There are some free spirited people out there that can drop everything and move to a new country on a whim. With nothing but a backpack and a plane ticket they face the challenges as they come with no thought to plans or schedules. If something goes wrong… oh well! It’s all a part of the journey. Life is an adventure, planning is boring, and so on.
Jess and I are not those kind of people. Our lives run on well ordered to-do lists and detailed calendars. We started planning for our life abroad more than a year in advance. When we decided to go remote and leave the country we had a thousand questions and there were a lot of things we didn’t even know that we didn’t know. How will we find places to live? What if we get sick while we’re abroad? Do we still have to file US taxes? Is IHOP really international?
With a lot of internet research, phone calls, and conversations with other expats we were able to answer most of our questions and come up with a plan. There are still surprises, but now we’re in a pretty good place now to deal with them. If you’re looking to take your work remote and do some traveling or if you’re just curious about what we’ve been up to then keep reading. This is our supercool no-nonsense guide to living abroad and working remotely.
This is a big one. Finding a job that allows remote work is no small task, although some professions make it easier than others. Jess and I are both software developers, which is a pretty good field to be in for this kind of thing. If you’re a dentist then finding remote opportunities will be a bit more challenging. But before you go updating your resume you should try floating the idea of remote work to your current employer, if you have one. If you’re comfortable in your job and your managers trust you then they might be more than happy to let you work outside the office. Desk space isn’t cheap. And the worst thing they can do is say no, so there’s no harm in asking!
If it turns out that you will need a new job then there are some resources available to help in your search. These sites are tailored for remote workers or at least make it easy to filter by remote positions. But, as is the case in all job searches, nothing beats a solid professional network. If you know people at remote-friendly companies, reach out to them first! If you don’t know anybody then head to some networking events and ask around.
- We Work Remotely - This is a job board featuring only remote positions and it covers a broad range of fields and industries.
- Remote.com - More than a job board, this site lets remote companies and invidiuals fill out profiles and then tries to match the best fits.
- Stack Overflow Jobs - This one is geared primarily to tech workers. Stack Overflow offers a great job search and makes it easy to filter by remote positions.
- Indeed - Indeed’s job board isn’t remote-specific, but it’s easy to filter by keywords. But be careful! “Remote” means different things to different companies. Some (ridiculous) companies say they are remote when really they mean you can work from home one day a week.
If you want to work remote you’re going to need to know the tools of the trade. You will be asked about these during interviews. First and foremost is Slack. This messaging platform has become the de facto standard in workplace communication (at tech companies anyway). Slack makes it easy for whole teams to stay in touch and it makes it even easier for your coworkers to bother you during dinner. For better or worse Slack is everywhere. If you’re not already using it professionally or as a part of a community chat then you should start now. It’s easy to get started and available for all major platforms.
I would also recommend familiarizing yourself with some type of video conferencing software. Adding a video chat to your meetings is a great way to get face time with your coworkers who you may otherwise never see. Any remotely friendly company that you work for will have a preferred service, but they’re all pretty similar, so if you’re comfortable with one you should have no problem navigating the others. Check out BlueJeans, Zoom, or Google Hangouts to get started.
Being comfortable with remote work does not guarantee that you’ll find a job right away. Finding a good fit in a remote friendly company is a difficult process. It took me many months and many rejections before I was able to get my foot in the door (I applied to over 100 jobs). It was my experience that a lot of prospective employers open with the question “Have you ever had a full-time remote position in the past?” And so I was stuck in a catch-22 where I needed to already have a remote job in order to get a remote job. It was frustrating to say the least. Perseverance and networking were crucial for me.
I also found that many positions that were listed as “remote” were really only remote a couple days a week, or required employees to live near the company headquarters. When I first started looking I wasted time interviewing at companies that did not share my definition of “remote”, which was pretty frustrating. Make sure you clarify what you’re looking for up front to avoid the same mistake. And feel free to berate the recruiters for misrepresenting their jobs postings.
One more thing to be aware of is that many US employers are not comfortable having full time employees living abroad for tax and legal reasons (This is the only explanation I could ever get, your guess is as good as mine as to what those tax and legal reasons are.) You may have to be willing to take a 1099 contractor position instead of a traditional W2 position. There’s a good overview of the differences between these employment types at The Motley Fool. For me this was not ideal, but life is all about compromise.
As an alternative to traditional full time employment you could also try freelancing. I haven’t done this myself, but it is a popular choice among those who like to travel and work on their own schedule. The income is not as stable and finding clients can take a lot of time, but in terms of flexibility this option can’t be beat. No bosses and you get to set your own hours. It’s perfect for the world traveller that doesn’t know what time zone they’ll be in next month. Check out Fiverr, Upwork, or Freelancer for potential leads.
Finding a remote job is a big step, but it’s not the only one! There are still a lot of things to think about. Housing, packing, visas, vaccinations… the list goes on. Stay tuned to read about some of the other things to consider before buying that plane ticket. If you decide to throw caution to the wind and leave without preparing then don’t blame us if you end up stranded and helpless, just like Tom Hanks in that one movie.