Lessons I learned on the road as a Digital Nomad

Change, infrastructure, travel, gear, accommodation and more.


This article lists some of my more practical nomad hacks from this year with accompanying iPhone/VSCO snaps. There’s been quite a lot of Digital Nomad discussion as of late. It’s a title which will become commonplace a few years from now. Till then, we as a community still have many experiences to share, here are mine.

Note: This article doesn’t discuss travel as a whole. Travel insurance, handling money, air mileage programs, dealing with corruption, jet lag, learning languages, freak street food, etc. These are all covered in full elsewhere already.

First trip of the year — Paris, France (Credit: Manual Schmalstieg)

Change one thing at a time. Being a nomad brings chaos to your day to day. If this is the road you want to go down, other variables need to be on lock. Don’t try to transition between responsibilities whilst traveling between countries.

Don’t say “I’ll be my own boss” without knowing exactly what you’re a boss of. Traveling constantly exposes you to (good) distractions whilst also being in pursuit of reliable infrastructure. Your work is the one thing that shouldn’t shift dramatically as you change locations. You need to have a strong vision of where you’re going, even if ultimately you have no idea where it’ll take you.

In practical terms, you should have a granular and established way of generating income. As I’m constantly on the road, notepads have become impractical, so I use two Trello boards to collect all professional and personal tasks. Whilst it doesn’t have offline capability yet, they are working on it. Your routine should be strong enough to be able sit anywhere and get into it within minutes, you need to have a system for work as opposed to simply being reactive to email.

Byron Bay, Australia (Instagram)

Travel light. After 45 flights in the last 12 months, there’s no place for checked luggage. This goes without saying, but all you need is a carry-on.

The traditional Digital Nomad (as we’re led to believe) pursues a sunny and warm path. If the same applies to you, there’s no need to bring anything more than a few tees, shorts, flips flops and your work gear. Other things you need can be sourced/shared on site; shower stuff, sun cream, etc.

Take pride in purchasing for quality and flexibility, price isn’t always reflective. Luminox watches are great in and around the ocean, Gillette “Sensitive” blades are fine if you don’t have shaving cream and the Skross World Travel Adapter hasn’t failed me yet (the NomadClip is also cool).

Your carry-on will often be overweight (limits have been reduced to a typical 7–8kg), have a secondary bag ready to go. I already pack all of my work gear in a cinch bag inside of my carry-on as I don’t want to be fumbling around the overhead compartment inflight. Carry-on luggage gets beat up in no time, consider Tumi or Samsonite for something more rugged.

London, United Kingdom (Instagram)

Complete Infrastructure. Infrastructure isn’t synonymous to internet. If your idea of being a digital nomad is taking your laptop with you on a vacation, then you can’t really appreciate the need for a complete infrastructure. Everyone has a routine, in most cases you don’t need to sacrifice essentials in the slightest. If you don’t plan however, you’ll invariably break routine which in turn impacts work.

If you’re backpacking, staying at youth hostels, there’ll likely be more downtime trying to sort stuff out. If you freelance, increase your rates to the point that you can continually afford a setup that respects your time. For me that’s reliable WiFi, a kitchen, laundry facilities as well as close proximity to a gym and a decent grocery store. I’m not compromising on what I had before, I simply have to plan for it more than before.

Night Market, Phuket Town, Thailand (Instagram)

Exercise. Especially with the shorter trips, it’s easy to completely bail on physical activity whilst doubling the nights out. I’ve fallen prey to it, but have gotten better about it. The key is not to rely solely on the gym experience, but on independent tools. Besides running and swimming, there are bodyweight exercises and TRX as nice additions to cardio (both of which have plenty of apps for all phones). The only downside of TRX is that it weighs in slightly under a kilogram.

As with any exercise, it’s always more motivating/productive to do it with others. Recruit or team up with people from your co-working space, surf classes or otherwise.

If you’re a gym rat (I still enjoy using them), you’ll get a daily rate at any establishment. Again, negotiate for the term you’re staying. As you’ll have odd dates, it’s easy to negotiate on (i.e. getting 6 weeks for the price of a month). Don’t let travel break this routine.

Empty Airbus, over the Gulf of Thailand (Instagram)

Accommodation. I mostly stick to Airbnb (entire home/apartments) because I want to minimise uncertainty. A clear and concise listing with multiple reviews mitigates that. You’ll have plenty of other things challenging you in your new environment, be smart about which ones you can already take care of before landing.

There are two nomad advantages that provide room to negotiate on Airbnb.

First, the average Airbnb guest stays for anywhere from 3 to 7 days. By being someone that is seeking 30 or more days, you become of great value to a host. You’re cutting down on their administrative time (correspondence, welcome tour, etc.) as well as removing frictional downtime (gaps between guest stays).

