Living the Dream - Logistics

Note: This piece was originally published over on Working/Not Working's Free Range and I'm proud to be able to bring it to you here as well. They have tons of great stuff - click on over there sometime, and check them out!

One common question I hear is, how do you do it?

The question isn't psychological or metaphorical, but practical. As a professional programmer and writer who dabbles in visual work, how do I live out of a single suitcase?

I'd love to tell you the answer is a magically infinite bag I bartered my soul for in the depths of the Thai jungle, but unfortunately, the answers are simpler and more practical than that.

If you're looking to travel the world and keep working for even a month, here's how to do it.


You don't need a lot. A wonderful truth about every place that's inhabited on earth - is that people live there. Because of that, you can buy pretty much anything you're missing, including tech.

That said, here's the things I'd buy and set up while you're still home.

A laptop

Your personal preference, but make sure it can handle global voltage. I love my macbook pro - it's tough, reasonably life resistant, and just works. It also plays well with my phone, which comes in handy, as you'll see later.

Regardless of what you choose, encrypt it, set a good password, and be smart about where you pull it out. Your laptop is your single most valuable possession, and it's worth a lot in the wrong hands. That goes double if they have access to your data.

A keyboard

If you spend any significant portion of your day pressing down plastic levers to make the screen light up, you're going to be really happy if you brought a proper keyboard. Ridiculous as it is, I travel the world with a giant Microsoft 4000 ergonomic keyboard.

If you spend your day typing, don't scrimp on your primary interface to your computer. Be good to your wrists.

A tablet

I've got an iPad, and dig it. Tablets are great for the road because they give you a mid-size decent computer when you need it, without having to dig out your laptop.

If you've got the right hardware/software combo, they can also double as a second monitor.

I use my iPad with Air Display, and it serves as a fine second monitor. Especially for people who code or do graphic work, the extra screen real estate is killer.

An external HD

Fill half of it with movies, music, or whatever's going to help you chill out when your internet's down. Use the other half for a regular backup of your entire laptop.

If your laptop is stolen (reasonably possible), you don't want to be waiting five weeks for dropbox to download everything to its replacement over your terrible Costa Rican internet connection. Keep a good local backup.

An iPhone

This is the one specific hardware recommendation I'd give. I love me some Android phones. But for international travel, it pays to get the world's most widely known phone. Everyone, everywhere on earth has heard of an iPhone, and every cell company in existence knows what to do with them. Go with the gold standard.

Something tough that locks

I love my Zarges box. It's aluminum, lightweight, German (which is to say impeccably built), and it locks tight. When I'm traveling, it serves as a nearly indestructible suitcase. Once I'm settled, it works well as solid room safe.

Cloth and hard plastic bags can be cut open with a pocket knife. If you can swing it, go with something significantly more tamper-resistant.

ATM card with a chip and no foreign transaction fee

Especially if you're in it for the long haul, doing a little bit of homework up front is going to save you from pissing 3-5% of your money down the drain.

Get your checking account set up with a bank that doesn't charge foreign transaction fees for ATM withdrawals, provides a card with a chip, and has good customer service.

In many places, this card will be how you pay for rent, food, and transportation. Get a good one.

Two credit cards with chips and no foreign transaction fees

If you'll be in places that accept credit cards, getting a good pair with no foreign fees will save you a ton of cash. Credit cards are also significantly better protected for fraud, and more responsive than banks when issues come up.

Rule of thumb:

  • If you need cash, use your ATM card.
  • For everything else, use your credit card.

Have a spare card for emergencies, and to handle the times when you're locked out of your accounts. Because you will get locked out.

Your bank's phone numbers, on a piece of paper

At some point, you'll need to call your bank to assure them that yes, you know there was a charge in Zimbabwe last week, and one in Guatemala this week, and yes, both of those are legit, and pretty please, can they unblock your card because you're standing in a supermarket with a cartful of groceries and no way to pay for them.

On a related note, give all of your card companies a call and tell them your travel plans. It won't prevent them from fraud-locking your cards, but it will mean they fraud-lock less often.

A power strip

This isn't an absolute must have, but if I had to pick one nice-to-have piece of tech, it'd be these little Belkin power strips. They handle 110 and 220, and provide two fast USB charging ports. They mean that at home, in airports, and wherever, I never have to worry about only having one outlet.


A VPN program (I recommend TunnelBear) lets your laptop, phone, and tablet securely pretend to be from another country. There are places in the world where this is really critical, and some where it's just nice. Here's the lay of the land.

