Want to make your time off go further? Take advantage of remote work to set up in a holiday location for a week, even a month. The risk: missing the point of traveling in the first place.
3 min
ASHLEY SCHWARTAU escaped to a Mexican beach town just two weeks after starting a new job for a Chicago-based insurance company. It’s not that Schwartau, 38, is a late-blooming spring breaker. She and her husband both work remotely, so when winter arrived at home in Nashville, Tenn., the pair decided to clock in from a vacation rental with a pool in Playa del Carmen.
For the next four weeks, the couple took calls from their temporary home, while their 4-year-old son attended a bilingual preschool whose $350 monthly tuition would be implausible back in Nashville. After hours, the trio played at the nearby beach, lounged poolside or grazed at neighbourhood taco stands. Following a weeklong-vacation chaser at month’s end, they returned to Tennessee restored. “It’s hard for working parents to truly find moments of relaxation, and that was one of the most relaxing trips we’ve ever taken,” said Schwartau, who documented the trip on her blog to inspire others looking to expand their own definitions of remote work.
Unlike some full-time “digital nomads”—who skew young, male and child-free—Schwartau has no plans to permanently swap home life for stints in Lisbon or Bali. Instead, Schwartau used her hybrid “workcation” to capitalise on a remote-friendly job and temporarily set up shop away from home’s routines and responsibilities.
The trip also let her save some paid time off while still traveling, a strategy that appeals to workers in the U.S., where the average private-sector job affords just 11 days off after a year. With employers increasingly offering flexible work options, workcations seem to be a pandemic-accelerated trend with staying power. A 2023 study by Deloitte showed that one in five travelers planned to do some work on their primary summer trips, with many using flexible policies to eke out additional time away.
Still, obstacles abound. Jet lag can sap work output, sand will destroy your computer and dutifully clocking hours a block from a beach invites intense FOMO. It takes finesse to make workcations work—here’s how to pull one off.
Going too far afield—or heading in the wrong direction—can tug routines out of alignment. Dan Hammel of Benicia, Calif., works for a tech concern that follows Central time and offers staffers two annual work-from-anywhere weeks. Last fall, Hammel spent one off-kilter week working from the Italian city of Bologna. “My hours in Europe were probably about 4 p.m. to midnight,” he said of the need to align with his stateside colleagues’ workdays. After days spent touring nearby Modena and Parma with his wife, Hammel found the schedule challenging. “I like to be in bed around 10,” said Hammel, 45.
To avoid red-eye marathons, follow your natural sleep pattern to the optimal time zone. For Hammel, that meant Maui, where he worked remotely in May. “I would get up at 5 a.m. and would be done around noon,” he said. “We would have the whole rest of the day to nap, relax for a little bit after my workday, hit the beach, go to dinner.”
Remote work might conjure Instagram shots of laptops lolling on beach chairs, but such scenes don’t translate to meaningful productivity. Deloitte found that more than half of all travellers look for work-friendly spaces when booking accommodation. William DeSousa, 73, a public-relations professional from Osterville, Mass., craves more space than hotel rooms offer: He’s a villa guy.
For 16 years, he’s spent a month working from Greece with his husband and has learned that walls do wonders. “We both need to be on phones, or be on Zoom calls,” he said. “I think separate workspaces work best for couples.” This year, the pair will enjoy the beach-and-taverna circuit while clocking in from villas in Santorini and Crete.
Other travelers opt for hotels—such as Mama Shelter Shoreditch London and the Hoxton Chicago—with dedicated co-working areas and brisk internet. Whatever you decide, ask for bandwidth details before booking: The website Global Nomad Guide, which advises remote workers, recommends download speeds of at least 50 Mbps.
Many remote workers are loath to shut devices down, which can lead to post-workcation regrets. Commit in advance to logging off, said Jaime Kurtz, professor of psychology at James Madison University and author of “The Happy Traveler: Unpacking the Secrets of Better Vacations.” Tell yourself, “‘I’m going to work this many hours a day, and then I will go out and take advantage of the place,’” Kurtz said. She suggested travelers seek experiences that sideline devices completely, such as riding a bike or joining a food tour.
And while remote work can help PTO go farther, don’t mistake working getaways for more truly replenishing vacations. That’s why many workcationers, including Schwartau and Hammel, follow remote stints with actual time off, using working trips as a launchpad for dedicated travel time.
Jessica de Bloom, a professor of psychology at the University of Groningen in the Netherlands, who studies the blurring frontiers between work and leisure time, considers true disconnection essential to thriving. A request for comment for this story prompted an out-of-office message, suggesting de Bloom lives by her own findings. “I am currently enjoying a vacation,” the auto-response read. “I choose not to work and check my emails, because research showed that working during holidays can be detrimental for my health.”
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Rugged coastal drives and fireside drams define a slow, indulgent journey through Scotland’s far north.
A haven for hedge-fund titans and Hollywood grandees, Greenwich is one of the world’s most expensive residential enclaves, where eye-watering prices meet unapologetic grandeur.