Second, the average Airbnb guest books 30 days in advance. By booking a few days before, you’re creating a last minute opportunity for a host to make (any) revenue. Whilst Airbnb is trying to cater towards this impulsive behaviour, there’ll continue to be ample supply of hosts willing to negotiate.

Good reviews go a long way in creating trust and opening the door for negotiation.

There’s a third opportunity unrelated to being a nomad; take a risk and go with your gut feeling on zero review places. Promise to write a comprehensive review in exchange for a discount.

The above is certainly not an exact science. As a baseline, I’ll get 10% off any normal stay (staying one week, booked a month in advance) after a simple message asking if they’re running any deals. Beyond that you’re looking at anything from 20% to 50% off.

Brooklyn Bridge, New York City, USA (Instagram)

Work environment. R.I.P. battle-station with multiple screens, ergonomic chair, keyboard, surround sound and all the other toys. I thought I’d miss it, but it turns out a mouse and great headphones go a long way. I usually bring three headphones with me. The traditional Apple ones, some in-ear RHA’s and my Sony MDR-1NC. Blocking out noise is vital for my work and finding flow. I have a work Spotify playlist here and @philip_arthur also has a good one here, go premium to have that offline availability.

Most places you’ll stay at will have also have an LCD TV so why not use it as a second monitor? Invest in a cable (like the one above) that has a male HDMI end and you have a big screen everywhere.

As for where to work. Co-working spaces are spawning everywhere and they’re really growing on me. There’s ShareDesk, desksurfing and other aggregators. As I write this, I’m sitting in The Surf Office in Gran Canaria, a definite to-do for anyone looking to surf and work in Europe. Whilst cafe’s are cool too, it’s simply not the same. I’d rate non-professional spaces roughly one third less productive. Again, eliminate uncertainty in advance where possible.

I’ve also written on increasing productivity and work quality.

Playing it by ear and ending up in Starbucks is a cop out.

Airbnb, Manly Beach, Australia (Instagram)

Press Pause. Traveling as a nomad isn’t a vacation, you need plenty of time to work comfortably without feeling rushed. What’s the point otherwise?

I fell into the nomadic lifestyle by accident after a number of back to back trips for work. These trips were short in nature, never longer than one or two weeks, sometimes just a day. This doesn’t create enough time to settle down, relax and reflect. At that stage, we simply get stuck in execution, failing by defining ourselves as being busy. Need proof? Simply track the sort of work you do while you’re traveling using Rescue Time.

It’s crucial you take at least four to six weeks in any given location to hang around and take it all in. Having a co-working space that goes a step further (providing accommodation, doing activities) like here at the Surf Office help ease those travel pains. Travelling in groups provide a similar experience as long as you’re aligned on goals/intent.

El Cotillo Beach, Fuerteventura, Canary Islands (Instagram)

Prepare for offline. It’s inevitable, you will be offline, a lot. You can mitigate that stuff with some planning; cheap 3G SIM cards or getting a dongle (say you stay in Spain for a few months every year, invest in an annual subscription).

That said, it’ll still happen that you’ll be completely offline (which doesn’t have to be a bad thing, the contrary rather). In those cases, before switching locations, I do a few things:

  • Pull down all current GitHub repo’s for active branches.
  • Sync ReadKit / Pocket
  • Sync Kindle reading positions across devices (I like to bounce between 2–3 books at a time on both MacBook Air & iPhone, don’t have room for a physical Kindle).

If you’re going to Eastern Europe, ignore this comment (free and open WiFi everywhere). If you’re going to Australia, bring your wallet and patience.

As airports and airplanes build more power sockets and laptops stay on longer, the question of power is becoming less of an issue. A 13" MacBook Air will run you up to 12 hours (as long as you halt vagrant and other battery draining services).

An external battery pack for your phone is also always helpful, be considerate of weight though (they easily get to half a kilogram).

Trysil, Norway (Instagram)

Connect. Regardless of your reasons for hitting the road, find time to touch base with other nomads and travellers. I’m always amazed at their stories, travel hacks and perspective on it all. The title Digital Nomad (much like Growth Hacker) is somewhat glorified, however it is easy to search for and only has a single popular hashtag (#digitalnomad). There’s even a conference (DNX in Berlin) and some communities trying to aggregate individuals (Nomad Project).

As for my travels after the Canaries? ✈ Zurich, CH ✈ Sofia, BG ✈ London, UK ✈ San Francisco, US ✈ Las Vegas, US ✈ TBD (Bali/Thailand). Hit me up!

Ao Phang, Phuket, Thailand (Instagram)

Follow the journey on twitter and instagram