Start Planning Your Adventure: The Ultimate FAQ for Nomads

"Following your passion", taking risks, conquering your fears, etc...they play a small 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. You do need guts and to think about emotional and physical health, productivity, and your money very differently and pragmatically.

Still, there are a lot of questions about the nomad life. 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 help you with a fair reference point. Chances are good that your burning question has been addressed. 

This page is a sampling of what you'll get in my full PDF guide that you can get for free when you enter your email address in the box below. 

Also, in the spirit of full transparency, I want to let you know that some links to items in the guide are affiliate links. These are items that I trust or have used myself and are helpful recommendations to you. Clicking on these links does not cost you extra; I just earn a small commission if you choose to buy.

Click on the “+” sign next to each question to expand my answer.

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Ground Zero: Getting Started on Nomading

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:

Debt.

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.

Most digital nomads have skills that can be leveraged in the tech world. They're writers (such as myself), graphic designers, coders, marketing consultants, or consultants of some type. You can also create your own online business. Those are the most common types of work that easily come to mind.

If you don't have those skills already, all of this might sound like an elusive, pie-in-the-sky dream. In reality, you only need to build a skill set that allows you to do any work online. Or more likely, you already are good at something, but didn’t realize you can actually make money off it. Maybe you’re really good at playing poker. Some of my friends are successful online poker players and they do it at home anyway. You can also be a virtual assistant. Or an online personal trainer. Or a speaking coach.

Modern day has amplified the number of possibilities that the choices can be both a blessing and a curse. The biggest barrier is you and the mental walls that have predetermined what is possible and what isn't. And oftentimes these walls are a lie.

There’s no “best” work for digital nomads. The best work obviously is the one that lets you do what you do, free from financial worry. It’s the kind that you know if one or two clients slipped away from you, you know you can still get more.

If you want a "quick" means of escape, teaching English in Asia or Latin America is one way to get paid to go to a country and live there. The pay is low and the work can be awfully boring, but I've been told that the experiences as a whole can be eye-opening.

Word of caution: freelancing or entrepreneurship isn’t for everyone. None of it is passive work. At least certainly not in the beginning. All those promises of “passive income” takes a crap ton of long hours and aggressive work before anything becomes “passive.” 

Ah, the million-dollar question, and I’m going to answer this in a rather roundabout way.

I’m a freelance professional writer. Most people have preconceived notions about what that means, which is understandable. By nature, freelancing for anyone can be very erratic. Some months you’re flush with clients and cash, but other months you might be treading on scorched earth.

It’s possible, however, to do really well as a freelancer, like well-into-the-six-figures well. But just like anything, it’s not passive work and requires the right attitude and mindset.

And a network.

Over the years, I’ve built a specific skill set beyond writing and have leveraged my positions at various companies to expand my network--mostly made up of people I call my close friends, but also many, many, many more whom I have very loose but still important relationships with.

“Your network is your net worth” is an oft-repeated quote (and the name of a book) in the entrepreneur/business world, and while you may roll your eyes at it, it's not a load of crock. Without the people who have helped me, I would not be where I am today. At the same time, without being proactive enough to cultivate my relationships with them in a human and authentic way, I would not have my network.

Networking gets a really bad rap. It sounds very matter-of-fact and business-like, but note the difference: There’s “networking”--the schmoozing, the shuffling of business cards, the “What can this person do for me?” mindset--and then there’s creating real human connections, which starts with, “How can I create value for someone else?”

The other component to that is that you should aim to give a gazillion times more value than you ever hope the other person can reciprocate. This wasn’t easy for me. I have only-child syndrome, which is all about me. One of my good friends, Sol Orwell, has been hammering into my head to basically “do or say things to people that you would want others to do or say to you.”

This means that if you find a great article or book, think about someone else who would enjoy or benefit from it. Regularly wish others well on Facebook or other forms of messaging. Tell someone you're thinking about them. It just feels good to make someone else feel good.

