Digital Nomad Advice For Working On The Road: What I’ve Learned On My 100-Day Journey

Working as a digital nomad is an interesting lifestyle. A couple of years ago, I gave up the whole “having a residence” thing and became full-time homeless. I started out by spending a decent amount of time in each location I visited, and I wrote about this part of the journey here.


Now I’m in a new part of the journey. As I write this, I am in the middle of a 100-day trip around the world. I don’t know how many countries we’re visiting (20-odd? Maybe 30?) and we’re staying in each for periods ranging from one day to 16 days.

In the midst of this, I’m bringing an unschooled tween, and I’m working on the road.

I’ve been gone for a month now, and I’ve picked up a few tips along the way, many of which are things I couldn’t have imagined before taking a trip of this scope.

Shall we?

Digital Nomad Power

Yes, wifi matters. But power matters more.

There was a time when reliable wifi was the absolute most important factor in digital nomad work and travel. No wifi, no work. No work, no money. No money, no travel. Bad, bad, bad.

That has mostly changed. Most of the developed world has consistent wifi if you know where to look and how to ask for it in the local language. Cruise ports have free wifi on the dock. Coffee shops, McDonalds, even gas stations have wifi. Every mall I visited in Japan had free wifi that was so fast, it put my high-speed at home to shame.

I’m going to go out on a limb here and say that unless you’re running live video, wifi will almost never be a problem.

Power, on the other hand, might be.

First, the obvious. It’s possible that your stuff doesn’t go into their outlets. Easily solvable with converter thingies, sure. But when it comes to extended travel, you run into another problem.

See, any idiot can find a place to charge a phone. An iPad. A laptop. But sometimes you need to charge a phone and an iPad and a laptop. If you’re bringing a tech addicted 12-year-old, you need to charge two phones, and two iPads, and two laptops. Each of those items is connected to wifi and/or Bluetooth, which eat power like certain children of mine eat conveyor belt sushi. They don’t so much use power as hoover it.

Most of us can work without wifi. None of us can work without power.

To navigate this issue, be prepared in two ways.

First, bring converter thingies. Bring enough to simultaneously charge half of your devices at one time. (More than that and you’re taking too much space in your luggage, and no hotel room has that many outlets anyway.)

Second, make a charging plan. I can charge my phone (a Huawei) in about an hour, but my iPad takes so long it’s not worth counting. If I have a limited charge ability, I have a charging priority list so that everything that matters gets done in the most efficient manner possible. (1. My phone. 2. Jack’s iPad. 3. Jack’s computer. 4. My computer. 5. My iPad. 6. Jack’s phone.)

And seriously? Find power and hook up to it the instant you get to a new location. First charge, then pee. You can pee anywhere.

Digital Nomad Sick

You will get sick. Bring drugs.

Once upon a time, I got sick in America. I went to the store to buy a popular brand of cold medication, one I believe is produced and distributed by Proctor and Gamble. So… not an obscure brand.

When I arrived at the drugstore, I could not find this item. In fact, I could not find anything remotely like it. After much searching, I asked the pharmacist where I could find it. She gave me a look like I was asking for the BDSM section and told me that it was a restricted substance.

Um, what?

Apparently, the medication that I take over 200 days a year is used to make meth. I would be permitted to buy six tablets… as long as I provided my traveling address, my home address, my full contact information and a photograph of my driver’s license. (I was going to ask if she wanted a urine sample, but I thought better of it. She looked pretty cranky.)

(For reference, in allergy season, six tablets will get me to just before dinner.)

Contrast this with France.

I had a cold in France and went to the pharmacy there. Where was the cold medication, I asked. This time, the employee didn’t look at me like I wanted pornography. She looked at me like I was asking a chef where I should go to cook the food myself.

France, it seems, operates a little differently. You don’t go to the cold aisle and pick a medication. Mon dieu! Like French farmer’s markets where they pick your fruit for you based on when you intend to eat it, in French pharmacies, you go to a highly educated pharmacist and describe your symptoms.

