Friday, February 23, 2024

Want to travel while you work? 6 questions to ask your employer and yourself

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Even just daydreaming about becoming a digital nomad can open the floodgates to countless questions: When will you travel, and where? What will you pack? Where will you live, and how will you get around? And what about your job?

Some of these only you can answer; it’s your adventure, after all.

But because being a digital nomad is all about working digitally while traveling nomadically, there are some key questions that you need to ask before you can know if it’s safe to pack your bags, book that first flight, and start your new adventure.

Here are 6 questions you need to ask your employer—and yourself—before embarking on a digital nomad journey.

Approaching your employer about traveling while you work

Being a digital nomad generally requires a remote working arrangement with your employer. If you’re already remote working, discussing your digital nomad plans with your employer may be more straightforward. But if you’re not yet remote, using the right phrasing in discussing your digital nomad plans with your employer is essential.

In particular, it may be best to avoid referring to yourself as a “digital nomad” altogether. Instead, indicate that you want to explore working remotely and would like their support as you plan to travel for a specific amount of time.

A sample email you can send to your employer

Dear [Employer],

I’m writing to you today to discuss the idea of working remotely for [Company Name] while living abroad. In the past few weeks and months, I’ve become increasingly interested in moving to [destination name] in the near future, with the possibility of then moving to [Next Destination] or [Another Destination] after that.

As I would be working internationally, I expect this might require some changes to my employment contract to account for tax differences and other important details. I know our company has a [remote work policy]. I would happily work with the proper departments to make these changes happen smoothly and make any other necessary preparations.

I enjoy working at [Company Name] and would be very excited to continue my [Job Responsibilities] while working and traveling abroad. Please let me know if you have any questions I can answer or if there may be any barriers to my working internationally that I may still need to learn about.

Thank you,


What should I consider if I’m considering working remotely and traveling?

As more companies look to rebuild their company culture following recent work-from-home shifts, it’s important to consider how you can still contribute to the office while abroad. First, view the meetings and events you have in the coming months. If they require being in person to establish a clear plan, schedule the essential face-to-face time and travel.

Your employer may have to restrict or adjust some of your work once you become a digital nomad. Employers may, for example, bar digital nomads from higher-risk activities like signing contracts or joining board meetings outside the country due to security precautions. Discuss this with leadership and devise a plan to ensure any sensitive responsibilities are handed off as needed.

Does my insurance apply internationally?

Domestic US insurance plans typically don’t cover overseas care. So if your nomadic journey takes you across borders, you must obtain international medical coverage, whether a standalone plan or one wrapped into your travel insurance. You can find international medical insurance plans by searching online, but be sure to research to find the best one for you.

You can also ask your employer whether they can cover or help cover your new international health insurance. You may need to be prepared to pay for it out of pocket. It may also be best to obtain a travel insurance plan and consider your medical, natural disaster, and other emergency needs based on your travel destinations.

What if I have an IT issue abroad?

System updates that won’t install. VPN snags that won’t go away. Wi-Fi outages that drag on forever. The genuine possibility of losing or breaking your work company or phone. The list goes on and onthe same IT issues we all deal with domestically can and will happen abroad, too.

That’s why it’s essential to work with your employer and map out what support looks like while you’re traveling, and do your part to prepare yourself by researching data plans and devices that will help you stay connected.

Questions for self-reflection

Working in a new country can be an exciting adventure with new opportunities and unexpected challenges. On the other hand, being away from home for so long may be challenging, and frequent travel can sometimes be as tiring as it can be invigorating. Planning as much as possible in advance will help ensure you’re ready to take the next step while avoiding any unnecessary roadblocks or regrets.

What are the tax and legal implications?

It can be easy to forget that many legal and tax implications exist for employees and employers in remote work situations, both across US state lines and internationally. For example, you or your employer could be penalized or subject to fines from the government of the location you’re working in if the circumstances of your remote work are not compliant with their laws. And remember, if you’re a citizen of the US, you still need to file US taxes, even if you earn no money from within the US.

Be sure to research the places you plan to visit and consult your employer about whether they have policies covering you legally and from a tax perspective. Employers have different levels of flexibility concerning the legal and tax ramifications of remote work. For instance, at Wise, we can work up to 90 days a year from anywhere worldwide.

Will my immigration status change, and do I need a special visa?

If you aren’t a citizen or permanent resident in your primary country of employment, it’s essential to consider how being a digital nomad may impact your immigration status. For example, living overseas for part of the year may change your visa status or path to citizenship.

Many countries offer special digital nomad or self-employment visas that you may want to apply for if you plan to stay longer. As you research your options, keep in mind that countries rarely use “digital nomad” in the names of the visas, which may instead be called residence permits or have unique titles.

Should I set up a local bank account?

The need for setting up a local bank account depends on how long you plan to stay local. If you’re emphasizing the nomad part of being a digital nomad, you may want to avoid setting up a new bank account in a specific country. This becomes complicated quickly and may not be worth doing if you don’t plan to stay in the country long.

If you’re going to be a frequent traveler, consider a universal account. This type of account allows you to hold multiple currencies from countries anywhere in the world, all in one place, accessible from all your devices. With a universal account, you can easily handle the currency exchanges you need to travel, where you want to go, and when.

Wherever your digital nomad journey takes you, it’s important to plan ahead and make responsible decisions that will allow your travels to continue uninterrupted for a smooth journey.

Be sure to really engage your employer with your digital nomad journeythe questions above are essential, but if you have more, don’t hesitate to ask them. With the right workplace, insurance, and financial planning, you and your employer can chart a clear and safe course into the beautiful horizon of digital nomading.

Candace Smith, People Operations Lead, Americas, Wise

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