her two dogs, Ava and Kadan, and her boyfriend, Rob. “He was really the captain and I was the first mate,” says Butler Schley. 

Their vessel, Stay Foolish, was a 44-foot Island Packet 420 sailboat, also called a monohull sailboat. It had two bedrooms, two bathrooms, and it was designed for long-term “blue water cruising,” as opposed to shorter excursions like coastal sailing. They officially set sail from New Orleans in December 2017. 

“The plan was to go all along the Gulf Coast,” she says. “We didn’t have any place we had to be at a specific time. We were just going to let the adventure take us where it would.” 

She maintained a loose work schedule, and tried to avoid sailing during the work week, so that she could attend to sailing tasks—and so they could chronicle their eastward journey on Facebook. Since some previous clients came with her when she opened Business Law Group, she didn’t need to focus on bringing in new ones—although the adventure itself helped drum up business. 

“I’ve literally had three or four people who are sailors or entrepreneurs call me just because of my story,” says Butler Schley. “I think that the story resonates with the type of clients that I look for.”

They made about 20 stops during their trip. Some of her favorite spots included the “little, small artists’ town” of Apalachicola on the Florida panhandle, and “the famous pink hotel” in St. Pete Beach, Florida, which offered services that made digital nomading easier. 

Six months into their adventure, on Butler Schley’s birthday in June, Rob surprised her with a marriage proposal, and the couple began to brainstorm ways to work their wedding into the journey. They wanted to have a destination wedding on the island of St. Lucia in the Caribbean, but time was working against them: “Every time hurricane season comes, you really have to have a good hurricane plan,” she says. Ultimately, they decided it was safer to leave the sailboat in Florida and fly to St. Lucia for the wedding in October 2018. 

After the ceremony, the newly married couple reevaluated their sailing adventure. 

“It took us pretty much a full year to get from New Orleans to St. Petersburg, Florida,” says Butler Schley. “We just realized that, if we were going to try to get from there to the Caribbean, we were going to encounter a bunch more problems.” 

They decided to take a year-long break from sailing, and went back to New Orleans, leaving the sailboat in Cape Coral, Florida to charter to other southwest Florida sailors. The dogs surely appreciated the change in plans. “The boat literally feels like you’re standing on a washing machine, and the dogs were extremely unhappy,” she says.

Then, before they got back on the water, the COVID-19 pandemic hit. As interest for chartering sailboats declined, the couple started to receive more offers to buy their boat. They ended up making a tough decision: “We sold Stay Foolish just last year and ended up moving back onto land full time,” says Butler Schley. “Now we’re living in the Garden District in New Orleans.” 

They’ll never be landlubbers, though. “We’ll continue to sail for the rest of our lives, but probably be doing more sailing in a charter capacity and less as full-time cruisers,” says Butler Schley. 

And while Business Law Group is thriving, she doesn’t expect to work as a full-time lawyer on a sailboat again. “I think our biggest takeaway is that ‘destination happiness’ is a false premise, in that ultimately home is wherever you make it and happiness really comes from within,” says Butler Schley. “Which is a huge lesson because it really actually guides all of our decisions at this point.”

All told, the experience was life-changing. “Even though I had lived in New Orleans for many years, and I had traveled all along the Gulf Coast, you never see anything from the vantage point that you see it when you’re in a boat,” says Butler Schley. “You get a totally different perspective, and a really valuable perspective.