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John Bailes on the Sea
Sommerville Journal in Eastern Mass
November 18, 1999

Out of the armchair, into the sea

Photo caption: John Bailes
John Bailes is not your typical financial planner. At least not anymore.

The six-days-a-week, ought-to-own-stock-
in-coffee, home-after-the-kids-
are-in-bed lifestyle no longer defines John Bailes. That's because on a heavy-trading midweek afternoon like, well, yesterday, the 47-year-old Somerville resident drove to Huntington, N.Y. so he could crew a boat delivery to Ft. Lauderdale, Fla.

This is no mid-life crisis, mind you. John Bailes has fantasized about swashbuckling the high seas since early adolescence.

It's just that, as Bailes puts it, "School, sports, aptitude tests, the reality of growing up and becoming an adult intervened ... the dream of being a sailor receded in the clamor of opportunities and responsibilities vying for attention."

The quote is an excerpt from Bailes' Web bio, which resides at, home page of the governing and organizational body for the "world's toughest yacht race," the BT Global Challenge. Bailes' bio is not some signpost on the information superhighway soliciting new client portfolios, though tapping him for tidbits might not be a bad idea: Bailes will pony up $41,000 for his involvement in the race. The bio exists because next September, as an amateur sailor who tied his first sea knot in earnest only five years ago, Bailes will serve as one of 17 crew members on a 72-foot yacht racing over 30,000 miles of ocean against prevailing winds and currents.

Simply put, he'll be going the wrong way. Talk about buying in a sellers' market.

"(I guess I was thinking) something stupid," quips Bailes, who will be assigned to a crew and a boat on Jan. 8 at the London Boat Show. "It's going to be like jumping off a cliff because no matter how much you think about it or prepare, you never know how it's going to play out."

Given the dicey conditions the dozen or so racing yachts will face next year, Bailes might graduate to cliff diving with ease. On the round-the-world, 10-month journey, which is scheduled to set sail from South Hampton, England on Sept. 10 of 2000, Bailes will be asked to set a course into the teeth of average wave heights cresting at 40 feet and wind gusts of 65 knots.

"I'm just working my butt off to be in tip-top shape, physically and mentally," says Bailes. "I've had a major [BT Challenge facilitated] crash course in becoming a seaman, but I'm doing this so (in the future) I have the chops to sail a boat anywhere. We'll have all the latest technology on board. Of course, that makes you feel somewhat safer. But when the s*** hits the fan, it hits the fan."

Bailes earned the privilege to be a BT Global Challenge crewmember thanks to a single, arranged interview with a BT Gobal Challenge coordinator at the Atlantic City Boat Show in February of 1998. "It went off quickly, smoothly, humorously and sincerely," says Bailes.

A month later, he aboard his first training voyage, negotiating icy decks and lifelines off the coast of Norfolk, Va. Not too shabby for a guy who began casually following yacht racing three years ago as a recreational member of the Boston Harbor Sailing Club.

"There are a lot of considerations that go into choosing a crew member," says Claire Smyly, crew volunteers' manager at the UK office of Challenge Business. "(John absolutely) fits those criteria. He's very committed and as we put the teams together, we're very excited to have his name on the list."

Bailes, who calls himself "part of the Sputnik Generation," is furiously sorting out the myriad of business, personal and financial ramifications of crewing the race, which will make stops in Boston, Argentina, New Zealand, Australia, South Africa and France before returning to the UK. Not the least of those tasks is keeping his wife, Jesa, smiling about his new alter ego as an able-bodied seaman.

"We have a very strong relationship," says Bailes. "We really support each other with the things that mean a lot in each other's lives. To be honest, she knew how much this meant to me before I did."

More information about the BT Global Challenge can be obtained at the race Web site or by emailing John Bailes at

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