Start Planning Your Adventure: The Ultimate FAQ for Nomads

27 of your most common questions on working remotely and this nomadic lifestyle, answered.


Hi, I'm Stephanie.

A nomad. Lifter. Foodie. Geek.

I spend my days working out, writing, and living out of different cities around the world. From Paris to London to Tokyo.

Perhaps you want to do something similar, but don't know where to start. I was clueless too; and, like you, came across the tired advice of "follow your passion" time and time again. Oh, lawd.

"Following your passion", taking risks, conquering your fears, etc...they play a minor role in your adventure.

I don’t believe you need to be exploding with wealth or penny-pinching to embark on or sustain this nomadic lifestyle either.

You need a plan, not a pocket full of dreams and a "welp, it'll all somehow work out!" attitude.

You also need to think about emotional and physical health, productivity, and your money very differently and pragmatically. And a bit of guts.

Still, I understand you have a lot of questions about the nomad life:

What do I do with all of my stuff?

How do I find work?

Do I need travel visas or insurance?

What should my budget look like?

I’ve collected the most common questions I get and answered them with my insight and experiences. I won’t claim that my methods are optimal, but they'll give you a fair reference point. Chances are good that your burning question has been addressed. 

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I’m a freelance editor and professional writer with a stable number of clients. That’s my advantage from having been writing and editing professionally over the years.

The 21st century allows all of my work to be done online, as long as I have my trusty laptop and reliable internet. (But when the internet is seriously being a jerk, it's all I can do to not break down and sob uncontrollably.) Since 90% of what I do is call, write, and edit, I really just need access to email, Skype, and Google Docs.

I’ve also set up most of my payment terms and systems so that I can be paid in U.S. dollars, electronically, wherever I am. Services like Lystable and PayPal (if we go a little more old school) make it pretty easy, but most of my clients have their preferred system. Occasionally, people remember that paper checks still exist. If a client sends me one, I am fortunate enough to have a family member who can take care of depositing it in the bank for me (usually by physically going to the bank or taking a photo of it via remote deposits).

Beyond finding a way to make money remotely, I encourage you to go back to the previous questions to make sure you don't overlook the small details like your mail, automating statements and payments, and what to do with your car insurance. But here's another that I see a lot of people ignore:


Get rid of your debt first. Seriously.

A big part of the reason this lifestyle is possible for me is that I had already paid off my debt (it just worked out that way) and have someone taking care of my property. I highly recommend holding off on that glamorous, world-traveling lifestyle until you’ve paid off any major debt. This includes your school loans, any massive credit card debt, a car, or a house (although the house can be tricky).

Whatever your debt is, you don’t want to have it looming over you and use "traveling the world to find your passion" as a stupid and short-lived excuse to escape it. 

Getting rid of student loans, for instance, is already hard enough, so if you’re out prancing on the beaches of Maui or the countryside vineyards of Nice, it gets that much harder. Then there’s interest to consider. And if you have any desire to save more money (and let’s face it, who doesn’t?), you’d be in a much better position if you make bigger monthly payments to minimize the interest as much as possible. Over the long term, that’s thousands of dollars saved if you have to pay for loans of $20,000 and more.

For savvy personal finance stuff (which, hey, still applies to people who travel), I highly recommend you check out personal finance expert Ramit Sethi, my buddy and fellow Lifehacker writer Kristin Wong, and Mr. Money Mustache. All of these people preach very, very smart, non-B.S. matters on living the best and richest life you can (without actually needing to be rich, in the traditional sense).

Paying off your loan before you screw off on planet Earth is basically me encouraging you to "front-load" the work. That is, do all of the difficult crap in the very beginning. When you front-load taking care of your loans and automating important things before you leave, you won't have to deal with the hot mess later. You'll be glad you did.

I mentioned earlier that The Earth Awaits and NomadList can give you a bird’s-eye view of how far your budget can go. I also recommend using Budget Your Trip to establish a fair baseline, and then pad that with an extra 15-20%. That way, you plan to have a bit of cushion if you end up traveling a bit fast and loose without ending up in dire situations where you’re missing a shoe and wondering if the nice family that took you in is going to harvest your organs for beer money.

