Back in July, Chelsea Alexander Paul and her husband, Evan, sat down in their San Francisco apartment and made a spreadsheet of places where they could live and work for the same amount of money or less.

The Pauls had lived in the city for four years and once lockdowns began, they spent months working from their one-bedroom home in the Mission District. As of now, their offices won’t reopen until August 2021, freeing them up to focus on a place with better work space and more outdoor activities.

“It felt like what we had in the city wasn’t really there anymore and isn’t going to be there for a little while,” said Ms. Paul, who is 32 and senior marketing lead at the Sheryl Sandberg & Dave Goldberg Family Foundation.

The Pauls are among the many workers experimenting with new locations and lifestyles. Such moves—even temporary ones—require attention to finances, logistics and career.

Testing out a new life elsewhere often is easier if you are working a full-time job instead of trying to land freelance projects, veteran nomads say. Sarah Solomon, who built her public-relations firm while traveling across several continents, recommends that freelancers nail down projects in advance, to build savings and have a steady stream of clients and work. She also warns that many international hostels and hotels promise reliable Wi-Fi—which turns out to be inconsistent or available only in limited areas. Check customer reviews, she advises, for the real story.

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Most people also need to claim a home base—such as the home of a parent or family member—for bank accounts and mail. Before giving up their San Francisco apartment for a series of Airbnbs, the Pauls were concerned about voting, and decided to use Ms. Paul’s parents’ home as their permanent address.

Evan and Chelsea Alexander Paul are trying out homes with better work space and areas with plenty of outdoor activities. In August, they stopped at Crater Lake National Park in Oregon.



Photo:

Evan Paul

When their lease ended in August, they put most of their things in storage. This month, the couple is renting a three-bedroom house with a yard in Tacoma, Wash. Ms. Paul asked about the desk setup before they booked, and their hosts offered a Wi-Fi speed test. Coming months will bring them, in the car they leased month-to-month, to rentals in Montana, Idaho, Utah, Arizona and California.

Ms. Paul appreciates the flexibility but finds that the Monday through Friday routine feels much the same everywhere. “I actually didn’t know how I’d adjust, but it really hasn’t been such a shift,” she says. “We designed it to work for our personalities and our day-to-day. The weekends have been a little bit more adventurous and refreshing.”

Transparency with employers and clients is essential, say people who have successfully combined remote work and travel. Ms. Solomon, who now lives in Hawaii, says she is up-front about her location and availability. Last year, when living in a camper van in New Zealand for six weeks, she would rise before dawn for video conferences. “My clients knew where I was and appreciated that I was waking up at 5 a.m. to be on the weekly call,” she says.

Ms. Solomon, 28, says she tries to maintain ample savings to deal with unexpected costs. She pays for her own health insurance and at times has chosen a plan that covers her in the U.S. and internationally. This, she notes, can be a big expense that anyone considering this path should take into account. Heading off for any length of time can raise other financial issues, such as finding renters for one’s home or paying taxes in the new location.

Lockdowns spurred some to hit the road—while working. Madi Beumee, a 23-year-old actress, had just made her off-Broadway debut in “The Little Match Girl” when the pandemic hit.

Work she had lined up for the summer began to disappear and it became clear that she wouldn’t be auditioning for fall projects. Her boyfriend, Justin Boccitto, a dancer and teacher, faced similar challenges as dance studios in New York closed temporarily. The two decided to bring the tap dancing classes that Mr. Boccitto, 39, had been giving before the pandemic to places where studios had reopened.

In mid-September, they set out on a three-month cross-country drive, stopping at national parks on the way. To keep costs down, they look for free campsites. “We just didn’t want to stay and sit and be in the same mental and emotional state for four months,” says Ms. Beumee, speaking from Badlands National Park in South Dakota. She is making ends meet with freelance graphic design and social media projects.

At a rest stop in Wasta, S.D., Madi Beumee caught up with work while Justin Boccitto gave a private tap dance lesson over Zoom.



Photo:

Madi Beumee

Some adventurers have settled down, at least for the moment. Ms. Solomon says waking at 3:45 every morning is a trade-off she is willing to make to live on Maui, where she and her boyfriend, a scuba instructor, recently rented a house for six months. Most clients of her public relations business are on the U.S.’s east coast. She spent the past three years working from her laptop while exploring Central and South America, the Caribbean, Australia and New Zealand.

The major housing expense in Hawaii often is electricity, Ms. Solomon says, but theirs is included in the lease. The cost of living is comparable to other places she has lived in the U.S., such as New York City and Asheville, N.C., she says. And Hawaii offers free activities such as swimming and hiking.

Sarah Solomon watched the sun rise at Haleakala National Park on Maui in September.



Photo:

Sarah Solomon

Early this year, Ms. Solomon and her boyfriend were living and working on Heron Island, in Australia. They returned to the U.S. and spent several months near his parents in North Carolina before relocating to Hawaii in July. Ms. Solomon had lived on Kauai and Maui in 2018 and 2019 and wanted to return. “We had always planned on moving back to Hawaii,” Ms. Solomon says. “But we didn’t expect it to happen so quickly.”

Early this year, Daisey Traynham and her husband, Britt, a photographer and music producer, arrived in Da Nang, Vietnam, and planned to stay for a month before traveling throughout southeast Asia.

When coronavirus hit, they signed a six-month lease on an apartment. “Covid happened and it was like musical chairs,” says Ms. Traynham, 47. “The music stopped and you just had to sit and stay still. This is really the longest we’ve sat still in years.”

They have spent much of the past 16 years stopping in places just long enough to get to know them. Ms. Traynham, who has worked for software developer Art+Logic for 20 years, says she gets restless in the same place too long. Most years they divide their time among Asia, Berlin—where they own an apartment—and the U.S. Pacific Northwest, where they keep a camper van. To keep east coast hours, Ms. Traynham works from 9 p.m. to 5 a.m. in Vietnam. She and her husband have acquired a motorbike and kitchen goods in Da Nang but Ms. Traynham sees travel in their future.

“My mom asked me, ‘Honey, you’re going to come home, right?’ I said, ‘I am home!’,” she says. “It’s weird—home is kind of just where you hang your hat or where your Wi-Fi connects.”

Daisey and Britt Traynham in Vietnam this year before the Covid lockdown.



Photo:

Daisey Traynham

Write to Kathryn Dill at kathryn.dill@wsj.com

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