Building a Better Nomad: Things I Learned Working on the Road

Two years ago, I started working with a fabulous and tightly-knit team in Wellington, New Zealand, working on a tool called Loomio. A good majority of that time has been spent being the lone developer working remotely, often in wildly different timezones. Here’s what I’ve learned about being the guy out of the office:


In any line of work, we’re heavily dependent on our tools… the more sophisticated the tool, the more productive we are. Here’s the thing, though: the tools that we’re using to make this nomadic lifestyle work, are really rather primitive compared to the tools we would need to make it work really well (being a lone remote worker is way more along the lines of ‘feasible’ than ‘cakewalk’ at the moment). Chat clients, video messaging platforms, scheduling apps, scrum boards — these are all wonderful pieces of technology which enable the possibility of remote work, but it’s still bit of a chore to interact with another human being through them, and the infrastructure for using these things is, in most places, just barely sufficient. We are, after all, working in things called organizations, companies, cooperatives; we are social creatures working on technology for people, so going off on my own into the wilds of the world with only the ability to see my coworkers on a screen once in a while makes me feel a bit like this guy:

cool hat, buddy

Someday, we’ll have the holo-deck, the teleporter, the space-timezone alignment apparatus, and remote life will be wonderful. In the meantime, though, keeping up is really hard. So, what to do? For me, it’s to use and abuse the tools that we do have, as much as possible. Be really active on Slack. Hop in on that standup every day you can, even if it’s at 11pm. Have one-on-one checkins with your team members, especially if something is tense (as soon as it’s tense!), but also when something is great. Those that are onsite are getting their vibes from the firehose, while I’ve only got a drinking straw, so being proactive and consistent about interactions has really helped me maintain a connection with the people I’m working with. Radio silence is death!

Don’t #YOLO. Aspire to be great at your job.

We (modern day humans from somewhat affluent countries and/or backgrounds, particularly Americans) are often heavily accustomed to the romanticized blitzkreig method of travel: arrive at the airport, hop on the tour bus straight to the giant skyscraper so you can salmon ladder up and hang-glide off to your third cousin’s all-night raging foam beach bash extravaganza that goes till sunrise (“It’s your one night in BARCELONA, bro! You’re watching the &$*#ing sunrise.”), just in time for your 7am train out [which has wifi so you can ship dat module on the way to Berlin (⌐■_■)].

Please don’t do this. It won’t work; you’ll burn out in a few weeks, if not a few days. In order to actually make this a sustainable lifestyle for myself, I had to let go of my hard-coded “foreign countries are the best thing ever, every second is precious, I’m on a GRAND adventure” notions of travel, and become much more pragmatic about managing my time and expectations. No 5-day trips into the wilderness to see the sand dunes and ride the camels, politely declining some awesome cultural experience because of that 10pm call, not knowingly booking a 2-month stay in a place with known spotty wireless, etc.

Yes, the perks of making money while traveling the world are wonderful. One month after work I can go and take a dip in the Aegean sea, the next I can sip some fine wine overlooking the vineyards of Italy, the next go out to some out-of-control rave in Southeast Asia (this is, in fact, the plan), but I’ve needed to take the ‘work’ part of my life quite seriously in order to sustain an acceptable level of productivity. When I’m working abroad, even more so than being in an office, I alone am responsible for the quality and quantity of my work. Allowing it to get to a point where other people are questioning me (“Hey, I haven’t heard from James in a day or two… wonder when he’s gonna get that thing shipped..”), means I’ve already failed. There is a tendency out there for folks (likely at Loomio, definitely almost everywhere else), to think that we (developers and other professionals who are constantly on the road, often in exotic locales) are on one long vacation, sipping from coconuts on the beach as we half-heartedly tap away at our keyboards, toes in the sand, so that the currency shows up for the next adventure, but It’s important to me that this isn’t my experience.

