5 Ways to Prepare for a Seamless Transition to the Digital Nomad Lifestyle

This is a guest post from our friends Kristen and Gaby. They built two successful online businesses and now travel the world full-time. These are their tips for transitioning into the digital nomad lifestyle. This is really stellar advice!

As a new digital nomad, there’s a lot that can go wrong.

Not to get all doomsday on you, but when you go from working a regular (aka comfortable) 9-5 job back home, to working online and traveling full time, there’s a ton of room for error.

Not only do you have to figure out how to make a steady income all on your own, but you also have to learn how to smoothly navigate new, foreign countries on a regular basis.

And while that might sound like the ultimate dream from the outside, once you’re in the thick of things, it means endlessly researching visas, establishing a life in places where you don’t know the language or customs, and packing up everything you own each time you head somewhere new.

Now look, you and I both know being a digital nomad means living a lifestyle most people only dream of. And after all the planning and navigating involved, there’s nothing in the world that tops it.

But if you’re not prepared for what’s to come when you transition to life on the road, you could find yourself struggling through what should otherwise be amazing experiences.

Keep reading to learn 5 ways to transition into the digital nomad life and avoid months of trial and error, frustration, and mishaps.

Know the Visa Rules

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Visas are confusing because the rules depend on:

  • Which country you’re going to
  • What you’ll be doing there
  • How long you’re staying
  • Which country you’re from
  • And more

In other words?

There’s no hard and fast rule when it comes to visas. If you don’t have the proper visa to enter a country, you could find yourself turned away at the border. (This gets harder if you’re traveling with someone from a country different than your own as their rules are different.)

Before you ever book a plane ticket or Airbnb, always research visa requirements.

A great place to start is by using a site like Project Visa where you can choose which country you’re visiting for a list of general visa requirements.

Keep in mind, some countries have agreements with other countries, where visa and visitor rules apply across the board.

Take the Schengen Zone in Europe, for example, where you can travel between select countries without going through immigration, making your travels incredibly easy. The caveat is, most tourists are only allowed to stay for 90 days total (out of every 180 days) within the entire zone.

That means if you stayed in France for 90 days, then wanted to travel to Italy (both countries are within the Schengen Zone), you’d have to leave the Schengen Zone for at least 90 days before you could enter Italy.

Another confusing one?

When entering Thailand by a land border crossing (by bus, for example), you’re only allowed a couple of weeks within the country if you haven’t applied for a longer stay visa ahead of time. If you’re entering by plane, though, you get 30 days.

There are different rules and quirks like this all around the world, so always do your research before traveling somewhere new.

Have a Money Plan

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Accessing, spending, and making money while abroad will always be different compared to when you’re home.

Normally, when you need money, all you need to do is head to the bank and withdraw it.

And your payments? They’re likely sent straight from your employer to your bank account. And if not, depositing a check at your bank (or through your bank’s app) is simple.

Likewise, when you head to the store to buy something, there’s not really much to think about, is there?

When you’re traveling, though, all those things change.

If you need cash from an ATM you first have to decide whether all the fees are worth it. And, if you’re exchanging currencies rather than withdrawing, you need to consider how much money you’ll lose from the commission taken out.

On top of that, when it comes to getting paid, things can get even more complicated. If you’re freelancing, for instance, you might have to use whatever payment form a client chooses. (Side note: If you don’t have a PayPal account, now’s the time.) Alternatively, you might be paid through several different outlets. In those cases, you’ll need to consider what sort of fees you’re accountable for and how it affects your taxes.

Spending money can be just as challenging. What happens when a store clerk asks if you want to pay in USD or the local currency? And how much should you tip, if anything?

If you’re not yet sure how you’ll be handling your money while abroad, now’s the time to figure it out.

At the very least, I suggest looking into a no-fee debit card like the one offered by Charles Schwab Bank. It’s not available to everyone, but it’s worth checking out if you’re from the US. We use a Schwab debit card and have had hundreds of dollars in ATM fees refunded over the years. If you’re not from the US, try Googling “no fee debit card” to see what options you have.

When it comes to getting paid for your work, decide how you’ll be paid and in what currency. Many freelancers use a free Paypal account, but you can also use payment processors like Stripe if you’ll be selling products. If you’re using sites like Upwork or Fiverr, they’ll generally give you different options for being paid.

Knowing how you’ll accept payments ahead of time will make the process smoother, and not only that, it’ll make you look more professional.

Another smart thing to do is lookup tipping norms before you head to a new place. In some cities and countries, tips make up the majority of service workers’ wages. In others, tipping doesn’t happen at all. And that thing I mentioned about paying in USD versus the local currency? Generally, the amount charged in USD is higher than what you’ll pay in the local currency, so always request to pay in the local currency, even if you’re not asked your preference.

Make Health a Priority

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I know far too many digital nomads who throw their health to the wind when they start traveling. When they leave their home countries behind, they simply forget all about scheduling regular doctor or dentist appointments.

Traveling full time isn’t a good reason to stop taking care of yourself, though. In fact, it’s a great reason to start taking better care of yourself. When you’re constantly using public transportation, exposing yourself to new foods and surroundings, and likely getting less exercise and less sleep than you need, you’re far more susceptible to having health issues.

