How Can I Afford to Travel All the Time? Remote Work, Relaxed Pacing, and Not Giving a F#ck

When you’re traveling and you meet someone and speak to them for more than a few words, they almost inevitably ask you when you’re heading home, the unspoken understanding that “heading home” is a phrase burdened with luggage like work, cleaning house, and all the other mendacities of day to day living. The assumption being that wherever you are you can’t be staying for more than a few days or a few weeks before Things Must Be Attended To.

I never have a good answer for this. Well, let me amend that. The answer is at best good and at worst somewhat garbled and nonsensical. It’s difficult to weave a cohesive narrative through a list of so many seemingly disparate destinations.

The idea of traveling constantly – all the time, no home, or no home but the temporary ones you construct on the road (blanket forts, metaphorically speaking) – is a concept that has enthralled and unsettled many, but the How’s behind it make it seem impossible.

So at some point most people end up asking – how do you afford to travel all the time? Or some version of that question.

Everyone has their own reason it seems impossible. The most common two are work and family. From there people worry about details like what to do with the home they have and how will they find a home, how can you actually get everything you need into a suitcase, what about the languages, etc., etc.

The Disembarked lifestyle comes in many forms. The weirdos who can’t live any other way work it out, think of some hustle or another. Either they’re one of the much-discussed Digital Nomads, or they’re adept at cobbling a living together wherever they go. Or else they’re just rich. Whatever the case, they make it work.

This is how I do it.

The Work – It Ties It All Together

I’ve been a freelance writer for nearly a decade. That doesn’t mean that I’ve been traveling for all of that time, as the first several years barely put tuna on the table. But eventually I snagged enough balloon strings to give me some buoyancy. My work has carried me places, is what I’m saying.

My work is a coin with two sides. On one, you have the publication writing – articles on travel, fitness, music, and such – and on the other you have copywriting and brand strategy and the like.

And then there’s all the work I’m not getting paid for, the work I do for myself like the book and this blog. I’m not sure where it fits into this coin metaphor.

Anyways, the work can be done anywhere, and – though I sometimes have to jump on phone meetings at all hours of the night because of Time Zone Madness – the work can usually be done whenever, as long as it gets done, meaning I can slam through a ton of it all at once, then take large batches of time off to see wherever and whatever.

This presents an interesting opportunity – the more places I travel, the more I have to write about, and the more articles I can sell. So it’s kind of a self-perpetuating machine. A real snake-eating-its-own-tail situation.

The Style of Travel – It’s Paced

When a lot of people think of traveling the world, it means hopping trains and planes constantly and being in a new place every handful of days.

I do that from time to time. The upside is that you get to see and do a lot all at once, and there’s a special rush that you get from the frenzy of it all. But it has two downsides – it’s an expensive way to live, and it makes hitting work deadlines significantly more challenging.

My solution involves pacing. I slow things down.

For example, I’m in Puerto Escondido now for two months, then Belgrade for a month, then Paris for nearly three months, then a brief stopover in Italy before I’ll have to leave Europe due to Visa Madness. From there I don’t know. Ireland? Morocco? India? Whatever the case, I have to be in Vietnam in November, where I’ll be joined by my brother for a month.

I am a proponent of this variety of travel for several reasons:

Argument 1: You spend less time and money on the actual process of getting to and from different places. Plane tickets and time off work and shitty airport food and taxis and metro tickets and so forth add up fast.

Argument 2: You can rent long-term, which is much cheaper than jumping from place to place all the time. Most Airbnb hosts give substantial discounts when you rent for over a month. The nightly rate might cost you in a week or ten days the same amount you’d pay for a month or more.

Argument 3: You have a kitchen where you can cook your own food. Huge savings compared against eating out all the time.

Argument 4: You actually get to know a place. It’s impossible to learn the deeper secrets of a destination when you’re only there for a few days here and there. When you spend a month or two in a place you get a more intimate experience. You learn which grocery stores are the best. You get to know the people. You work your way into the local pace of things. You learn where to get the best tapas.

Argument 5: You get a break from the fucking road. Being on the move all the time is exhilarating, but the stress and rigors and emotional expense that comes from the ongoing sense of disconnection and lack of community are taxing. Sometimes you need to slow things down and get a breather.

I tend to plan things in bursts. Four to six months of relative stability in two or three different places, then a month or so rush of Travel Madness before settling back in someplace new.

My Stuff – I Don’t Have Much (Or I’ll Get It Where I’m Going)

I’ve lived out of a variety of bags over the years and have trimmed down my load with each progressive bout of travel. Currently I’m carrying and rolling an Osprey Ozone 22 Convertible. It’s a medium-sized carry-on suitcase (w/ wheels and backpack straps) that has a detachable day pack/carry-on zipped to it. It holds all the essentials (a couple of outfits, workout cloths and running shoes, laptop, Kindle, camera, phone and their attendant cords and electronic gadgetry, toiletry kit, a smattering of other conveniences), but I certainly don’t travel with much.

Everything else I own – which could never properly fill out a one bedroom apartment – is awaiting my conceptual resettling in a storage unit north of Seattle.

Sometimes I bring a guitar.

But in general I don’t bring much, and I usually have more than I actually end up needing. Every time I head back out, I leave more things behind.

And then once I’ve arrive in my new destination, if there are things I need I buy them. Another benefit to staying in one place for a longer stint is that your temporary stability means you can gear up as necessary.

For me this has meant different things in different places. Sometimes you need a fan, or an extra blanket. Usually I get a yoga mat and some sort of weight, either a kettlebell or dumbbell. When I move on I leave them in the apartment. Who doesn’t want a nice piece of workout equipment at their Airbnb?

On that note, the paced travel style also means I can join a gym. If you’re traveling fast and want to hit up a gym, every once in a while you’ll find a place that offers day or week passes at a jacked up rate, but you can’t depend on that. Just about every city, however, has a gym that offers monthly options.

The Places – I Go Where Money Stretches

Some places cost a lot more than others.

Puerto Escondido is inexpensive both in terms of exchange rates and the general cost of living compared to more popular spots like Cancun. Spain is on the Euro which doesn’t exchange in our favor, but its cost of living is low, especially once you get out of Barcelona and Madrid.

I tend to spend my longer stretches in places like these. This allows me to save up for the random eruptions of fast-paced, high-priced Travel Madness.

The Languages – Fuck It, Who Cares?

I have decent Spanish, so I get by fine in those countries. My French is extremely limited, however, so France is a bit rockier. And before long I’ll be in Serbia, Italy, Vietnam, and more, and I don’t know anything about those languages. (Not true – I know that ziveli means cheers in Serbian, and o means umbrella in Vietnamese, and I’ve been told that if I just speak Spanish with a French accent the Italians will get it…)

But fuck it, who cares?

Most communication is based on body language and tone and such anyways. People are people, and they figure out how to communicate. And the fact is that, in a pinch, someone in the room usually speaks English.

I’ve had many conversations that stagger between a smattering of words from English, Spanish, French, German, and so forth all within a single sentence. These are often accompanied by sound effects and incomprehensible gestures that are intended to be clarifying. One way or another, it works.

Before I go to a place, I try to learn a few of the basics:

• Please
• Thank you
• Where is….?
• How much?
• Check please
• What is your name? My name is….
• Would you like to have a drink with me?
• No, thank you
• Your place or mine?
• This taxi is driving in circles!

You know – the things you absolutely need to get by.