Working Remotely as a Digital Nomad While Traveling

On June 3rd, 2016 my girlfriend and I left San Francisco for New York City, kicking off the start of a 6 1/2 month journey that would take us around the world until we return to California just before the Christmas holiday.

While its all been extremely exciting, traveling for the better half of a year presented an interesting predicament as traveling tends to be expensive, and I'm regretfully not rich (yet). The good news is I already almost always work remotely and most places we've been traveling are significantly cheaper than living in San Francisco, so making the jump to being a digital nomad is relatively seamless. In fact, I did the math on our former San Francisco one bedroom apartment's monthly rent, and it came out to an inane $77.71/day — more than we've generally spent on housing, food, and all living costs combined, especially now that we're in Thailand.

That said, there's still some considerations to be had and a lot of preparation to be made in advance with this kind of trip. This is definitely written from the point of view of a web contractor, but will hopefully be applicable to anyone looking to transition to being a digital nomad for.

Talk to clients as early as possible!

I wanted to believe work would be a 100% seamless transition where clients wouldn't even know I'm on an island in the Gulf of Thailand, but in reality there's going to be a few hiccups along the way. Unless you plan on staying in one place long-term, assume you'll have at least a few days where you don't have a working cell phone and/or internet fast enough to upload your work (or no internet at all). Chances are this will happen more frequently if you're traveling in second and third-world countries, but even in highly developed places like Europe you'll likely find yourself with a few days that are a wash.

While I do my best to avoid these situations whenever possible, you need clients who will be understanding when you do fall off the grid for 24-48 hours (power/internet here sometimes drops randomly for hours at a time!), and if anything be excited for the journey you're about to take. In the event that an existing client (or employer) isn't comfortable with that kind of possibility, you need to work with them to wind things down leading up to your departure, and if possible help them get your replacement up to speed sooner than later.

Be realistic about how much you can work and communicate when you can't.

Working constantly while traveling is not like working at home — it's way more chaotic, exhausting, and ultimately takes time away from enjoying all the exciting things happening around you. 30 hour work weeks may sound like living the dream compared to the 40+ hour work weeks most people experience at home, but when you're hopping around the world on planes and trains there's a good chance those 30 hours will feel a lot more like 60. Plan your work ahead as much as possible, and talk to your client about working extra hours leading up to and following periods where you know you won't be able to put in your normal amount of work. Research where you're going ahead of time, and if you know internet might be spotty be sure to let your client know ahead of time.

Be honest and don't be afraid to turn down clients.

This is arguably good advice for even non-nomads, but it's especially important when your traveling and time is limited. Be upfront and honest with both yourselves and your client(s)/potential client(s) about you can and can't do, and strongly consider not just the number of hours you'll be working, but also the responsibility you'll owe to your client to do a quality job within the timeline you're agreeing to. It's always tough to say no when you've got dollar signs in your eyes, but unless you're incredibly strapped for cash you should aim for a balance between work and enjoying the new culture around you.

Don't compromise just because you're traveling.

I have no idea what was in the water in July, but I personally had an onslaught of potential projects (at least 8!) thrown my way over a period of two weeks, and am forever thankful that I turned down all but one. Of the other ~7 that I turned down, at least 2 asked if I could relocate to their location earlier than the planned end of our trip, and one even asked what my discounted rate was as I was out of the country where cost of living is cheaper. (Spoiler Alert: I only offer “discounted” rates for long-term retainer-based contracts of 2+ months at 40+ hours/month or more as there's an inherent benefit in not needing to constantly follow up on new project leads while managing a dozen different projects.).

There's something to be said about full time salaries being adjusted based on cost of living, but as a contractor you're selling your expertise, skill, and most importantly your time. If a client wants to hire a cheaper overseas contractor they are more than welcome to do so, but you shouldn't make yourself that contractor.

The Internet is your friend (seriously).

There's a huge wealth of resources out there to help you plan around your work needs — use them. My personal favorites have been a few travel staples like and, and a few lesser known ones like and Also, if you're going to Southeast Asia be sure to check out Facebook Groups — while we mostly use Facebook for connecting with friends in the United States, there seems to be a group in each city for literally everything, from meeting other expats to dating to renting an apartment.

Get used to working offline.

I might work as a web designer and developer, but not having internet can't be an excuse for not getting any work done. In the weeks leading up to traveling try intentionally turning off your wifi for a half day at a time and figure out what you can and can't do while offline. Work on gradually making sure anything you normally would need the internet for can be done offline, and if it can't then give yourself a list of alternative tasks you can do in the meantime. Prior to leaving I gradually made sure all my web projects can run locally without an internet connection and training myself to use Dash for OSX to read docs rather than searching online. For one project it admittedly required a good few modifications to the backend server, but more than paid for itself when I was able to do a solid 8 hours of work while on the slow ferry from Athens to Milos in the Greek Isles.

