Telecommuting from paradise


Waves gently lap Caribbean sands — as you write a memo.

Cicadas sing from your rolling farmland — as you take a conference call.

Squirrels scrounge up a feast in your garden — as you send a text.

Want to join the ranks of people who telecommute from paradise? If you don’t have the means and the discipline, you’ll have your work cut out for you.

“While most [working] people use the Internet to escape, I just look at the critters or Buddha in my garden,” says Kendra MacLeod, who lives in Lenox.
“While most [working] people use the Internet to escape, I just look at the critters or Buddha in my garden,” says Kendra MacLeod, who lives in Lenox. handout

Kendra MacLeod is particularly Zen about her experience.

“It’s really nice to gaze out at flowers rather than concrete,” she said of her home-office view. “I set up my desk in the kitchen because it had a big picture window there. While most [working] people use the Internet to escape, I just look at the critters or Buddha in my garden.”


She recently sold her Sylvan Learning Center in New Jersey after working remotely — and happily — from the home she purchased as a vacation and retirement property in the Berkshires community of Lenox. The discipline required (such as setting and sticking to specific hours) may not be for everyone, but MacLeod said the arrangement increased productivity for both her and her employees.

“The boss is the center of everything that happens, and everything is deferred to me, even if I didn’t really need to participate in the decision-making,” MacLeod said. “My employees grew and became more independent in my absence.”

Gail Roes, however, is inching toward retirement but still working from her vacation home in Sarasota, Fla. When her family visits from Boston, New York, and the Midwest, the children see Grandma in action — and a balance of work and play. They often head south during April school break — unfortunately, that’s around tax season, her busiest time as a certified public accountant.

“The toughest thing is the external pressure of people who thought I should be able to drop my work today and go shopping or golfing,” Roes said of the initial reaction by some acquaintances. “I can do that occasionally, but not consistently.”


What she does like is the desktop-sharing technology that allows her to transfer data and files remotely and to maintain relationships with clients she has had for about 25 years. Working from the Sunshine State was the perfect compromise when her husband was ready to retire.

“He did, and I wasn’t quite ready,” she said. “I can’t just drop clients into someone’s lap. . . . They don’t want me to go, and in a way, I don’t want to go.”

For Maggie Fearn, owner of the corporate public relations consultancy Fearnace Media, other technologies like Skype and FaceTime can make lengthy conversations with her Australian clients even more effective than the traditional business call.

“With the video component, it’s much easier to get a read on ... how a discussion is going, whereas sometimes on the other end of a phone, you wonder if they’ve wandered off,” said Fearn. “Faces add an important dimension to every conversation.”

After 18 years in Australia, Fearn and her husband, Greg, moved to Cape Cod last year to be closer to family, and are remodeling a 1980s ranch house to incorporate their dream offices.

“The point is never to make it overly office-y,” Fearn said. “It has a built-in cupboard and fireplace, with a deck to see beyond the trees. It’s really restful.”


While that may work for some small-business owners or independent contractors, the size of the company has to be just right, said Bob Verrico, cofounder of Investing Channel, a Manhattan-based media company whose sites reach 18 million individual investors and financial professionals. Verrico sometimes works from his 25-acre farm in Morristown, Vt.

“Because we are a small, ‘high-touch’ company [of] only 35 people, it really makes a difference that everyone is there,” he said. “There is a lot of daily interaction in our type of business, so when working remotely from my Vermont home, I am on the phone pretty much all day to maintain a level of communication as if I was in the office. Obviously, it is not quite the same as being there.”

Some larger companies, however, have policies that make working from home — or a vacation spot — an attractive benefit and recruitment tool.

State Street’s Flex Work option has programs that allow employees to work remotely, for shorter hours, or at different starting and ending times. The capability to put in time without having to wear a tie has made for a more satisfied workforce, said Michael Scannell, senior vice president of global human resources. While it may not be feasible for every role at the financial services company, a 2014 employee engagement survey indicated that nearly 70 percent of its global workforce had access to Flex Work and that those workers had 47 percent less turnover than State Street’s overall rate. The employees collaborate with their supervisors to determine what is right for them and for the company, Scannell said.


The attraction of working from home is no surprise to businessman and philanthropist Ernie Boch Jr., who built offices and upgraded technology at his vacation homes in Martha’s Vineyard and Nevis in the West Indies.

“Working in a vacation home, there’s a certain kind of energy you don’t get at the office. You’re still conducting business, but it’s even more enjoyable, probably because you’re not tied to a desk.” said Boch, who owns 32 businesses. “It’s a good thing for the mind and the spirit. It elevates your game when you get back.”

Although Kendra MacLeod is out of the game now that she has retired, she did briefly consider buying a Sylvan Learning Center in the Berkshires. But having brick-and-mortar work near her vacation space would be a little too close for comfort.

“I always said I didn’t want to turn my refuge into my work.”

Carley D. Thornell is a writer born and based in Boston. Send comments to Address@globe.com.