In detail.

A lot of detail.

What kind of cough? Is it worse in the morning? Sneezing? Does it hurt when you sneeze? Is it green sneezing? Headache? Where in your head? Bridge of your nose, or one inch higher?

After I ran this gauntlet, I was handed a small box with little ketchup packets of medication inside. They tasted like the best Frappucinos you’ve ever drank, and I got enough for one illness. (I went back and asked if I could buy more to take home. Mais non! She was horrified. My next cold would be different, and therefore require different medication!)

There is no way on earth to anticipate what kind of sick you will get when you travel, nor what the region’s attitude is towards that kind of sick. Bring drugs for allergies, colds, coughs, headaches, and anything gastrointestinal.

(This is particularly true on cruise ships, which I find the cheapest way to travel long distances. If you even intimate that you’re sick, they will quarantine your ass. Bring your own meds.)

I travel with one carry-on suitcase, and a dizzying percentage of that space is devoted to medication.

Digital Nomad Jetlag

Jetlag is like Peeves in Harry Potter.

Have you read Harry Potter? Do you remember Peeves?

Peeves is an annoying poltergeist who featured heavily in the Harry Potter books, but did not appear in the movies. If you haven’t read the books, “Peeves was essentially an embodiment of disorder and took great pleasure in constantly causing it. His looks reflected his nature, which those who knew him would agree was a seamless blend of humour and malice.”

During extended travel, that is what jetlag is like.

When you’ve only traveled from one sensible location to another sensible location, via airplane and for a sensible period of time, jetlag usually a pretty straightforward business. A few days of falling asleep in soup bowls, interspersed with staring at dark ceilings, and you’re back to your old self again. However! If you are going to 30 locations and traveling via a combination of high-speed train, plane, and boat, Jetlag Peeves shows up and creates total pandemonium.

On the first leg of my journey, I changed my clock 11 times in 20 days, for a total change of 13 hours.

I cannot explain to you in words how chaotic that was on my system. I thought to myself, “Ha! It’ll be great! I’m traveling by ship! I’ll change a little at a time! No jetlag!”

Horsefeathers. I was a ruined shell. Jack’s sleep schedule did not so much change as become a daily random number generator. “It’s seven, let’s sleep! Which seven? Who cares!?”

I had plans. I had things I was going to do. They all went to absolute, unmitigated shit.

My advice for this issue has two options. You may choose the one you prefer.

One, don’t work on transoceanic crossings. Drink some Champagne and go to bed like a reasonable person.

Two, plan for an amount of time to work per day, but do not even kinda make a plan for when that time will occur. Whatever you think, you’re wrong. “Work at some time while you’re awake.” That is your schedule until further notice.

Digital Nomad Suitcases

For the love of Christ, buy a light suitcase.

I have a fantasy I like to think of sometimes. I like to think that I’m this insanely organized, experienced digital nomad, accustomed to traveling on the road. Like George Clooney in Up in the Air. And on a level, this fantasy is sort of accurate. My computer does fit in an envelope, and I can travel with just a carry-on, and I have an amazing three-camera set-up (including optical zoom!) using only my phone. Looking in from the outside, I’m so awesome it hurts.

The inner workings, though, are quite different. Every leg of a journey is a 3D, real-time, competitive Tetris game where your opponent is God and the referee is an angry, overworked airline employee, weighing your results down to the gram.

See, when you’re going on your honeymoon and all you’re bringing is three bikinis, 50 Shades of Grey, and some suntan lotion, a carry-on bag is quite light. But when you’re working, it’s different.

The things you need to work on the road are often really heavy. If they’re not heavy, they’re bulky. If they’re not bulky, they’re weirdly shaped. And if they’re not weirdly shaped, they’re delicate. Chargers and converters and headphones and lithium batteries and microphones… they add up. It gets intense. And on a level, there’s nothing you can do to avoid this.


