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Remote Jobs Let Older Adults ‘Work from Roam’

How more Americans are using flexible jobs to travel, explore


spinner image siobhan farr working from a restaurant in lisbon portugal and walking through the city
Siobhan Farr, 66 – founder of Digital Nomads Beyond 50
IGOR MARTINS

In 2021, roughly a year after corporate America sent so many employees home with laptops due to the COVID-19 pandemic, the burning question was whether remote work would become permanent. We have our answer. As we approach the four-year anniversary of the pandemic’s start, about 40 percent of American adults still log in from afar, either full-time or in hybrid work arrangements, according to WFH Research. And the share of remote workers is expected to increase, says hiring site Upwork.

We’re entering the next stage of this shift, in which remote workers increasingly explore their new geographical freedom. Many are discovering that “work from home” doesn’t need to be taken so literally and they can travel without using up vacation days.

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“What the pandemic made me realize was that older adults were concerned about the quality of their personal lives,” says Siobhan Farr, 66, founder of Digital Nomads Beyond 50, a networking group that has grown to 2,150 members. “What we have left of life is too short to be spent going into the office. People thought they’d have to wait until retirement to travel, but they don’t.”

Though Farr took her experience to the extreme by selling off her belongings and traveling internationally full-time while still working, her Digital Nomads group includes people interested in all levels of this lifestyle.

“You don’t have to be a full-time nomad,” says Farr, who has visited 15 countries in nine months. “You can explore for three or four months and be otherwise home-based.”

Here is how some older workers are taking advantage of their newfound ability to roam.

Ben Miller, 50

spinner image benjamin miller in two photos one on his boat with family and another in his home office in coeur dalene idaho
Benjamin Miller, his wife Carrie and daughter Lily and their Boston Terrier Luna enjoy spending time together enjoying their boat on Lake Coeur D'Alene, Idaho. A financial manager, he works from his home office.
Angie Smith

Financial planner

Home base: Coeur d’Alene, Idaho

Miller serves his clients’ needs from his cabin in the woods. Or floating on a boat. Or from a rental house.

This wasn’t always the case: “I loved going into the office. I had a ‘you must be at work or you will fail’ mentality. I was stuck on that for a long time.”

But when face-to-face meetings dwindled and his office rent increased during the pandemic, Miller built an office on his Idaho property. That led to working elsewhere too.: “It was an organic transition. You almost have to retrain yourself that you can work from the hotel room and field calls from my stepdaughter’s gymnastics meet in Montana.” 

During a work-travel trip, Miller generally completes a big chunk of duties in the morning, carves out afternoon free time, then clocks back in at the end of the day.

“I don’t want to work for 15 minutes here and 27 minutes there,” he says. “I’d rather get it done, check the box and know that right before the market closes, I’m going to make sure there’s nothing on fire.” Says his wife, Carrie: “The flexibility is the biggest perk. If my family is having a birthday party [in Boise],​ it's never ‘Let me see if I can get time off.’ ”

Marsha Stevenson, 54

Graphic designer

Home base: North Hills, California

Working remotely means Stevenson can more easily split her time between two important people in her life: her husband and her 86-year-old mother. As a caregiver, she spends the majority of her time with her mom in North Hills rather than with her husband in Culver City, California. Although the distance between those two communities is only about 20 miles, she finds it easier to work much of the time from her mother’s house: “I have to consider Los Angeles traffic.” ​

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Stevenson has a supportive supervisor and coworkers, but balancing remote work with caregiving and travel requires transparency: “Giving a heads-up when I won’t be available for an hour or so has helped manage expectations. Be good at communicating what you’re doing, and do what you can to make up for time away. With remote work, employers know they have a dedicated worker who can focus more on their job, knowing their loved ones are still well cared for. I am fortunate to have a really good team to work with. They know that when I can, I will go that extra mile to accommodate a rush job and turn stuff around as fast as I can. It’s life.”

