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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As AI productivity trackers reshape workplace evaluations, employees are learning how to manage calendars, activity levels and AI usage to ensure their contributions are recognized.
4 min
What’s more important than being a good employee right now? Looking like a good employee in the eyes of AI productivity trackers that more managers are using to evaluate their teams.
Employee-monitoring systems are especially popular at tech companies and are also used by other white-collar firms that want to probe how people spend company time. The scary thing: You might not even know you’re being watched because many states don’t require disclosure.
Metrics can include performance data that is undoubtedly relevant, such as sales results. But it also can employ dubious proxies like keyboard strokes and how often your computer screen goes into sleep mode.
We generally accepted, or at least understood, heightened surveillance during the work-from-home era. Back then it seemed reasonable for bosses to keep tabs on employees they couldn’t see.
Yet the oversight has only escalated, and tensions are rising, too.
A group of former Meta Platforms employees alleges in a lawsuit that the company used a “constellation of internal artificial-intelligence systems” when it began laying off about 10% of its workforce in May. Meta says humans make termination calls.
However that case shakes out, a couple of things are clear. Companies eager to gauge which employees are locked in now have sophisticated AI monitoring systems at their disposal. And they believe they have leverage in a tepid labor market.
So while we may chafe at having our worth reduced to numbers on the boss’s productivity dashboard, we have to play the game as it’s being played. Here are some tips, based on conversations with people who make employee monitoring systems—and others who game the systems.
Calendar integration is one way that productivity trackers have gotten more advanced and, ostensibly, fairer.
Let’s say you make an old-fashioned phone call or attend an in-person meeting. Your Outlook or Slack status may switch to “away,” making you appear as inactive as if you were taking an extended coffee break.
Employee monitors like one made by a company called Insightful cross-check your online status with your calendar to see whether there is a valid reason for your apparent inactivity. If that call or meeting is on your schedule, then the system will recognize that you are busy offline. If nothing is on the books, it could look like you’re slacking off.
Let’s not go any further without addressing the underlying question: How much downtime is permissible during the workday? After all, people have been scared to let managers see anything non-work-related on their screens since personal computers first arrived in offices.
No one knows this better than Roger Wagner, who is widely credited with creating the first “boss button” in the early 1980s. He designed a keyboard shortcut to instantly display a spreadsheet if the boss walked by your cubicle while you were playing a computer game. Boss buttons have been features of countless diversions since. (I confess to using one built into a March Madness streaming app.)
Wagner, the founder of computer-education company 1010 Technologies, says his original design was a joke—more of a commentary on overbearing managers than a cover for lazy employees. Good bosses understand workers need mental breaks throughout the day, he says.
This matches what I heard from Insightful Chief Executive Ivan Petrovic. He says customers that use his company’s workforce-management platform don’t expect employees to stay on task 100% of the time.
“On average companies are aiming for 60% to 80% of your time being utilized for work during the day,” he says.
Go ahead and exhale. It’s probably OK to watch an occasional YouTube video at your desk.
And if you’re going to artificially inflate your activity level, be careful. Hitting 90% could look suspicious.
So don’t leave your mouse jiggler on all day. Choose the right one if you must resort to shenanigans.
There are lots of software applications that mimic the movements of a computer mouse, so you can appear to be working while away from your desk. There are also devices that plug into computer ports and do the same thing.
Corporate cybersecurity systems increasingly block these apps and devices, and productivity trackers claim to be able to detect them. But some workers swear by mouse docks, like one made by Tech8 USA, that keep cursors moving. The company originally made mouse-moving software but now focuses on physical jigglers.
“People are drawn to mechanical solutions because they’re so simple and don’t require software,” says Tech8 Marketing Director Sam Matthews. “As monitoring technology becomes more sophisticated, that distinction has become even more relevant.”
Another popular metric for employee-monitoring systems is AI usage. Companies want to know who is embracing new tools, and it can be tempting to think more is better.
“There’s a performative aspect where employees overblow their usage of AI so that they appear relevant in the organization,” says Andrea Derler, principal researcher at Visier, which helps companies track and analyze employee work habits.
In a recent Visier survey of 1,000 U.S. workers, 48% admitted to exaggerating their AI usage.
This is already an outdated strategy. Using AI for everything used to score points for experimentation. Now it can seem wasteful because many companies are watching AI token spending more carefully.
Look, productivity theater has always been part of work. Most of us aren’t trying to cheat the system, but expectations are changing so quickly that we need to be savvy about what the latest employee trackers are looking for.
Sometimes it takes a little gamesmanship to get full credit for our contributions.