You can mitigate it by buying the lightest suitcase you can possibly find.

You need a light suitcase. You need the lightest suitcase. You need a suitcase that weighs less than sunlight.

Here’s a guideline: If you can’t easily lift your bag with only your pinky finger, it’s too heavy and you’ll hate yourself later. Buy something light. Pay whatever it costs.

So that’s the work stuff.

That will get you started for working on the road. Since that’s what this article was about, I will mostly leave it there. Nobody asked for my tips on the other lessons I’ve learned while traveling, which primarily revolve around staying reasonably attractive while living in what amounts to a snug banker’s box. But! I cannot let you go without one more thing I’ve picked up.

Digital Nomad Minimalism

Bonus Non-Work Tip. Be prepared to throw out everything you own.

The Buddhists have a metaphor, for when you buy a beautiful new cup. They say, to avoid attachment, that you should envision the cup as already broken. Then you won’t be a wreck when the cup inevitably leaves you.

I would recommend you do the same thing with your travel gear.

The first stop on my itinerary was Alaska. As I have been researching this trip for over 6 years, I have done my due diligence and learned everything I had to learn prior to departure. The most important thing I learned about Alaska in September was this:

You will freeze your ass off and it will rain every second. Water resistant is a joke. You want water proof. (But you’ll still freeze your ass off.)

So I packed accordingly. I dutifully trotted off to MEC (Canada’s REI) and kitted us both out in Alaska approved gear. That meant that I didn’t have a lot of suitcase room left for “looking demure in Tokyo” or “staying sexy in Rome”, but I was a responsible traveler and erred on the side of caution.

Then I went to Alaska.


It was so hot I got a SUNBURN.

Alaska was hot, Russia was hot, Tokyo was hot, and now I’m in the Mediterranean, which is, predictably, also hot.

I brought enough hand sanitizer to sink a ship, sensible Bluntstone boots, and a metric ton of cold weather gear. I brought a travel diffuser, adorable smelling body cream (in lovingly prepared 100 ml containers), 2-in-1 shampoo and conditioner, and versatile leggings.

I’ve ditched the lot.

All of my clothing was completely inappropriate for Japan, where women are impeccably dressed, AND Italy, where women look smoking hot. (God knows what awaits me in South America.) Every decent hotel in the world has lotion, and shampoo, and plenty more if you go down and ask nicely at the desk. The socks are better in Japan, the shoes are better in Italy, and everything I own with the exception of my computer and my (come to think of it, Japanese) running shoes pales in comparison to what I can find while traveling.

I had to bring it, because otherwise I would have felt unprepared. But when I started traveling, I had to throw it out.

Everything I thought it would be, it wasn’t. Everything I couldn’t have hoped it would be, it was. And I had to be flexible enough to pivot. I looked at my beautiful Bluntstones and realized I would hate dragging them around the world. My cleverly chosen leggings-meet-shapewear are just plain dowdy. It turns out, there’s nice lotion on the road, and it isn’t actually necessary that I smell like Brazil at all times. My sensible purse, with all those sensible pockets, is just plain ugly. And I do not need my hotel room to smell like home.

You will not make those same mistakes, but it’s possible you’ll make different mistakes. And the fastest way to recover from a mistake is to adapt quickly. Envision your cup as already broken, and you’ll enjoy the journey so much more.

That’s what I’ve got.


A few other things to do while you're here:

  • The Emergency Turnaround Clinic (100% FREE!) – A re-release of our “how to survive the recession” class from Back In The Day – no sign-up required
  • The Karma Store – 12 of our products are still on pay-what-you-want, so if you need anything in there, you can still get it.
  • Unlock the IttyBiz Freebie Vault (now featuring the Money Masterclass!)
  • Naomi’s new blog – it’s about how to take care of yourself and the people you care about
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