Their careers spanned the personal computing, internet and smartphone waves. But some older workers see AI’s arrival as the cue to exit.
4 min
Luke Michel has already lived through two technology overhauls in his career, first desktop publishing in the 1980s and online publishing later on. But AI? He’s had enough.
So when his employer, the Dana-Farber Cancer Institute, made an early-retirement offer to some staff last year, the 68-year-old content strategist decided to speed up his exit. Before, he had expected to work a couple more years.
“The time and energy you have to devote to learning a whole new vocabulary and a whole new skill set, it wasn’t worth it,” he said.
It isn’t that he’s shunning artificial intelligence—he is learning Spanish with the help of Anthropic’s Claude. But, at this point, he’s less than eager to endure all the ways the technology promises to upend work.
“I just want to use it for my own purposes and not someone else’s,” he said.
After rising for decades and then hovering around 40% in the 2010s, the share of Americans over 55 years old in the workforce has slipped to 37.2%, the lowest level in more than 20 years.
The financial cushion of rising home equity and stock-market returns is driving some of the decline, economists and retirement advisers say.
But for some older professionals, money is only part of the equation.
They say they don’t want to spend the last years of their career going through the tumult of AI adoption, which has brought new tools, new expectations and a lot of uncertainty.
Many people retire when key elements of their work lives are disrupted at once, said Robert Laura , co-founder of the Retirement Coaches Association and an expert on the psychology of retirement.
“Maybe their autonomy is being challenged or changed, their friends are leaving the workplace, or they disagree with the company’s direction,” he said.
“When two or three of these things show up, that’s when people start to opt out.”
“AI is a big one,” he adds. “It disrupts their autonomy, their professionalism.”
Michel, whose work required overseeing and strategizing on website content, has been here before.
When desktop publishing arrived in the 1980s, he was a graphic designer using triangles and rubber cement.
The internet’s arrival changed everything again. Both developments required new skills, and he was energized by the challenge of learning alongside colleagues and peers.
It felt different this time around. “Your battery doesn’t hold a charge as long as it used to,” he said.
He would rather spend his energy volunteering, making art, going to operas and chairing the Council on Aging in North Andover, Mass., where he lives.
In an AARP survey last summer of 5,000 people 50 and over, 25% of those who planned to retire sooner than expected counted work stress and burnout as factors.
About half of those retired said they had left work at least partly because they had the financial security to do so.
In general, older Americans are less likely than younger counterparts to use AI, research shows.
About 30% of people from ages 30 to 49 said they used ChatGPT on the job, nearly double the share of those 50 and older, according to a 2025 Pew Research Center survey of more than 5,000 adults.
Baby boomers and members of Generation X also experienced the sharpest declines in confidence using AI technology, according to a ManpowerGroup survey of more than 13,900 workers in 19 countries.
“We as employers aren’t doing a good enough job saying (to older workers), we value the skills that you already have, so much so that we want to invest in you to help you do your job better,” says Becky Frankiewicz , ManpowerGroup’s chief strategy officer.
Jennifer Kerns’s misgivings about AI contributed to her departure last month from GitHub, where the 60-year-old worked as a program manager.
Coming from a family of artists, she said, it offends her that AI models train on the creative work of people who aren’t compensated for their intellectual property. And she worries about AI’s effect on people’s critical-thinking skills.
So she was dismayed when GitHub, a Microsoft-owned hosting service for software projects, began investing heavily in AI products and expecting employees to incorporate AI into much of their work. In employee-engagement surveys, the company had begun asking them to rate their AI usage on a scale of 1 to 5.
When it came time to write reports and reviews, colleagues would suggest that she use ChatGPT.
“I’d be like, ‘I have no idea how to use that and I have no interest in using AI to write anything for me,’” she said.
It would have been more prudent to work until she was closer to Medicare eligibility, she said. But by waiting until her children were out of college and some of her stock grants had vested, the math worked.
Her first act as a nonworking person: a solo trip to Scotland, where she took a darning workshop and learned how to repair sweaters.
“The opposite of AI,” she said.
Employers already under pressure to cut workers—such as in the tech industry—may welcome some of these retirements, said Gad Levanon , chief economist at Burning Glass Institute, which studies labor-market data.
“The more people retire, the fewer they have to let go,” he said.
Some of the savviest tech users are also balking at sticking around for the AI upheaval. Terry Grimm, who worked in IT for 40 years, retired from his senior software consultant role at 65 last May.
His firm had just been acquired by a bigger firm, which meant learning and integrating the parent company’s AI and other tech tools into his work.
Until then, Grimm expected he might work a couple more years, though he felt that he probably had enough saved to retire.
“I just got to the point where I was spending 40 hours at work and then 20 hours training and studying,” said Grimm, who has since moved with his wife from the Dallas area to a housing development on a golf course in El Dorado, Ark.
“I’m like, ‘I’ll let the younger guys do this.’”
