Disclaimer: You asked for advice. We’re providing it. But as with anything else, make sure you check with the actual professionals to make the right decision, especially when it comes to immigration.

Q: During this Covid-19 crisis my company has decided that we will be working remote for the foreseeable future. I’ve decided that I want to go abroad and work remotely from an international location. I am not sure if my employer will allow it, but I’m still considering it. What should I do?

A: Well, if there’s one thing that the current pandemic (or a political crisis) has caused people to do – it’s to consider their options. If you’ve wanted to try out the digital nomad life or just go abroad, this may seem like a good time to do it, assuming you can get into your desired country.

Before you hop on a plane though, you need to make sure your idea makes sense for your situation. You really need to check if you can reasonably do your job abroad. I assume since you’ve probably been working remote for a few months now, that answer is most likely ‘yes’. But you need to be clear on when your job might resume in-person duties. If it’s looking like a few weeks, then this may not be the best plan. If it’s well into 2021 (or even beyond), this might be feasible.

Secondly, you may actually want to talk to your employer. Given how unpredictable 2020 has been, you never know what their reaction might be. They might say yes. They might say no. But at least you won’t have any confusion as to their thoughts on your plan. However, the real reason you may need to check on your employer’s policy – is for the financial implications.

Depending on how long you are gone, you are no longer in your state of residence – and the company needs to know that, because, well the IRS. There’s a reason why you complete financial paperwork before you start a job. Your physical residency matters and this could be an issue for tax reasons for everyone.

Right behind that is any supportive benefit you receive, such as medical care coverage. You need to know if your health insurance is going to be accessible once you’re out of the country. And even if you are just going for a relatively short period, such as six months or less, you still need to plan for emergencies abroad.

If you decide to do it even if your employer says no, you are going to have to work really hard to cover your tracks. Really cover your tracks. Everything from synching your calendars to the right time zone to ensuring your video call background people can see doesn’t give anything away. You’ll also have to give your social media privacy settings a workout. Plus, you need to be sure that your prospective location has the appropriate internet connection to make sure you can still do your work.

You do need to understand if your employer finds out, this might be grounds for dismissal from your job. If they can point to an explicit policy or prove that you knew the rules, the company may be within their rights. If that’s the case, you’ve just lost your income unless you have money coming in from somewhere else. However, if that income is what you are primarily using to gain legal status in your country of choice, you could also jeopardize your legal standing to remain in that country. In addition, unless you’ve saved up, you might just run out of money and being abroad with financial instability is never a good look.

If you’re going to go through all of this anyway, maybe it’s time to seriously plan for moving abroad, for real.

Q: I purchased a flight from the US to Sint Maarten, Caribbean with a six month return. But I want to stay a year. Will I be able to extend? How do I go about finding out if I can?

A: First of all, just know, I’m jealous and trying to figure out how to fit into your suitcase! But more importantly, if I were in your shoes, I would start with checking in with the nearest Sint Maarten Embassy or Consulate to get the most accurate information available. Since you are a US citizen/resident, you can also visit the US Department of State’s Travel page for Sint Maarten which provides clarity for those from the States. Happy Travels!

Need advice? Ask away. Questions may be edited for length and clarity.

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