How to Get Started as a Digital Nomad

How to Get Started as a Digital Nomad

One of the greatest perks of being a freelancer or working remotely is that you can literally work anywhere. That said, many of us stick close to home but secretly dream about coding, writing,  designing, or doing whatever it is you do from an exotic location.

This lifestyle, known as a digital nomad, is easier than you think to start. It’s not possible for everyone because of family or other lifestyle commitments, but you might be surprised to learn how easy it is to live the nomad life even it’s just for a short period of time.

And, by using time tracking software like Hubstaff, you can rest assured that you will be able to track your hours worked and collect a paycheck no matter where you are in the world.

Test Drive Nomad Life

If you’ve never lived as a digital nomad before, how do you know that you are going to like it? That sounds like a silly question, but the lifestyle is not for everyone and is not always as glamorous as it might seem.

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To gauge whether it will be a good fit for you, consider a trial run for a few weeks. Pick a city or country that you’ve always wanted to visit, make travel arrangements, and find housing through sites like Airbnb, Nomad List, or Couch Surfing.

Here are a few things to consider as you are planning your digital nomad trial run:

  • Is there anyone or anything at your home that needs to be looked after while you’re away? This can be pets, plants, or anything else that needs a little TLC from time to time. These arrangements will need to be made before you leave.
  • Who are your emergency contacts? It’s good to have at least one person in place in case something happens while you are away.
  • Who needs to know where you are going? This includes friends, family members, and your clients and/or coworkers. Consider who needs to know that you will be living and working in a new space. This is especially important if you will be heading to a place that’s in a different time zone from where you currently live.
  • Does your new temporary home have somewhere to work? If not, you’ll need to consider a coworking space or other options with a reliable Internet connection.

Once you’ve picked a place and figured out the logistics, it’s time to figure out what you’re going to be doing during the time that you’re not working. One great thing about digital nomad life is that you have the opportunity to see new things and meet new people everywhere you go.

As more and more people adopt the nomad lifestyle, there are more and more opportunities to meet fellow travelers around the world. Check out opportunities on Meetup, Nomad List, and Couch Surfing before you arrive, and look out for events posted around town once you arrive.

At the end of your trial run, it’s time to have an honest conversation with yourself about how things went and whether the lifestyle is something you can sustain long term. Wait to make this assessment until things settle a little bit after you return home — you don’t want your post-trip excitement or the relief of being home to cloud your judgment one way or the other.

When the time is right, you might even consider making a pros and cons list to help gauge the good and bad of digital nomad life. You should also project how a long-term move would affect your finances and what you need to do to make yourself a full-time nomad.

Adding It Up

Another important factor to consider in deciding whether digital nomad life is right for you is whether you can sustain the lifestyle financially. Before you go anywhere, you should have a steady income that you can sustain for at least a few months while you get on your feet.

If you’re not there, focus your time and energy on building your client base or seeking remote employment that will be easily portable. The motivation to become a digital nomad may be just what you need to move quickly toward securing stable income.

You should also try to downsize and sell as much of your stuff as possible. Consider what you will need to live in your new place or places and get rid of everything that you will not need. This can include your car, furniture, extra clothes, and even things like gym memberships or subscriptions that are based on your home location.

Here are a few other factors to consider as you get your finances in order to leave home:


While not nearly as glamorous as location or lifestyle, taxes are an important factor in deciding where you’ll be based. Each country has its own rules and regulations when it comes to how long you need to live there before you have to start paying taxes.

You can also set up your own business that’s based in the U.S. if you do not want to deal with foreign taxes. This is more complicated and not possible if you work full-time remotely for another company.

Either way, you should consult an accountant and a tax attorney before you begin your journey. Check out Nomad Capitalist for more information about how to plan for taxes as a digital nomad.


Because you’ll be living away from family and friends, it’s important to have insurance in case something happens while you’re away. This includes both health insurance and insurance for all of your belongings.

