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
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:
- Quit Like a Millionaire, by Kristy Shen and Bryce Leung. Despite the title, this is a surprisingly practical book about early retirement. It probably covers a lot of stuff you're already doing, but it also has advice on how to handle things like medical insurance when living abroad that I knew nothing about.
- The Digital Nomad Survival Guide: How to Successfully Travel the World While Working Remotely, by Peter Knudson and Katherine Conaway.
Most countries make it very easy for US citizens to hang out there and work remotely for an international company for a short time—often 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—what 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!
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!
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. 😅
A colleague who worked abroad while traveling had tips for a shorter trip:
- Check for good and reliable internet access, and plenty of places in which to access it (coffee shops and coworking spaces)
- Stay +/- 2 hours of current time zone to keep a regular schedule for life, and work.
- 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—Bureau of Consular Affairs has more information!