Why? Because work doesn’t get easier when you’re on the road, and in fact the ‘job’ part of my life got quite a bit tougher when I started traveling. I can’t stress this enough: working remotely makes the ‘work’ part of my life, way worse. Even for an employee who is massively competent, diligent, and communicative (I’d be lucky to scrape 1 or 2 of those), the communication barrier, time constraints, inconsistent schedules, distractions, and having to manage the uncertainty of being a foreigner every week of his or her life, will invariably mean that he or she will be less productive on the road, no questions asked. And, I have a really strong desire, not to just have a job, but to be really good at my job. So, I work more. I work weird hours. I’m diligent about being in touch, making my voice heard, and keeping myself relevant and informed (no one can do this for me — it requires an active and consistent effort), while also being my own QA department and making an effort to deliver code that doesn’t require days and days of back-and-forth. It really is a wonderful exercise in autonomy, for those who are into that sort of thing.

PS — I’m not sure why the digital nomad community has picked ‘working on the beach’ as our chosen trope — working on the beach sucks: sand, noise, children, extreme sunlight? Not I said the James. Go to the beach after work. I guess I’d liken it to making out upside down, or maybe running through a wheat field: Romantic, but unpleasant.

Budget time for travel planning

I’ve never been a great planner. But one thing I didn’t (explicitly) realize before going on the move was the amount of time commitment travel would require in my life, especially when I’m moving around frequently. It’s nothing short of a small part-time job to be your own travel agent, and I have to treat it as such or it doesn’t get done.. which is always when the disaster happens (I pretty much always have a foot in the door to homelessness, any given week). Every time I change locations, I feel the need to answer some to most of the following things:

How am I getting there?
What’s the visa situation? How long can I stay? Do I need an onward flight?
Where am I sleeping? Where could I sleep if that doesn’t work out
What’s the currency like there, and based on that, what’s my budget for this leg of the journey? Do I need an ATM before, or right after I arrive?
Where am I going to work? How’s the internet there? What happens if the internet happens to suck? (this can get particularly tricky when I’m scheduling calls late at night because of time zone differences, and coworking spaces / cafes / Starbucks aren’t open.)
Can I cook there? Where’s the supermarket?
Who do I know there, and where / how can I meet people?
Where do I wash my clothes?
What do I want to do in this city? Cuisine? Touristing? Work? Networking?
If there’s a time zone difference, how am I going to deal with it? (Getting your time clock messed up is a real danger if you’re moving around quite a bit.)
Can / should I rent a bike / scooter / car while I’m there?
What’s the public transit like? Should I look into a weekly / monthly pass if I’m there for that long?
Do I know the language at all? I should probably at least know ‘thank you’ and ‘sorry’…
How’s the crime rate? What about the political climate? What if all hell breaks loose? Where is my embassy and can I get to it if I need to?

These are all coming from someone who’s prettay low on the dependency / risk aversion scale as well… depending on your temperament you may feel the need to worry about travel insurance, health insurance, prescriptions to take, setting up a VPN, verifying your phone plan, dealing with your bank, ensuring that you have backups (or backup plans) for losing essential things like laptops / chargers / phone batteries, the list goes on.

Even trudging through this checklist once a month (much less once a week) is a very daunting, time-consuming task; for each time I change locations, I budget between one and three full days of administrative, planning-style work to get all of these things under control; suffice it to say that there’s a decent amount of unpredictability and not a small amount of anxiety which comes with this territory, and allowing time in my schedule to cope with both correctly is essential.

Know yourself

When I first started writing this blog post, I had ‘Establish a routine’ as a bullet point to talk about. Many people who are talking about working remotely heavily stress the importance of establishing some kind of consistency in your life when things are changing so rapidly… but I’m pretty much the worst person out there around having a routine, and still to this day I don’t have one, at all.

For me, I’ve found much more value in being humble, flexible, and painfully self-aware (no delusions of grandeur or anything else!), which has consistently helped me find my productivity even on days where it didn’t seem to exist. Maybe it’s finding a new physical space, a new head place, a different task to work on, or different company to keep, but knowing my preferences and limitations as a worker and being honest about brain state has been really useful in keeping myself productive and not burnt out.