If you are going to make a living working remotely, chances are you have a pretty nice computer, cell phone, and maybe some other equipment to go with them. You would literally lose your ability to work if that equipment is stolen, so it’s important to have insurance so you can get it back quickly without incurring extra expenses. World Nomads offers travel insurance specifically for digital nomads and is run by people who are nomads themselves.

Depending on your policy, travel insurance may cover some health care costs, but it should not be your sole means of health insurance while you are living away from home. You can choose to keep your existing coverage and pay out-of-network fees, or you can forfeit your home insurance and purchase international health insurance.

The right answer depends on how the coverage you have at home compares to what you can get in your new location, and how healthy you are. Of course, if you are moving from one place to another in the U.S., you can keep your existing health insurance without issue.


Before you choose a place to move to, do your homework on exactly how much it will cost to live there. This includes basics like rent and utilities, but also things like public transportation, groceries, and other items you’ll need for daily life. Nomad List and Numbeo have cost of living calculators for cities around the world.

In all the excitement of moving to a new place, it can be easy to forget about expenses you might still have to pay back home:

  • If you own a home, you’ll need to sell it, rent it out, or pay the mortgage while you are not living there.
  • You’ll still need to make payments on student loans, credit cards, or any other debts that you have. Consider paying down your debt as much as possible before you leave home so you have less overhead to sustain while you are on the road.
  • As we mentioned earlier, you will be responsible for making payments on anything that you don’t get rid of before you move.

Remember that you want to be able to enjoy the places you choose for your digital nomad lifestyle, so don’t cut your budget so close that you can’t afford to have a little fun. Embrace the idea of minimalism to make your money stretch even further and get the most out of the places you are traveling to.

Digital Nomad Misconceptions

Finally, remember that being a digital nomad is not always what it’s cracked up to be. Moving from place to place is not a way to escape your problems or run away from trouble at home. Sure, that might happen for a little while but your life will catch up with you in the end.

Moving from place to place also means that it’s more difficult to maintain relationships with others. In other words, you will be spending a lot more time alone. If you are an introvert, this might sound like a dream come true, but it might be a more difficult transition if you are an extrovert.

And, there are going to be times when you might get a little homesick. Maybe it will come when you are stressed out about a deadline or when things aren’t turning out how you expected. Hopefully, these situations will be few and far between, but you should anticipate them so you can be prepared when the feelings arise.

Like anything, fully becoming a digital nomad will take time and patience through the transition phase. Lean on your support network at home and abroad to help you through any tough times that arise. And, you can always go home if things don’t work out and make another move later when the time is right.

Finally, you might hear that the digital nomad way of life is not safe. Any of the tens of thousands of people out there who live as nomads would tell you that’s not the case. No matter where you are in the world, don’t put yourself in any situation that makes you feel unsafe or uncomfortable.

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Take the Plunge

Once you’ve done your trial run and considered whether the digital nomad lifestyle is right for you, the only thing left to do is start traveling. Even though we’ve spent a lot of time in this post talking about how important it is to make plans (and it totally is), the reality is that you are never going to be able to plan for every hiccup that will occur once you leave home.

Overcoming those unexpected obstacles is part of the fun of being a nomad in the first place. If you can handle a crisis when you are on your own away from home, you can handle just about anything else that life throws your way.

It might be tempting to have someone else take care of all the details for you, and those services are certainly out there, but in the end, you are going to be most committed to a plan that you create and implement. Putting in the effort yourself will give you a greater sense of accomplishment and make enjoying your new lifestyle that much sweeter.

The world is waiting — literally. There are so many great people and places out there just waiting to be explored. You’ve already taken one step toward freedom by unchaining yourself from a traditional office environment. Maybe now is the right time to take the next step and commit to the digital nomad lifestyle.

Are you a digital nomad? What advice do you have for people who are looking to adopt that lifestyle? Share your experiences in the comments.

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