This strategy, of course, assumes that your money situation stays static the whole time. Working and traveling together change your money situation, where you just track your monthly income and expenses. I use Mint to monitor my cash flow, but I’ve heard of others using Wave or TrailWallet.

All in all, how much you need for travel is something only you can answer, not a Magic 8-ball or anyone else. And truth be told, it’s your spending habits and your mindset about money that’ll run the show. Part of that, I believe, is understanding the difference between being frugal and being cheap.

Frugal and cheap are not the same thing.

They’re often used interchangeably, but they’re galaxies apart in meaning. This is a lesson that took me far too long to learn, but once I did I’ve been able to travel better and enrich my traveling experiences (without paying out the wazoo, of course). The most important distinction among frugality and cheapness is cost versus value.

Cost is a hard number; it’s measurable. The number is high or it’s low. Value, on the other hand, is subjective, calculated based on, essentially, your long-term happiness level. You can argue, too, that the cost of something contributes to that happiness level, but it’s not the only measure.

Cheap people often care about the direct cost of something, whereas frugal people prioritize the value of something. That means a cheap person only cares about getting the lowest price, no matter if the quality of the item hurts them, or worse, costs them more money down the road. A frugal person would ideally like to keep costs low, but are willing to flex their purse strings for something that is important to them.

With frugality, it comes down to picking and choosing what to spend your money on. For example, in my article on where to stay in Tokyo, I suggested that you spend extra money to stay more central out of convenience and in order to fully appreciate Tokyo’s uniquely manic atmosphere; but also, in the long run you save on transportation costs and a whole lot of frustration and hassle.

Cost versus value.

Part of the fun of traveling is spending money in ways that enhance your experiences, but only if it makes sense and it’s something you truly care about. One question I often ask myself is, If I came across this opportunity back home, where the novelty of being in another country is less influential, would I still spend this amount of money on this thing? This is kind of my test to see if I truly care about that thing, or if I’m just wearing “travel goggles” (like beer goggles, but for travel, you see?).

It depends on your work situation.

My clients expect me to produce and deliver stuff every single week, in addition to other projects that are a bit more irregular but still require a lot of my time every week. In essence, I am juggling full-time work while traveling, which is actually a lot harder than it sounds. Some days I’m so busy working that I’m unable to leave the house to explore the fantastical, foreign world outside my window. That has led to many episodes of anxiety-filled freak-outs.

It took a long time, but I’ve finally learned to identify important and urgent work, hire help, and generally be much more protective of my time. Much of finding the balance between work and travel is being able to ruthlessly prioritize what you really need to focus your attention on and what can be shoved to the next day, without feeling guilty. You can read about some of my work habits here, but you’ll notice the overriding theme is to create a system that conserves mental energy as much as possible.

In our day to day, there are three scarce resources: time, money, and energy. I believe that as long as you have energy you can figure out how to shuffle your time, and in turn, convert that time into money. But the very nature of traveling--making new, exciting discoveries and getting high off novelty--make up the lion’s share of your energy and turns staying productive into a real challenge.

When you’re somewhere new and unfamiliar, everything requires conscious effort and thought for even the most mundane tasks: where and how to find coffee; where to do laundry and how often; how to not look like a jackass in front of locals; or should you check out the mom ‘n’ pops restaurant down the street or check out that highly reviewed place on TripAdvisor?

The most powerful counter to a never-ending series of exhausting questions every day is to establish a routine: know what you’re going to do and what you're going to work on and when, without batting an eyelid. Ironically, we tend to give our same-y routines crap until unfamiliar customs and environments throw you into perpetual mental Tetris.

Whenever I head somewhere new, I spend at least the first couple of days scoping out my surroundings to nail down a new routine. The most important things I look out for are coffee shops (outlets, Wi-Fi, good coffee and environment), public transportation, grocery stores, gyms or parks for working out, and quick sources of food.

