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How remote can you go?

Female traveler holding a laptop while gazing at the ocean

By Elizabeth Exline

At a glance

  • Bleisure travel refers to working vacations when employees extend their stay and work remotely before or after their getaway.
  • An increasing number of Americans are exploring opportunities to relocate to countries, primarily in Europe, while working remotely.
  • Employees should check their company's policy on work and travel programs as well as federal and state tax liabilities when considering a relocation or extended vacation.
  • For more career advice, subscribe to the weekly University of Phoenix Career With Confidence™ newsletter on LinkedIn!

Bennifer. Brangelina. Bleisure.

Okay, so maybe the first two have slightly more name recognition than the last. But considering that the third portmanteau refers to the increasingly popular practice of blending work and leisure travel, bleisure may just have more staying power. (Sorry, Bennifer!) And it spells change for the way we both work and travel.

Blurred boundaries

The idea of working while on vacation is nothing new. The two are common if undesirable bedfellows since there are never enough hours in a workweek. Who hasn’t, after all, felt the need for a vacation after a vacation when hundreds of unread emails and missed updates are waiting for you upon your return?

Bleisure travel, however, just might be the answer. Tapping into the sense of opportunity rather than obligation, bleisure travel lets you capitalize on what many of us do already: mix time on with time off. If you aren’t otherwise able to travel, or if you can’t travel for as long as you’d like, bleisure travel lets you work around your vacation.

That means you can stay longer, travel farther or simply travel more frequently. According to a Deloitte study cited in, those who fit work into their trips will travel twice as often as those who head out of town merely for pleasure. The majority of these so-called “laptop luggers” will extend their trips by three to six days, although some might stay on for several weeks.

When done well, bleisure travel affords the best of both worlds: inspiration from working someplace new as well as R&R. When done wrong, you favor one to the detriment of the other.

Interestingly, bleisure travel may also serve as a gateway to another related trend: relocating abroad. According to a separate article on, inflation, political discord and soaring house prices have led to record numbers of Americans relocating to Europe. Some of the continent’s most popular travel destinations, including Greece, Portugal, Italy and Spain, are experiencing the biggest spikes in American expats who are taking advantage of the affordable housing and currency parity to call Europe home.

But before you book ...

If all of this sounds too good to be true, Lisa Severy is inclined to agree with you. Severy is a career advisor at University of Phoenix who has seen this play out professionally and personally. 

Lisa Severy

“It seems so simple, but it’s really not.”

“I think people would be somewhat surprised by how many things are actually location specific, even if you work remotely.”

Lisa Severy, UOPX career advisor

“It seems so simple, but it’s really not.”

She cites as an example her own sister who, as a history professor, wanted to relocate to Rome for a year. Her sister’s husband was onboard until he discovered that, as a financial planner, he couldn’t work for his company if he lived abroad for an entire year.

Finance isn’t the only industry hamstringed by restrictions. Severy is a mental health counselor as well as a career advisor, and she can’t treat anyone outside of the state where she lives and is licensed, not even virtually. And if she travels across state lines, she can’t practice unless she’s licensed there.

Living and working beyond your home state, in other words, isn’t always a matter of landing a remote job and taking off. But if you do want to travel while working remotely, Severy has some advice.

Steps to make it happen

Whether you’re looking to travel across the country or the ocean while holding down a job, Severy says success usually boils down to trust and transparency. The more you involve your manager in the decision-making process, and the more upfront you are about the challenges and opportunities, the better your chances are for getting permission and making it work.

Here's how to do it.

Do your homework

The first step is always research. Check with your company’s human resources department to see what travel programs and policies are in place regarding remote work and working vacations.

For tax reasons, some U.S. companies don’t allow their employees to work while traveling abroad. Other times, it’s simply a matter of discussing an extended vacation with your manager. Either way, this is one of those situations when it’s better to ask permission than forgiveness. Few trips are worth losing your job over.

If you get the greenlight from your employer, you’ll also need to look into what your tax liability is. Some states require taxes if you live there while working. You can research this on your own, but it’s also a good idea to talk with a professional tax planner.

There are other boxes to check during the research phase, too. Does your healthcare policy cover you if you’re traveling for an extended period of time, or do you need a specific travel program health insurance? What about if you leave the country? How about your dental insurance?

Then, of course, there are the day-to-day considerations to take into account. Will there be a time difference you’ll need to work around for meetings? Does your company have a slow time of year when it would be better to travel? Summer and the winter holiday season, for example, may be better times to try a working vacation or relocation than in fall or spring.

Create a win-win proposal

If all the stars (and policies) align, it’s time to have the conversation with your manager. “I think there are some people who are skeptical that, if you’re working from home, you’re actually working,” Severy notes. “Even more so if you say, ‘I’m going to be doing it from coastal Spain.’”

That’s why it’s important to present the idea with all the contingencies covered. In addition to explaining how you’d accommodate any time difference, explore new goals you could achieve, like meeting with colleagues, securing new clients or contracts in a different location, or even building your own intercultural competency.

As with a resumé or job interview, you’ll want to offer some value with your request. “If you’ve given [your company] some good reasons why this would be a win-win for you and for the organization, that will make it even easier on [your manager] to make the same argument [up the chain of command].”

Clear it with your coworkers

To be fair, your coworkers don’t have much say in your ultimate decision. But it won’t help your case if your colleagues feel like they’ll have to pick up your slack while you’re cavorting in the Caribbean.  

So, Severy recommends initiating an honest conversation built on those two familiar pillars: trust and transparency. If there’s any discontent brewing, ask your colleagues to share it and then brainstorm solutions together.

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Can you hack it?

Perhaps the biggest consideration when contemplating a working vacation or relocation is … you. Are you self-disciplined or easily distracted? Could you strike the right balance between enjoying your vacation or temporary new home and meeting your deadlines?

Even if you can, do you want to? As Severy points out, a far greater problem in the U.S. is all the unused vacation time employees never take. Yes, it can be nice to have it all when it comes to travel and career. But it can also be nice — and mentally healthy — to keep some parts of your life compartmentalized.

“If you want to go somewhere for a month, take vacation and go,” Severy says. “Use the time off that you have.”

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