As a result, I am very grateful to say that I have steady clients and customers who actually want to work with me every week. Through them, I am able to meet more and more people and talk about fitness, beer, donuts, video games, or anything.

I found Marie Kondo’s book, The Life-Changing Magic of Tidying Up: The Japanese Art of Decluttering and Organizing, to be extremely helpful with teaching me to detach my emotions from physical objects. There was one particularly effective idea that kind of makes you seem loony at first. It combines sunk cost and expressing gratitude for how the item has already helped you--whether it's a shirt, a couch, or a spatula.

In economics, sunk cost is the idea that you’ve already paid for something (with money, time, energy, or all of the above) and no amount of wishing can return those costs to you. The natural inclination for any time we fork over our own cash is, we cling to this object, hoping to squeeze every ounce of value from it and get our money's worth. 

At a certain point, however, it’s already more than served its purpose or provided the value or happiness--however brief--you wanted out of it. So, Kondo suggests you be a weirdo and tell the item, right before discarding it, something like “Thank you for helping me and my happiness. You may go now.”

And strangely, this acknowledgment just makes it easier to discard it. Put it another way, she argues that if you do decide to hang onto the item but put it in storage indefinitely, that's a fate worse than dumping it. Not to mention a waste of space.

Material objects should always, always enhance your life or help you remove a negative from your life. If it starts to feel like a burden or is kept because of some sentimental attachment, then maybe it’s time to look at it as having already fulfilled its duty. Then chuck it and never look back.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

Travel Planning & Logistics

I pick a place out of a special Sorting Hat. 

Nah, just kidding, though that would be cool, wouldn't it?!

In truth, where you want to go is a question that only you can answer. This is based on you and your needs, though I know a lot of people choose destinations based on cheap airfare and what their budget allows. So allow me talk a little more about my own process.

I’m a solo female traveler who needs internet to work and loves to eat and work out. Based on these needs and wants, I immediately have a couple of absolute necessities: safety (is the place relatively safe for solo travelers and travelers in general?) and reliable internet (how easily can I find internet and is it fast enough for video calls?).

Safety and internet, then, are no-brainers for me. 

Once those needs are met, my secondary needs are awesome food and places to work out. They’re less of a big deal because I’m an adventurous eater and can rejigger any food to fit my health and emotional needs. I can also work out anywhere by either finding gyms or getting creative with bodyweight and other types of workouts (I'll cover this in the next section).

If the place has a somewhat developed public transportation infrastructure and nice weather, that’s a bonus!

In the very beginning, I selected places that I’ve always wanted to go, and to an extent, I still do. After all, any bucket-list places usually translate to big cities that are well worn by other tourists and have decent internet. Priorities and preferences can change over time, and that's okay.

Chances are, you probably already know where you want to go, but finances perhaps might be the limiting factor. You just don’t know for sure unless you do the proper research, so here are a couple of excellent resources to help you build a better planning framework for any long-term stay.

  1. Nomad List: You can customize your search according to your preferences, including the month of travel, your monthly expenses, if it’s family friendly, if you want to be near a beach or mountains, and so on. It gives you a quick yet comprehensive overview of the place you want to visit.
  2. The Earth Awaits: The Earth Awaits is similar to Nomad List, but it includes other categories, like lifestyle, pollution, crime rate, and attitudes about race and LGBTQ community, that paint a real, clearer picture of your finances and quality of living. The basic search is free to use, but you can choose to pay a monthly subscription to access their more advanced options, which may be helpful if you’re researching school information for studying abroad.

Visa requirements depend on your nationality.

I never realized it before, but only after my recent travel had I learned to be very grateful for my U.S. passport. It allows me to enter many countries on a 90-day visitor’s visa without much hassle. (Canadian passport-holders can look here.) If you have a passport from a third-world country, it’s possible to travel well (Blogger I Am Aileen talks in-depth about that here). There are plenty of exceptions even for U.S. passport-holders, however, so it’d be smart to look into that country’s visa requirements before you head there.