Getting around filtered internet. If you're going to live somewhere where the government filters or monitors internet usage, a VPN is a must. The last thing you want is to talk to the officials in a place where you may not speak the language on why you were accessing illegal materials.

Don't let the "but I don't look at anything sketchy online" mindset lull you to complacency. Depending on where you live, "illegal content" can be much more innocuous than you think. Like Wikipedia.

Safe connection on sketchy Wifi A VPN is like a condom for the sketchy wifis you'll inevitably find yourself on. Without one, you're at the whims of the person running the corner cafe and everyone else on their network. If you're doing banking or any kind of online purchasing, you're going to want an extra layer of protection.

Netflix! The BBC! The NBA! The final really lovely thing you get with a VPN is that you can pretend to be wherever is most useful to you at the moment.

Want to watch Orange is the New Black? Set your VPN to the USA, and fire up Netflix. Craving the latest Dr. Who? Set your VPN to the UK, and open up the BBC's site. There are even sports leagues (the NBA comes to mind) who offer better, cheaper access to people living particular countries. With your trusty VPN, you can be "from" those places, and have truly global access.

Install before you go Finally, make sure you've got your VPN installed before you leave. As you might suspect, the places who don't want you to see the whole internet also don't want you to download software to get around their filters. Install and test your VPN while you've still got unrestricted access.

Internet Access

The sweet nectar of internet is critical for most of us who work remotely. Here's everything you need to know to get yourself set up.

Stay somewhere with good Wifi (if you can).

Airbnbs are typically better about this than most other places, since their owners are relatively high-tech. I'd start there when looking. You can definitely get by without wifi, but if you have large file uploads or downloads, using anything besides a proper wifi connection will get expensive, quick.

Find a spot with good, unlimited wifi, or be prepared to pay.

Learn to tether your phone.

Having a backup source of internet will serve you well when things go sideways, as well as the days where you want to work from the beach.

In short, the best path is to get an iPhone, buy a local sim card, and buy a prepaid monthly data plan.

The exact method for doing this will vary from country to country, but it's a normal thing in every place, and everywhere you go, the employee at the cell phone store will know how to set up your iPhone.

If you've gone all-in on the apple ecosystem, tethering your phone is easy. Go to settings, cell, and turn on tethering. Then, on your laptop, pick your iPhone from the wifi list. Simple, done, and you've got internet that will go with you.

Your Company and Clients

Learning how to work and communicate remotely (especially if you're the first to do it) is unmistakably a challenge. However, there are a few quick tips that can make life much easier.

Know your time difference

Time differences are one of the hardest logistical challenges of remote work. For most collaborative teams, having a window of at least 3 hours of overlap is critical for good communication and shared progress.

Before you head off, know the time zone of your destination, and make a plan with your team on when you'll find that shared window.

This will allow you to have a good frame for your workday when you land, and more critically, help put your company at ease. See, they're nervous.

Set Expectations

Having an employee or contractor wander off to the far reaches of the world is a scary, scary thing. Most companies want their employees to be happy and fulfilled, and the idea of remote work makes a lot of sense - in theory.

But in practice, for a lot of companies, it's a laundry list of unknowns and impossibilities.

I've done this at a number of places, and the biggest key to success is to talk through, plan, and set expectations about how communication and deliverables are going to happen.

If you're the one heading out, your boss and colleagues are likely to have a hundred nervous questions running around in their heads. Set aside some time to get those questions out, and collaboratively figure out answers.

Almost always, they want it to work as much as you do. They just don't want to be stuck if their star employee runs off and never comes back. Establishing baselines for what everyone should expect goes a long way toward easing tension.

Communication Culture

The other big change that comes with the distance and the time shifts is that communication patterns and culture are likely to need some tweaks.

Unless you already work at a fully remote company, it's likely that a decent bit of collaboration happens informally in the office.

When you're remote, your in-office colleagues are going to have to take the extra step of finding a computer, pinging you, and firing up a video chat to keep you looped in.

This is not an insignificant extra effort. Making sure to talk about it beforehand and acknowledge it when it happens greatly helps to build this behavior.

Finally, for many remote teams, an asynchronous communication platform like Slack or Hipchat works wonders. It lets people catch up when they have time, work on their own schedules, and stay looped in.

It takes time to build these patterns as norms for a company culture, but for a long-term remote work setup, you'll need them to succeed.


You've got a few options for where to stay on your travels: hotels, hostels, Airbnb-type places, or renting an apartment. All have their pluses and minuses. Here's the rundown.