I’ve always been sort of a fitness junkie, to the point of working out five times a week, without fail, and perfectly nailing my 140 grams of protein each and every day. Traditional gym workouts were life. When I started traveling, I worked out five or six days a week with my suspension trainers and squeezed in a gym session whenever I could find one.

But it was difficult to stick to a very rigid regimen because of the changing physical environment, which affected my routine, and availability of foods.

I knew that I had to adapt.

These days I still value fitness, but instead of obsessing over how many days I work out, with a non-negotiable number of sets and reps, and hitting my nutrition and protein needs perfectly, I tell myself to settle for “good enough.” It wasn’t easy for me to accept at first. Eventually, my white-knuckled grip on my fitness loosened when I finally just accepted that my mental energy is like a tree branch: it has to bend from repeated, daily invisible forces.

I’ve decided that forcing my body to be a textbook specimen isn’t my priority (or very realistic) any more. That said, working out is still something I strive to do regularly to keep myself in shape and strong. I believe, after all, that the physical strength and discipline I’ve built over the years in the gym are why I can travel as independently as I do. Plus, regular workouts keep my focus and concentration sharp, help me get better sleep, and overall let me feel accomplished and grounded in an otherwise constantly moving lifestyle.

During my travels, I was able to walk everywhere, go hiking, join communities for Frisbee and other fun sports, rock climb, and any other activity I can find. For strength training, I did bodyweight programs and work out on my travel-friendly suspension trainers, which are a pair of straps with handles.

All of this actually isn’t very different from what I do at home, but I will say that my intensity has dialed down.

When planning for a long-term trip, the most important couple of first steps are to check that country’s visa requirements, book your flight, and set up accommodations that you won’t regret. (If we’re being honest here, I also check the absolute best things to eat.)

If you have a U.S. passport, you can enter many countries without prior paperwork, but you should still check before you go. For more on visa requirements, check the next question.

For booking flights, there are a ton of “travel hacks” to find incredible deals on flights. Travel-hacking is essentially about finding little loopholes to game the system and using credit cards to rack up rewards to get things for cheap or free. Here at FY!S I don’t focus on this hacking aspect, as there are many other sites and bloggers who do a much better job of it than I. Instead, I like to keep it pretty simple.

Because a lot of the best deals are often so spontaneous and only stick around for a couple of hours, flexibility with your travel dates is the best way to fly on the cheap. I’ve signed up for Airfarewatchdog, which helps me stay on top of cheap airfare.

When I start searching for flights, I start with Kayak or Skyscanner. They’re both great aggregators of deals and flight information from around the web. They give you an idea of the baseline prices for around the time you want to leave. If you want to have more control over your flight, check ITA’s Matrix, a free tool that gives you a more detailed breakdown of the flight's itinerary. More experienced travelers may use ExpertFlyer.

The point is to not book directly from these sites, only research. Because once you find cheap airfare, you'd generally benefit more by going on that airline’s website to find the same flight. Oftentimes, if you tweak the flight information there for different dates, currency (if you’re flying internationally), and airports, you might strike some real gold. If I’m already overseas, I check sites like Momondo and Mobissimo, which tend to search foreign sites better.

And finally, for booking accommodations, I typically stick with Airbnb because it’s currently used worldwide, easy to track my expenses and trips, and Airbnb’s policies tend to be a lot more comprehensive and safer, relative to other similar services. For more on using Airbnb to live around the world, check out my guide here.

...and a ton more answers to a ton more questions that probably wouldn't cross your mind until you read it and go "Oh, right.

Read all 47 pages of my guide to 27 of the most common questions about this kind of remote work-travel lifestyle and my experiences with making it sustainable and fulfilling. From getting started to the logistics of planning to the day to day, it's all in a convenient and downloadable PDF that's absolutely free.

If you're ready to say "fuck yes!" with me, enter your email in the box below and we'll continue on this journey together.

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