Project Visa and IATA’s website are both great resources that easily help you make heads or tails of visas based on your nationality. You just plug your destination and associating information and it’ll tell you what you need to know.

Real talk: If you are looking for the minimalist way to travel, I am not the best person to model after.

I never understood those people who manage to stuff their belongings for the next several months in a backpacking bag. It gets so bulky and unwieldy and makes things really awkward when you have to navigate through crowded streets, like those in Tokyo. Also, I am, admittedly, a bit of a high-maintenance traveler.

As a kid, my mom had hammered into me a very elaborate skincare routine, which is important to me, and so I have a small bag dedicated to just my cosmetics. Yes, I’ve already downgraded the size of the bottles and skipped over extraneous steps in the routine. But it’s not just skincare. I also bring my own Aeropress coffee maker and Hario portable grinder. Because coffee. Then I have one or two workout outfits, my travel-friendly workout shoes, and suspension trainers for my fitness.

What I’m trying to say here is, I pack things that other travelers may simply ditch or scoff at. But I put up with them because they’re that important to me. When you pack, there are a couple of questions you want to ask yourself:

  • Are your clothes versatile enough to help you comfortably adapt to the changing seasons and climates?
  • Can you ditch your stuff if needed? Similarly, are there certain things you can just buy at your destination?
  • What are my priorities and “bits of home” that I can bring with me?
  • If I bring these things, how can I reduce my overall packing weight?

That third question helps keep my homesickness in check. Whenever I made coffee wherever I was, the smell of my coffee brewing would be this uncanny reminder of home.

When I got ready for my first long-term trip, I was initially flummoxed by how to pack for mildly humid weather, snowy winter, and then a pleasant spring--three very different climates! The answer was layers and packing cubes. I had made many mistakes in packing the first time around, and in the end, when spring (and then summer) came, I had to ship my winter things back home.

In short, bring at least one rain jacket, a down jacket, and many different layers (thermals, long sleeves, button-ups, hoodies, etc.) if you’re going to be traveling through a winter season. Here’s a handy packing list for you to reference for your own long-term multi-season packing trip.

My packing checklist:

Essentials

  • Chase Sapphire Reserve credit card
  • Charles Schwab ATM card
  • Passport
  • Sleeping mask
  • Pack of earplugs
  • Small medical kit that includes band-aids, antibiotics, ibuprofen, hand sanitizer, hydrocortisone (for skin breakouts)

Clothing

  • 4 t-shirts
  • 8-10 pairs of underwear
  • 2 regular bras
  • 2 sports bras
  • 1-2 nicer shirts/blouses
  • 1 rain jacket
  • 1 down jacket
  • 1-2 long-sleeve shirts
  • 1 hoodie
  • 2 moisture-wicking workout shirts
  • 2 tank tops
  • 2 pairs of jeans (different colors preferably)
  • 1 pair of sweatpants
  • 2 pairs of shorts
  • 8 pairs of high-quality ankle socks
  • 2 pairs of workout tights
  • A microfiber camping towel
  • A bathing suit
  • Merrell Vapor Glove shoes (for working out and hiking)
  • Chuck Taylors or Vans (walking and they match everything)

Toiletries and skincare items

Gear

Miscellaneous

  • Ziplock bags
  • Zip ties
  • Paper notebook
  • Whey protein
  • Vacuum-insulated water bottle

If I forget anything or come across a situation where I lack the necessary clothes or items, I just buy it.

A lot of insurance (think rental car insurance, for example) preys on us worry wart’s insecurities and hand-wringing thoughts of what if my pants spontaneously catch on fire and I lose my wallet? For short trips, it’s a bit of a gamble. For long-term travel, your safety abroad shouldn’t be viewed like an optional nose job. Hopefully you won’t ever have to use it for medical emergencies, but you’ll be glad that you had the foresight to get insurance before shit really hit the fan. Here’s what you need to know.