To me, this is the best-of-breed solution at the present. It's more expensive than a hostel or renting a local apartment, but you get more. You can find a nice place with good amenities, kitchenware, and good wifi for a decent cost. You can also typically find places with a couple of distinct spaces - great for having a separate space for work and relaxing.

Airbnbs also tend to be in interesting areas of town, and run by people who have travelled a bit and get it. Start here.

One note of caution - you typically get what you pay for. Stick to the mid and upper end of the price range for an area if you're looking to avoid cockroaches and have reliable internet.

A note on VRBO, couchsurfing and similar: Some people love and swear by each of these services. I'm not one of them. Find what works for you.


These bring to mind earthy-smelling backpackers and big rooms with shared cots. It's not an unfair assessment. There are private rooms available at many hostels these days, but hostels are also the most likely of your living options for something to be stolen. Unless it's specifically your scene, I'd avoid them.


If you can afford them, hotels can have the nicest amenities and having someone take care of the basics like cleaning and laundry can be lovely.

The biggest challenge from a remote-work perspective is finding one where you've got a good working space.

They also never quite feel like home, at least to me. If you want to feel settled in, you're probably better off with a local rental or an Airbnb.

Rent like a local

With a local rental, you just figure out how apartments are listed locally, go find one you like, negotiate rent, and move in. For longer stays, you're going to get the most space for the least cost, and the most authentic connection to a place.

One big gotcha: I'd only recommend local rental if you're at least decently fluent in the language where you're moving. Renting an apartment comes with all sorts of details wherever you are, and they'll be on you to handle. Things like how to pay electricity, water, and utilities. How to get internet installed. Who to call if a pipe breaks, and how to tell them what's broken.

You'll need good language skills to handle the stuff that comes with a local rental - but if your language skills are solid and you're sticking around a while, there's no better or cheaper way to really settle in.


Health is one of those big, back-of-the-mind scary monsters in international travel. What if I get sick? Should I bring medicine in case my migraines flare up? Or my bunions?

My advice from having lived out here is simple.

If you have an reasonably frequent medical condition that requires medicine and you know what works for you (like allergies, for instance,) bring enough to cover your stay.

Don't worry about anything else. Don't bring a medicine cabinet of what if's.

The reason is simple - if the internet's good enough for you to work, there'll be a pharmacy, and things in the pharmacy to help. I promise.

My lone exception: do take a water filter if your travels will take you to somewhere without drinkable tap water. I've lived by my Camelbak UV filter, and love it. Find what works for you - but do bring something to easily supply you with clean water.

The Psychology of International Living

There are two final mental hurdles to living all over the world: learning languages, and finding the social support you need.

Learning Languages

There is an internet full of great resources. Definitely do some digging.

That said, here are my top two tips:

  1. If you're going to have a go at learning a new language, read Fluent in 3 months. It's short, effective, and packed with the best techniques I've seen anywhere for language acquisition.

  2. Buy the best dictionary app you can find for your phone. You want something that works offline, lets you look up phrases, see conjugations, and ideally gives example sentences. For most languages, there's one really exceptional app. It's rarely free. Buy it.
    (Here are the best ones for Thai and Spanish.)

Smartphones make learning a language a radically different process, for good and bad. But when you absolutely need to communicate with someone, having a dictionary you can both use is invaluable.

Social Support

Know thyself. Are you an introvert? An extrovert? What do you need to be recharged?

When you hit the road, all the social supports you've slowly and unconsciously built over the years are going to be gone. Instead, you'll need to consciously create new support circles every time you land - and it do it, you need to know what you need.

I'm an introvert - it's a complete pain in the ass for business networking, but mighty convenient for traveling. All I really need to recharge is a quiet space with nobody around. In traveling, that comes by default.

But I also know extroverts who successfully travel all over the world. When they land, they consciously invest time into finding a few new regular social activities, and places where they can go to be surrounded by people.

Social support is something we mostly take for granted in a rooted life - but it's a critical part of the human experience, and drastically affects our sanity.

Especially if you're in for the long haul, take some time and think about what your needs are, and how you'll get them on a random Tuesday in Prague when you don't know anyone. That little bit of planning will make all the difference.

That's What I Know

That's everything I know from my time living here on the road. If you're thinking of giving it a go, feel free to reach out with any questions. I'm happy to help.

I'm also still out here, traveling, learning, and sharing what I find - if you're interested in following along, I have a pretty lovely letter I send out.

Bon Voyage!