If there's any large uploads/downloads you'll need to make be sure to do them either before you leave or while you're in major cities where connections are fast and latency to US services are low — it's easy to forget when living in the US or Europe, but uploading/downloading to a server on the other side of the world can take 100x as long even when you have a fast local connection.

Work Asynchronously

Taking 1AM calls is part of the deal you make when you choose to work remotely and travel the world, but it definitely shouldn't be the norm. Make sure that whatever client's you're keeping or accepting are used to working in an asynchronous manner via either email, chat applications like Slack, or project management applications like Github, Asana, or Trello. My primary two clients have employees around the world across at least a dozen timezones, and using Slack for almost all our communication has made it barely any different than when I was living in San Francisco. The main thing you (and your client) need to keep in mind is that every sentence counts when you get to be on a 12+ hour time difference. If you forget to say something or you're not clear in what you need, that could mean another 24 hour delay from your original message.

If you haven't already, check out Remote by Jason Fried (founder of 37Signals/Basecamp). It's admittedly at times a bit general, but overall it lays down a lot of common sense principals for both individuals and clients/employers that can help make working remotely successful.

Get a VPN (Virtual Private Network)

While using a VPN for security might be overkill in your situation, you'd be surprised how many websites don't work properly when they detect you're in another country. Paypal alone has already refused to let me access my account in both Greece and Thailand, and without a VPN to route my traffic through the US I wouldn't have a way to get payments from one of my clients to my actual checking account. If you're doing development work there's also a good chance you'll encounter public wifi that (for reasons unbeknownst to me) block port 22, making SSH worthless without a VPN.

If you need to sign up for one I can't recommend Private Internet Access highly enough. Their setup isn't the prettiest or fanciest, but their servers have so far been extremely reliable, as fast as one can expect when routing traffic halfway around the world and back, and they take their user's privacy to an extreme by forcing you to use anonymous usernames, not maintaining logs of any user traffic, and allowing you to pay via (more) anonymous methods like Bitcoin. In at least one case over the past 6 months they've sent a newsletter letting all users know that they were retiring their Russian VPN locations due to concerns over new legislation that would potentially compromise their customer's privacy.

If you're starting a new business, give yourself at least 3 months to be revenue-positive.

Lastly, traveling can be the perfect time to start a digital or online business, but remember that it takes time (and often money) to build something profitable from scratch (it took me almost 6 months of contracting back in 2012 before my income stream was stable). If you can, do as much of the upfront legwork before you leave, and make sure you have enough savings to pay for everything for at least 3 months. In the highly possible event you aren't making enough money by the time your savings starts to run dry, be sure to have a backup plan in place that either lets you jump ship for back home or pickup a local job that covers the bills.

Be Prepared for a “Worst Case [Technology] Scenario”

Within a few weeks of starting our trip, my girlfriend encountered my worst fear: with no prior signs of issues her barely one year old Macbook Pro wouldn't power on. I tried every combination of system reset keys in the book, but as it wouldn't even begin to power on it looked like it was a hardware issue. Unfortunately, we were at the time in Dublin, Ireland where there's oddly no official Apple Store and any secondary repair shops had a 3-5 day turnaround time...not promising when we had a flight to London in two days. We looked at getting it fixed in London, but all their Apple Store appointments were booked a full two weeks out, and the next Apple Store we'd encounter with open appointments wasn't for two weeks in Milano, Italy.

In the end we thankfully we got it fixed (damn faulty Mac logic boards), but as it was just barely outside it's warranty window and under a US warranty (many companies, Apple included, don't always honor warranties from different countries) it ended up being a few hundred dollar repair. There's not a lot you can do to prepare for this one, but just remember that as reliable as your laptop is now, getting it repaired overseas might not be as simple as hopping down to the nearest Apple Store. If having a running laptop is crucial to your work, it's worth having that emergency fund for that unexpected repair or replacement.

Final Thoughts

Working remotely as a digital nomad can be an extremely rewarding experience, just make sure you have everything in order before you hit the road and most of all: communicate, communicate, COMMUNICATE! Almost all problems that come from working remotely can be avoided if both parties are communicating clearly (and honestly) as early as possible.

Have you or are you working as a digital nomad and have something you think would be worth adding? Email me at rob at and let's chat!

![Client meeting in progress](/content/images/2016/08/DSC_0534-edited.jpg)
When things don't go according to plan.An important client meeting in progress from Piraeus Port in Athens via mobile Google Hangouts. Our ferry from Santorini to Athens ran 3 hours late due to rough seas and I had to start the call while deboarding with a thousand other people.