Before you start traveling full-time, look up travel clinics in your area to see what (if any) vaccinations you’ll need. These can generally be purchased for low prices, and if you have health insurance, many are often free. If you can, get a physical, too, just to make sure you’re healthy before hitting the road.

While you’re traveling, make regular health check-ups a routine. In many places around the world, healthcare is affordable, without sacrificing quality. You can have preventative tests and checkups done at world-class hospitals in Thailand, for example, for thousands less than it might cost you back home. Not only that, dentists all over the world are easy to schedule appointments with and will give you excellent treatment without overcharging you.

It can be intimidating to find healthcare in foreign countries where you don’t speak the language, but do your research, and you’ll likely be able to find places along the way to stay ahead of the game when it comes to your health.

Even more importantly, make sure you buy travel medical insurance in case you get sick or injured abroad. While quick doctor and dentist check-ups might be cheap out of pocket, medical emergencies can cost thousands. A good travel insurance policy could save your bank account (and you) if anything happens.

Pack Correctly

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Packing is like an art form for digital nomads — it has to be when you travel full time with your entire life in one or two bags.

To be comfortable while traveling, find a balance between having too much stuff (which is a pain to haul around) and having too little stuff (which means you’ll probably end up buying more every time you land somewhere new).

The best way to pack as a nomad is to:

  1. Find compact gear that’ll turn any kitchen or coffee shop table into a comfortable workspace.
  2. Buy multi-use clothes and gear.

We all know you can’t keep doing the travel thing forever if you’re not making money. So, as a digital nomad, you’ll be working a lot. Having simple things like a laptop stand, external keyboard, mouse, and noise-canceling headphones can make all the difference in the world.

Depending on what type of job you have, it also might make sense to travel with a few odds and ends specific to your work. If you teach English online, for example, you might need completely different gear than someone who works as a developer or writer.

Evaluate your needs, then see how compact you can make your “office” setup.

Not only that, your clothes need to be functional. Scarves that double as headbands or down jackets that pack into tiny balls, for example, are perfect for full-time travel. It might not be what you normally wear or think is fashionable, but I promise you’ll be thanking yourself down the road for packing in a practical way.

Download the Right Apps

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Physical things become less and less important when you’re traveling, while digital things become invaluable.

Put simply, having the right apps before you start traveling can make your transition into the digital nomad lifestyle immensely easier. Having simple ways to automate travel plans, and work can make a drastic difference in your day-to-day life.

A few of our favorite apps are:


TripIt is an app that organizes all your travel information into one, convenient place. Every time you book an Airbnb or buy a plane ticket, simply forward your email itinerary to the app. Once you do, it’ll pull out all the key information and organize your trips in chronological order.

That means all your flights, train tickets, hotels, apartment rentals, and more can all be stored and displayed so they’re easy to find and reference. Not only that, TripIt will pull in your departure gates, directions, and even travel updates if a trip is delayed. It’s like an all-in-one travel planner. There’s no better way to keep your life organized as a full-time traveler.


Your taxes and finances will be different as a digital nomad. Working as a business owner or freelancer means you won’t get a W2 form (for US employees) like you normally do. Instead, you absolutely have to start tracking your income and expenses if you don’t already.

This can be a tedious task, which is why there are so many personal finance apps available. Most of them, however, are too confusing or cost too much for what you’ll need them for.

Wave is the perfect option for tracking both your personal and business finances without having to shell out a ridiculous monthly or annual fee. With this software, you simply connect your relevant accounts, and the app will automatically help you categorize your income and expenses, making taxes and financial management easier to handle.

Express VPN

When you travel full time, it often means connecting to sketchy, public wifi. This makes it easier for hackers to steal your information.

A VPN is a type of software that allows you to mask your private information, even on public wifi. That means, if you connect to the internet at Starbucks and need to access sensitive information online, you can do so without worrying about anyone else accessing it, too.

Not only that, certain apps and websites (like Hulu or banking apps) aren’t accessible outside the US or your home country. With a VPN, you can connect to a server within whatever country you want, which makes that service think you’re in that country — allowing you to sign into whatever site you need, even if it’s blocked where you are. (If you’re prone to a Hulu binge every now and then, this will be a lifesaver.)

We use Express VPN but there are tons of options out there that work the same way.

Taking the Final Leap

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Will you ever be 100% ready to take the final leap into the digital nomad lifestyle?

Probably not.

The reason?

A lot of it depends on you — on your personal preferences, likes, dislikes, and tendencies.

This guide will help set you up for success early on, but it’s important to expect some obstacles to pop up along the way.

In fact, the best advice on how to prepare for this transition is to be adaptable. Remind yourself to take a breath when something doesn’t go as planned (which will inevitably happen very often).

Being a digital nomad is all about living a life of change and adventure. Each week or month might be completely foreign from the last.

Prepare as much as you can, but then embrace the unexpected.

It’s all part of the journey.

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Kristen and Gaby run two online businesses while traveling the world full-time. After living most of their lives in Texas and New York, they sold all their stuff and hit the road with no end date in mind.

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Making the transition to the digital nomad lifestyle can be overwhelming. These 5 tips will be sure to make it as seamless and easy as possible. #digitalnomadlifestyle #locationindependent #traveltips
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