A CEO Ditched Everything He Owned To Sail Around The World For Almost 3 Years

Three little birds dolphinsScott Leonard / Three Little BirdsThe boys admire friendly marine life off what the coast of what Leonard believes to be St. Kitts. ‘It never gets old, having a visit from some dolphins,’ he says.

In 2011, Scott Leonard moved his family of five onto a 50-foot catamaran called Three Little Birds.

He sold his Southern California house and all of the furniture in it; gave away or donated nearly all of his three sons’ toys; and made arrangements to remotely run his wealth management business.

“Getting rid of everything was actually really liberating,” Leonard says. “You don’t realise how much stuff you have until you get rid of it.”

Leonard flew home once a quarter to meet with clients, but otherwise managed his business from the boat. He shares the infrastructure he created to do it in his book, “The Liberated CEO: The 9-Step Program To Running A Better Business So It Doesn’t Ruin You,” but here, he shares something even more fun for those of us who are desk-bound: photos from his adventure, illustrating how his family learned to live with less.

Leonard, his wife Mandi, and their sons Griffin, Jake, and Luke — who were 10, 9, and 4 when they set sail — spent two and half years abroad, visiting everywhere from Panama to St. Kitts and Nevis to French Polynesia.

On the boat, Leonard remembers, the boys’ only toys were Legos. “Part of what the kids learned was how to play with what’s in your environment,” he says. “Most places we visited were pretty poor countries, and if they had one ball in the entire village it was a luxury for them.” The boys explored, climbed, leapt, paddle boarded, and tubed.

In fact, Leonard found, the trip was surprisingly budget-friendly. “Travelling on a boat, there really wasn’t much to spend on,” he recalls. “No sports events, no concerts, and in the South Pacific, we didn’t eat out much.”

His favourite memories of the trip were similarly low-cost: a two-hour family dinner every night, which they had rarely managed to do at home between all of the boys’ after-school activities. “Watching the sun set together as a family, every night, was one of the most special treats of our trip,” remembers Leonard.

“The highlight of the whole trip was the time together,” Leonard says. “It was kind of like the boys had no choice but to talk to us. I think whether or not they appreciate it now, that’s going to be one of the greatest aspects of the trip.”

Today, the family is back home in California, while Three Little Birds awaits its next owner in New Caledonia.

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