First, realize that travel insurance is not quite the same as medical insurance. General travel insurance protects the logistical aspects of your trip--flights, hotels, lost luggage, and so on--in case something comes up. Medical insurance protects...well, you.

Before you leave, you absolutely should check with your primary medical insurance provider to see the extent of your coverage worldwide. Some providers will cover doctors in other countries as long as they are in-network, and if not, ask about what they can cover and if you need supplemental policies. If you don’t have a primary health insurance for whatever reason, you can check BootsnAll for a detailed breakdown of different insurance options at different price points.  

Some travel insurance do include medical coverage, too, but the two can also be unbundled. So figure out the exact coverage you want. If you don’t need medical insurance and you mainly want to protect your costly investments in flights, accommodations, or lost, stolen, or damaged property, then you need a trip cancellation policy. If you want some sort of medical coverage, choose emergency-only or get a more comprehensive plan that can cover a high medical bill.

Many companies can cover up to $100,000 in medical bills, which is generally a good amount. Frankly, I wouldn’t go anything less with $100,000. Your health is worth it. Not only do you want a high ceiling for medical costs, but ideally, you would want your insurance to cover emergency evacuation. Let’s say, for example, you’re on a boat somewhere. You’re having a good time, but suddenly you grimly suspect that the all-you-can-eat lobster tails might’ve been funky. Or maybe it was the five frozen margaritas in a row.

Whatever the case, you fall very, very ill and need to go to the emergency room. A good insurance will cover a helicopter to fly out to your boat, wherever you are, and whisk you to the nearest hospital. A popular insurance option that a lot of nomads and travelers gravitate toward is World Nomads. Insurance provides a good cushion for that “just in case” mentality, but mostly, it’ll save your ass from ponying up an exorbitant amount of out-of-pocket fees.

When you inquire about your insurance, make sure to ask what is not covered. And if anything happens, be sure to keep all documentation. You only need to experience this once and deeply regret not getting insurance to always get insurance.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

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Day-to-Day Success

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.

The rest of this content is available for free in the full PDF guide.

Throughout my solo adventures, I’ve been fortunate to break up the solitude with myriad instances dedicated to sharing meals and drinks, arguing about the correct pronunciation of GIF, going on hikes, and generally connecting with other human beings without any sort of ulterior motive. 

About 90% of these were chance encounters that I merely capitalized on. That means, I purposely put myself in situations that allow me to easily meet people and then actually started chatting with people, as long as I can get over that nagging fear of coming off like a dope. One of the easiest places for this was a hostel. Hostel occupants are fellow travelers who are also like a fish out of water in a strange country and are easy to bond with over mutual travel convenience and bizarre observations of the local customs.

When I travel, I don’t spend much time at hostels because of issues with privacy and general lack of quiet work spaces. Rather, I spend most of my time meeting people, in particular locals, through Airbnb. If you truly want the fully immersive experience, meeting and living like a local is the way to go. 

Sometimes my friendly terms with the Airbnb host lead me to meeting their friends and other locals. When I stay long term in a city, I’d check Facebook groups to meet up with a varied assemblage of locals, transplants, and fellow travelers. Maybe it’s a Facebook group for running or ultimate Frisbee; just search for groups based on your interests. In my experience, most major cities have plenty of active Facebook groups for anything you desire. It’s a great way to keep abreast of events and attend to meet people.

Along a similar vein, technology lets you connect to people with common interests from anywhere in the world. I’m talking about apps like Meetup.com and Tinder. I can’t tell you the best hacks for them since I didn’t use them. I do, however, like NomadList as a way to connect with other digital nomads and remote workers. All in all, meeting people is a lot of work.

Make no mistake, meeting people is 100% being comfortable with and proactive about talking to strangers, albeit very rewarding. For more, I’ve written a whole guide on meeting people as a solo traveler and tips for talking to strangers here.

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.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

The rest of this content is available for free in the full PDF guide.

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