On this month’s Dear Fodor’s, we answer a question most remote workers have probably pondered at one point in time: do you really have to tell your boss if you’re working abroad?
Dear Fodor’s, I work fully remote and have a pretty flexible schedule. Because of that, I’m thinking I should switch things up and go work remotely abroad for a week or two in Mexico. The thing is, I don’t want to ask my boss permission to go. I’m afraid that she will think my working at a beachside town will mean I’m “on vacation mode” and therefore not taking my work seriously. I could probably get away with not saying anything to my boss, using blurred backgrounds on Zoom calls and such, but I wonder if that could get me in trouble. Do I have to tell my boss I’m working abroad or can I just go?
Iam sure our American workers—many of whom are only given a measly number of paid vacation days—can sympathize with your desire to take a “workcation.” If you are fulfilling all your job duties but get to enjoy the destination during your downtime, then everyone wins, right? How problematic can it be? Unfortunately, this is one of those situations where the ethical—not to mention legal—implications are more complicated than they seem.
The Legal Pitfalls of Working on Vacation
In most cases, when you enter a country on a tourist visa, you’re declaring that you will be there for leisure purposes only. Walk into any cafe in a place like Bali or Mexico City, however, and you’ll find countless tourists on laptops. Whether they realize it or not, these travelers might be flouting the terms of their entry. While many countries have introduced digital nomad visas—and some even permit temporary remote work for visitors—the majority strictly prohibit tourists from working in any capacity.
Continue Reading Article After Our Video
Recommended Fodor’s Video
“Most travellers think that if they get paid by an employer in the United States, they are protected from immigration attention in a foreign country. In most jurisdictions, that is not the case,” says New York-based attorney Robert Tsigler, noting that some countries impose three to ten years of removal and entry banning for tourist visa violations. “Immigration enforcement doesn’t recognize the difference between coding and consulting or having video chats. If you are doing paid work in a foreign territory, you are subject to the law,” he adds.
And, in case you’re thinking, “but it’s only a couple of weeks,” Tsigler stresses that duration is irrelevant. “Immigration enforcement agencies view unauthorized labor as an immediate visa violation regardless of a brief duration, like a week or two,” he says. “A short timeline does not shield a traveler from immediate deportation orders or subsequent visa denials if customs officers discover unapproved electronic telecommuting.”
Additionally, it’s not just the worker who will be impacted, says Divij Kishore, founding attorney of Flagship Law; employers can run into legal trouble too. “Many U.S. employers require employees to disclose where they are working. Those policies are not necessarily about productivity. They often exist because the employer’s tax, insurance, cybersecurity, privacy, regulatory, and compliance obligations can change depending on where an employee is physically located.
Although it’s admittedly pretty rare for customs and immigration to enforce these laws, low odds of being caught shouldn’t be an excuse to go for it. “Remote work has convinced many people that geography no longer matters. The law has not necessarily reached the same conclusion,” adds Kishore.
How to Negotiate a Workcation With Your Employer
If you’ve done your research and found a destination that permits short-term work on a tourist visa or offers an easily attainable digital nomad visa, I’d strongly suggest an honest conversation with your boss as the next step.
Marisa Meddin, co-founder of Beach Commute, a company that specializes in helping people find remote work opportunities, stresses that for short-term trips abroad, “the bigger practical concern often becomes trust rather than taxes.”
“We’ve seen plenty of remote workers travel without explicitly discussing every trip with their employer, but this usually leads to more stress, as you may spend the trip wondering whether you’re violating a policy, if someone will notice, or if you’ll have to explain yourself later,” she explains. “If you do get permission for the trip, you won’t have to spend your time worrying about getting caught. And if things go well, you’ll likely build trust that makes future trips easier to get approved, too.”
Before the conversation, set yourself up for success by assembling a well-thought-out proposal for the workcation. Imagine what your boss’s main concerns might be, from internet reliability to cyber security, and tax implications, and come up with a realistic solution for each point.
“The goal is to make it as easy as possible for them to say yes. And when you’ve already done the research and removed the friction, you’ve given them very little reason to say no,” says Kate Smith, a Remote Career Coach at The Remote Nomad, who once assisted a client with a 9-5 office job negotiate a three-month workcation in Mexico. “We mapped out where she’d be working (a co-working space with dedicated Wi-Fi), how she’d keep company data secure, and she did the research upfront to confirm that her stay wouldn’t trigger any tax obligations for her employer. Her boss said yes,” says Smith.
Aside from the logistical complexities, you explicitly named a fear that your boss will think you’re “on vacation mode” and therefore slacking off. Address this worry openly. Let her know you’re dedicated to fulfilling all your work duties regardless of location and find out which productivity indicators would make her comfortable—for example, regular Zoom check-ins or being available on Slack during work hours in your usual time zone.
To sum up, although it’s tempting to jet off without your boss’s sign-off and pretend it’s business as usual, it’s probably not worth the risk if something were to go wrong. Do your research, make your case, and enjoy an above-board workcation instead.