Work From…Anywhere? Tips From Travellers Who Do ‘Workcations’ Right
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Work From…Anywhere? Tips From Travellers Who Do ‘Workcations’ Right

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 travelling in the first place.

By JEN ROSE SMITH
Fri, Sep 15, 2023 8:49amGrey Clock 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 travellers 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.

Get in the (time) zone

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.”

Make space

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 travelers 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 travellers 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.

Log off

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 travellers 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.”

The Wall Street Journal is not compensated by retailers listed in its articles as outlets for products. Listed retailers frequently are not the sole retail outlets.



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The Rise of Million-Dollar Companies With Just One Employee

Artificial intelligence is making it easier than ever to build a business without building a team. As AI takes over coding, customer support, marketing, administration, and other day-to-day tasks, a growing number of solo founders are scaling startups to millions in revenue with few—or even no—employees. While the trend is lowering barriers to entrepreneurship, it is also reshaping hiring, raising questions about the future of work and how businesses will grow in the AI era.

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Ben Broca launched a company last December that offers AI tools to entrepreneurs. He’s already added 10,000 paying customers and is on track to bring in $10 million in revenue this year.

One thing he hasn’t added: any other employees.

The 40-year-old is part of a class of entrepreneurs who are launching, and then often running, new companies on their own. Artificial intelligence tools answer Broca’s emails, help write and debug code, field requests from customers, sign up new subscribers and grant refunds when issues arise.

Broca relishes his ability to make whatever decisions he wants on his own, often from his sun-drenched Sausalito, Calif., living room. “I think compromises make lukewarm results,” he said.

Once upon a time, running a business of a certain size required a team. AI is turning that assumption upside down, and more aspiring entrepreneurs are going it alone.

Ben Broca sitting in his home office.
Tech has seen an explosion of solo founders in the past year. Broca said he likes being able to work at his own speed, unencumbered by a team. Jonah Reenders for WSJ

An analysis by the payments company Stripe shows there are thousands of solo operators on the company’s platform that are generating over $1 million in revenue, with their ranks doubling between 2023 and 2025. The number of solo operators crossing the $10 million threshold nearly tripled in that same span.

In the past, people without business contacts or particular savvy might not have known how to get their ideas off the ground, said Ernie Tedeschi, Stripe’s chief economist. “Now, AI can be a built-in business partner,” he said.

AI’s ability to handle various administrative tasks makes it potentially useful for launching solo businesses in many fields. But the technology’s ability to also handle key tasks in tech, like coding, make that field a particular hot spot.

Analyzing Census Bureau data, Bank of America Institute economist Taylor Bowley found that among all industries, new business applications in the information sector have seen the biggest percentage increase—nearly 45%—over the past year. At the same time, the rate of information-sector applicants saying they plan to hire workers has experienced the sharpest decline of any measured industry.

This Census dataset doesn’t track solo-operated businesses. But the numbers broadly show—in tech and beyond—that applications are flat among businesses likely to hire workers, but generally rising elsewhere. Economists say that’s a strong sign that solo operators are on the upswing.

“The bar for getting started has never been lower,” said Julian Weisser, who runs a San Francisco-based accelerator for solo founders working in tech. The accelerator—which offers founders seed money and mentorship in exchange for an equity stake—attracted 4,500 applicants for 10 slots made available in its most recent cycle, nearly five times the number it drew when it launched last May.

Going it alone with AI can still be surprisingly expensive. Broca said he was losing money on many customers’ accounts while paying to access Anthropic’s Claude to run his clients’ requests—that AI company, as well as others, charges based on usage. He has since switched to free open-source AI models from China.

Broca said he has raised $30 million from investors and, at the same time, has saved millions in salary since he hasn’t needed a team of software engineers.

Another risk: If it’s easy for one entrepreneur to launch an AI-assisted business, copying them can be easy, too. This creates anxiety for founders like Troy Johnston, who runs an AI-assisted business alone in Orlando, Fla.

“Everybody has the sword and we all have the ability to unsheathe Excalibur now,” said Johnston, 40, who used AI to code an app that helps people get the most out of credit card benefits. The company makes around $3,000 a month in profit, with no employees, and is continuing to grow.

Headshot of Troy Johnston.
Troy Johnston said AI’s power and ease of use is an incredible boon for entrepreneurs like him—and also a double-edged sword. Luann Koerper

What one-person businesses will mean for the labor market remains to be seen. Polling has shown Americans are worried that AI will replace jobs, and top economists are wrestling with that possibility, too. But AI is also creating lots of new jobs, and the go-it-alone entrepreneurs show how the technology can both open doors and limit employment opportunities.

“If everyone’s hiring less, but you get four times more firms, what does that do to head count?” said Rembrand Koning, an associate professor at Harvard Business School who studies entrepreneurship. He co-authored a recent study that found that among 50,000 startups the researchers examined, those focused on AI tended to operate with 25% fewer employees.

Koning also believes a soft hiring environment that’s left some people mired in long job searches has encouraged more to try their hand at launching businesses.

Some founders cite different motives. “It’s a perfect storm of post-pandemic burnout and a re-evaluation of one’s priorities, and also booming AI and a sense of what’s possible,” said Samir Ahmad, 39, who lives in Breinigsville, Pa.

Two years ago, Ahmad decided to leave the corporate job he had worked at Verizon for almost two decades to start a solo coaching and consulting business. He had been seeing social-media posts touting the ease and virtues of AI, which he used to chart a business plan and help with marketing. “It was like my chief of staff, a second in command,” he said.

The business ultimately petered out within months, though, and Ahmad is now back to a full-time corporate role with a utility company.

For Claire Vo, 41, AI helped her turn a passing impulse into a business. She was working full-time as a tech executive when she tapped AI in late 2023 to help code an app that would help her manage documentation and design for new products, with customers ranging from financial services to healthcare firms.

“I was copying and pasting from ChatGPT,” said Vo, who lives in San Francisco.

Claire Vo smiling into the camera while recording a podcast.
Claire Vo used AI to code an app that’s on track to make seven figures in profit this year. Claire Vo

She put the app online for $1 a month, and within weeks people downloaded it thousands of times. Nearly three years later, Vo’s company—which she ran solo for nine months before hiring an engineer—now has 100,000 users and is on track to make seven figures in profit this year. AI handles the company’s marketing, sales and customer support.

While AI is a shortcut, Vo said her network and credibility in the industry were key. “I think people over-index on how easy AI is and under-index on how much I did to get to this point,” she said.

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