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Reinventing Your Job

How to work your way through your bucket list

By Frances Donington-Ayad

Sienna Whittans, 23, grew up in paradise and got sick of it. Born and raised on The Big Island in Hawaii – a destination most spend thousands of dollars to escape to – she loved her home and its beauty, but saw the drawbacks.

“Growing up in Hawaii, you’re in the middle of the ocean. You’re so cut off from everything else,” says Whittans. She didn’t really conceptualize all of this until high school, when she had the opportunity to study abroad in Switzerland for a few months. “It was my first long term situation where I didn’t speak the language, didn’t know anyone. That’s when I was like: I like this,” she says. From there her goals became clear: leave ocean-locked Hawaii and find the means to live abroad every day. But Whittans didn’t want her desire to explore different countries to turn into just a hobby, reserved for one or two vacations a year. She wanted to make living abroad her career.

Whittans’ first step towards this was attending Simmons College in Boston and pursuing a degree in International Relations. But after graduating, Whittans struggled with finding the money and visa clearance needed to live abroad in the way she dreamed. She had to begin strategically planning in a different way. She researched scenarios that would allow her to not only live in foreign places for an extended time, but also work there and gain an income along the way.

She researched scenarios that would allow her to not only live in foreign places for an extended time, but also work there and gain an income along the way.

That led to Whittans living in Ireland for a year post her college graduation on the J1 Visa, a program that allows American citizens to live and work in Ireland for a year, and vice-versa for Irish citizens in America. She held jobs in bars, restaurants and nightclubs. After that she applied to work at an organization that connects English speakers with schools around the world. She’s currently in Thailand, teaching English to middle school students, living in a furnished apartment for $150 a month. Whittans is confident that her long restaurant resume, paired with her new teaching experience, will open up jobs in foreign markets for a long time to come.

Not everyone is as lucky as Whittans. She tackled the biggest items on her bucket list with a clean slate: 23, healthy, no kids, no house, no long standing career, no commitments. But what about those who have careers, commitments and responsibilities?

Thomas and Monica Abend were two such people. The recently married couple was living in New York, working promising careers. But Monica, who was the Dean of a school, was ready to try something new. Transitioning careers can be a source of great stress and uncertainty, but instead, the couple saw it as an opportunity.

He was also able to arrange with his employer to work remotely for an unassigned period of time.

Thomas and Monica had dreamed of living abroad and country hopping for a long time. They wanted to tour through New Zealand, live in Mexico City for a month, and watch friends in Canada get married. “We’d thought about all the places you can go not on a teacher’s schedule,” Thomas says. So with Monica’s decision to transition careers, they did just that. The couple bought tickets, left New York, and embarked on one of their most exciting life goals.

Thomas Abend clocking in from Auckland, New Zealand.

Monica’s professional shift was not the only factor making this trip possible. Another big reason was Thomas’s job as a software engineer. He was also able to arrange with his employer to work remotely for an unassigned period of time.

Working remotely is a growing trend in the tech industry. Since 2005, the number of telecommuting jobs done remotely in the U.S. has gone up 140 percent, according to 2005-2016 to the U.S. Census Bureau. “It goes along with the popularized idea of being a digital nomad,” Thomas says, a.k.a. people who travel, live cheap, and support themselves working from their computers as they go.  “I feel super lucky that the world is at a place where this can even be offered to me,” Thomas says.

Barbara Weibel, 66, was pushed to address her professional unrest after a dark chapter in her life. She suffered from Lyme disease. It took doctors five years to accurately diagnose her and during that time she experienced a host of physical and neurological issues, confining her on the worst days to her bed. “Those days spent flat on my back forced me to take a long, hard look at my life,” Weibel says.

“I vowed that if I could recover, I would walk away from corporate life and pursue my dream of being a travel writer and photographer.”

She had been unhappy working in the corporate world. She says she felt “trapped in the soul-sucking cycle of working incredibly long hours to earn money to buy material possessions.” Weibel had quit her job once before when she was unhappy, but after money fears crept it, she went back to another corporate job. But this time was different. “I vowed that if I could recover, I would walk away from corporate life and pursue my dream of being a travel writer and photographer,” Weibel says. Now she lives in Thailand, runs her own travel blog, and supports herself exclusively off her writing and photography.

Weibel overcame her fear of quitting her job and losing her salary, but everything didn’t fall into place right away. “My conversion from material girl to vagabond was a process that unfolded,” Weibel says. She’d wanted to travel full time but “could not envision having no home at all,” she says. So she worked up the nerve in steps. Weibel began by putting her house on the market in exchange for renting an apartment in Florida, although realizes looking back that, “When I moved to Florida I was still in fear mode to some degree.” It took two years in Florida, traveling half the time and adjusting to her new lifestyle for Weibel to work up the courage to fully commit to living on the road, but she did. At 58, Weibel gave up her apartment and sense of security and spent the next eight years living exclusively out of a suitcase.

Weibel says, “I don’t know if I would have had the courage to [leave corporate life] had I not stared death in the face. I barely scraped by,” she says, “but I loved what I was doing and that made all the difference.”  

“If you don’t continue to get out there and test yourself, you slowly die.”

Office life in general can wear on you, even when the work involves something you’re passionate about. Ward Luthi, 68 from Colorado, found himself in such a predicament. He loved nature and was lucky enough to hold positions as a city planner and park administrator, and was invited to work on the President’s Commission of the Outdoors in 1985-1986, advising congress on environmental policy.

Although his work was about nature, Luthi realized he never got to work in nature. “Having not been interested in wearing a three-piece-suit 18 hours a day,” he says, “I decided to go back into the outdoors and founded Walking the World.” Walking the World is Luthi’s adventure travel company, where he leads hiking tours in destinations across the globe for the “50 and better demographic,” as he puts it.

For Luthi, changing his career so that he spent a majority of his time outdoors, challenging himself on different hiking trails, was not only the answer to his professional unrest, it was a way to help others of his generation.

He says the physical challenges people face along his tours cause stress- and sometimes that’s a good thing. “We are not made for a sedentary lifestyle. We need risk, we need to be challenged to stay mentally alert,” he says. Luthi formerly worked at Outward Bound, where part of the program’s objectives was to build self-esteem. He says his program does the same thing in his 50+ demographic. There is a point on one of his popular trips to Arches National Park in Utah where hikers reach a steep basin, miles wide. “Most people want to stay right there because it looks daunting,” Luthi says. “But we hold their hand and walk down the slopes with them. And this miraculous mental shift takes place in 70 feet. Once they understand their capabilities they want to go skydiving!”

Luthi believes in the power of nature and physical activity to keep people alive. At 68, and in excellent shape, he’s a testament to his own mantra. “If you don’t continue to get out there and test yourself, you slowly die,” Luthi says. Through Walking the World, Luthi tries to help his contemporaries understand that mindset. Participants come on a walking tour, push themselves, and leave reminded of how capable they are- regardless of age.

Luthi feels fortunate that he followed his own advice all those years ago, and pushed himself to leave corporate life.  Starting his own organization, getting out in nature, helping others, and making a living off it to boot is something Luthi feels plainly about: “It helps me in my relationship to other people and the world,” he says, “but it also helps me feel alive, fully alive.”

About the Writer

Franny Donington-Ayad is a freelance journalist who wants to create a body of writing that resonates with people. That, and stop being a waitress, feel comfortable in her own body, take her mother to Kenya (to see giraffes),  own a beach house, fill that beach house with a family, live in another country for a few years,  meet Keanu Reeves (maybe get a cup of coffee with him), and feel more comfortable not knowing what the future holds.

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