Bob Larson, 59

spinner image tami and bob larson in alaska
Tamara and Robert Larson stand near their property in Kenai, Alaska. Robert works remotely, so the couple are able to work on renovating a foreclosure in Alaska and also will spend most of the year traveling.
ASH ADAMS

Technology consultant

Home base: Folsom, California

Larson adopted a work-while-traveling lifestyle with his wife, Tami, after starting a remote job during the pandemic.

“Tami’s biggest concern is that she wants to be close to family,” says Larson, whose four adult children live in Utah and the Washington, D.C., area. “We want to visit with them and nurture those relationships.” 

The couple make frequent treks to their timeshare in the Utah mountains and recently took two family jaunts to Hawai‘i. But they also travel abroad, and their children, friends and other family often visit on those trips. 

International travel does cause some time-zone issues.

“I do have to get up at 3 a.m. and have a meeting some days. It’s been an adjustment to break up the workday,” he says. “It’s a sacrifice, but you have to be able to make sacrifices for this kind of lifestyle. The benefits outweigh the drawbacks.” 

Larson was never a fan of being stuck in an office, so he considers this the ideal scenario: “Gone are the days where you have to sit at your desk for eight hours and wait for someone to walk in the door. It’s very different in today’s environment. You’re just a phone call away.”

Jean Dibble, 61

spinner image jean dibble pictured at her home office and in her home art studio
Jean Dibble works from her home office in Spokane, Washington. She also enjoys drawing and painting from a room that she has turned into her art studio.
Angie Smith

Translator and English as a Second ​Language (ESL) teacher

Home base: Spokane, Washington

Dibble lived in China, working as an ESL teacher before the pandemic. But she happened to be visiting her mother in Yakima, Washington, when the world shut down. And so her job became remote. As the world reopened, it dawned on her that she could travel while working: “It’s not like I planned this, but COVID gave it to me.”

Dibble started by staying in Mexico a few times, then explored Washington state via Airbnb rentals before settling in Spokane: “Because of time zones with China, I would work weird hours, mostly at night. So I would get up, go out and explore, walk and go look at things and meet friends. I’d make sure I was home by 4 p.m. to get my ducks in a row.” 

Dibble added another remote job doing English-to-Spanish translation work for a magazine, for which she sets her own schedule. This flexibility has allowed her to visit her mother, go camping in Washington’s Hoh Rain Forest — with a pit stop in civilization to work via Wi-Fi — and see a new baby in her extended family. 

“Back in the day, I’d count my vacation days and be waiting, waiting, waiting to do something for me,” she says. “But now I can do that whenever I want. I feel like I can do this work into the sunset. I’m not counting down my days until retirement.” 

Balancing Work and Travel: ​The emerging rules of the road

*Regular check-ins are key. Plan times — daily, weekly or monthly — to touch base with bosses and coworkers to ensure that work is on track. “I have to make all of my daily calls, no matter where in the world I am,” Larson says. Be sure to track and share your progress on projects to demonstrate your work ethic and overcome any perceptions that you’re not engaged. With such check-ins, Larson notes, most people often won’t notice that you’re in another location

Stay connected. “Surround yourself with technology, even if you don’t wind up using it,” Miller says. “We get to a place and immediately log on to the internet on all devices, so we’re ready to go.”

Make work a priority.  “Change locations on the weekends,” rather than during the week, Larson says. “Make it easy for your employer to allow you to travel by having few disruptions. Work is the goose that laid the golden egg. Don’t kill the goose.”

Create a schedule. Choose the times you will and won’t work. “If you’re going to be at work mentally the entire time on a trip, what’s the point?” Miller says. “You really do have to say, ‘At this hour, I am going to shut off and enjoy being away from my home and enjoy travel.’ ”

Trust yourself. “Don’t hold back because you don’t feel like a technology expert,” Dibble says. “At first, I didn’t even know how to set up a Zoom meeting. But you figure it out. If you don’t know all the answers, don’t let that stop you.”

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