Traveling abroad while working remotely?

Hi YNAB (and forum community)! Since the entire company works remotely, I thought you might have some wisdom or resources to share with those of us who may want to do the same while traveling abroad. I've never been a "where do you see yourself in five years?" type of human, but I'm realizing that I would like to arrange my personal and professional life over the next year or two to accommodate my life-long dream of extensive travel. As a US citizen, could you tell me where to start my research and prep? I'm especially curious about what would be required if I have clearance from my US-based job to work remotely full-time



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  • Hi Sky Blue Rhythm ! That is a really fantastic question. A few of my colleagues may have tips to share. I've asked for their thoughts, and will let you know when I hear more! 

    I'll be eagerly awaiting the answers as well. 馃槀

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  • Hey, Sky Blue Rhythm !

    I've never truly done the digital nomad thing, but I've definitely clocked in for work from a couple of different countries.

    It may seem weird to recommend dead-trees books first, but I have two that come to mind:

    Most countries make it very easy for US citizens to hang out there and work remotely for an international company for a short time鈥攐ften 90 days, sometimes up to a year, on a tourist visa or visa-waiver program. If you want to stay somewhere longer than that, it may get tricky, but it depends a lot on the country.

    I think if you get the money and health insurance parts to fall into place, the biggest challenge will be establishing a routine and minimizing loneliness. I've been working remotely for quite a while now, and when I'm traveling solo, I really need to make a plan to meet up with humans every day. That can be with local friends or a Meetup/Facebook group.

    One of my most successful recent work/play trips was to Tokyo, where I stayed for a week with a family that I found on Airbnb. It was a tiny spare room in their house, and being able to come home and have a beer with my "host parents" at the end of the day made a HUGE difference. Even if you can easily afford not to travel backpacker-style, consider doing it sometimes anyway鈥攚hat it lacks in privacy and amenities is (sometimes!) made up for in human connection.

    I'd love to hear more about what kind of lifestyle you have in mind, and I'll be happy to jump in with more specific tips if I have any!

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    • Matthew thanks for this answer, and apologies for the delay! I read the Digital Nomad Survival Guide (great resource), and I love your anecdote about staying with a Japanese family. I had a lot of great experiences with about a decade ago, and I think I would definitely dust off my account to meet up with locals while working abroad.


      I'll admit that COVID and the like have sidelined my research, but re-reading your OG comment has me wondering if the "International company" means that the company itself has to have a footprint outside the US in order to take advantage of the 90 day guideline? I'm going to have to pull out my copy of the Digital Nomad survival guide and get back to researching.


      The cool personal news is that my company has approved remote work, and i will be taking advantage of that stateside for the time being. Phase two would be to cut the cord on the requirement for a domestic location -- your input has been really helpful at taking the next right step to research and prepare. Thanks so much!

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    • Sky Blue Rhythm No worries鈥攇reat to hear from you!

      I'm definitely not an immigration law expert, so take this with a big grain, but I meant "international" in the sense that the company does not have a footprint in the country where you're working. In the case of Japan, for example, the immigration office probably wouldn't care if I showed up and spent 90 days working remotely for YNAB on a tourist visa. (That's setting aside current travel and quarantine restrictions, of course!)

      What they don't want to see on a tourist visa is anything that ties you to the local labor market, and that includes: working for a local branch of a foreign company, working for a Japanese company, or opening a local bank account.

      Again, the rules on this sort thing change all the time, and it's possible what I'm describing is more of a legal gray area than actual law, so please do your own research!

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    • Matthew  That makes a lot of common sense, but I absolutely will do my own due diligence before making any major moves. Thanks again for all of the input, and I will follow up if I learn anything that may benefit other thread visitors. Hope you and your loved ones are all safe and well. 

      Like 1
  • Hello!

    I am curious about this too. I have looked at many of your job postings (hoping to find one that fits my skills one day!) and it says that if you live abroad they will make you a contractor. Is there anyone on the team that is a US citizen that is living and working abroad fulltime? If you are a contractor, are you considered self-employed and have to pay self employment taxes to the US?

    If you have any insight on this, I would really appreciate it!

    My wife is starting a postgraduate program in the UK and I got the okay from my work to work remotely and trying to figure out the tax implications!

    • Lavender Major  I'm glad you boosted this because I have been meaning to reply with a followup! I'm looking forward to hearing more on the topic.

    • Lavender Major  Yes, employees who live abroad are brought on as contractors. To get email alerts on new job openings, you can subscribe at the bottom of this page. If you haven't already! We're careful about the privacy of our team members, but I'm going to check with our Hiring Manager to see if she has anything to add.

      Congrats on getting the okay to work abroad! That is really exciting. We're not able to provide financial advice, but an expat tax professional can help make sure your bases are covered!

      Like 1
  • So sorry for the delay, Sky Blue Rhythm ! I shared this with the team back in February and it got lost in the COVID chatter mix. 馃槄 

    A colleague who worked abroad while traveling had tips for a shorter trip:

    1. Check for good and reliable internet access, and plenty of places in which to access it (coffee shops and coworking spaces)
    2. Stay +/- 2 hours of current time zone to keep a regular schedule for life, and work.
    3. They wanted to go somewhere less expensive than the US (and warmer).

    In her experience, each country had different requirements to meet and they chose based on the above, and checked their embassy websites. The US Department of State鈥擝ureau of Consular Affairs has more information!

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    • Nicole Thanks so much for following up, and please don't apologize. The last three months feel like three years. The time zone difference makes sense; although I was hoping it might be possible logistically to slowly transition through time zones as I work abroad to soften the blow to my circadian rhythm -- but that of course would only apply to a longer trek around the globe. 

      At the risk of repeating what I said in my reply to Matthew up-chain, I will follow up here if I learn anything that other thread visitors may be find relevant/interesting as I keep doing research. I hope you and your loved ones are all safe and well.

      Like 2
  • By "clearance", do you mean "approval" or are you talking about a security clearance?

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