Officing from Palm Springs for a few weeks? Want to workcation abroad this summer? Be sure to clear it with your employer. The ease at which we can all work while traveling puts data at risk, can lead to complicated tax and legal issues, and may even be terrible for your health. In fact, your best bet—and sometimes the safest and most ideal solution for your employer—may be to take that time off from work. You know, actual vacation time rather than having to work while traveling. Imagine that!
The pandemic transformed our ideas of where a workplace can be and what it looks like. Many of us got really good at juggling work and life, even when we didn’t think we could. We got so good at it that we began to wonder why our employers need to know WHERE we’re working from at all, as long as we’re working.
Well… there are several good reasons.
When you work while traveling, you become a worker IN the location at which you’re working. That’s why you need to know how to ask your boss to work remotely because that location may have an entirely different set of employment, business, and tax laws than those that govern your usual workplace.
“Some states have a rule that employees have to be in a location for 30 days or more before they pay taxes there, whereas in others it’s only a matter of a few days. And if employees go outside the country, that opens up another can of worms with regard to international work authorization and more,” explains SHRM’s Kathryn Mayer.
Doing work while traveling can be a big, hairy tax issue for your employer–and you. It may also violate immigration and other workplace laws. And becoming an independent contractor to work while traveling nonstop is not an iron-clad solution. Why? The definition of an independent contractor and the rules for these individuals also vary significantly by jurisdiction. If your work relationship violates the classification of an independent contractor in a city, state, or country where you are working, you could jeopardize your employer’s ability to do business in that jurisdiction in the future. That’s a big deal. Learn how to ask your boss to work remotely so there won’t be any issues.
Not telling your employer you plan to work while traveling can make them vulnerable to these issues and more. And when it comes to noncompliance, who do you think the IRS and other workplace authorities will go after, you or them? (Hint: It’s the employer.)
So, when your employer insists you don’t work while on a travel, they’re looking out for you AND themselves. And listen, taking a break is good for you. American workers notoriously take fewer vacations, work longer days, and even retire later than their foreign counterparts. A 2019 study found a record 768 million vacation days went unused, with 55% of workers reporting they didn’t take all the paid time off their job offered. That behavior—including planning to work while traveling when you could be taking time off—can have profound health implications. In 2021, the World Health Organization reported that long working hours were linked to about 745,000 annual deaths from stroke and heart disease, a nearly 30% increase since 2000 in deaths related to overworking.
Then there are the data security risks of checking your email and conducting official business while traveling. Reasons why you need to know how to ask your boss to work remotely. While cybersecurity and physical security of equipment and devices are issues anywhere you work, some countries, public areas, and lodging/long-term rentals are more vulnerable to attacks than others. You’ll want to give your employer a heads-up when you work while traveling for that reason, too.
So, the next time you want to balance spreadsheets in Belize, consider opening a dialog with your employer about the pros and cons of doing so. Working while traveling may be a bad idea for you both.
