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Digital Nomad Lifestyle: Step-by-Step Plan to Success

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Digital Nomad Lifestyle: Step-by-Step Plan to Success
Many jobs can be done remotely with a quiet place and a good internet connection. If you don't have to be in a specific location for work, why be stuck in one place when you could be traveling the world? This is the mindset of the digital nomad
Jessica Suess
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Jessica is an Australian abroad who has traveled much of the world and is currently exploring South America from her base in Salvador, Brazil. She has a Masters in History from the University of Oxford and is fascinated by meeting new people and unearthing the secrets that underpin different cultures. She is determined to eat, dance, and surf her way across the globe and share those experiences as a travel blogger and freelance writer.

Read more about this author

A lot of times, your job dictates where you live and how you spend your time. This usually means living in a relatively expensive city, dealing with peak hour transits, and sometimes, only traveling during 2 weeks of annual leave! But does it have to be that way?

If you don't physically need to be in a specific location for work, then you can work from anywhere. This is the question that digital nomads have been asking since they first exploded onto the scene in the 2000s.

Digital nomads believe there's more to life than work, so they don't wait till their golden years to see the world. They pursue jobs requiring skills, a laptop, and an internet connection. Then, they make the world their office!

Are you interested in the digital nomad lifestyle? I'll tell you everything you need to know.

What is a Digital Nomad?

A digital nomad is anyone in a field that allows for remote work. They're called nomads because they're always on the move rather than settling down in a specific place.

They're often digital professionals such as programmers, designers, and social media managers. 

Still, digital nomads can do anything that doesn't require one to be in a physical location, like writing and being online therapists.

Many people fall into this post-pandemic category, and now managers and HR specialists can also work remotely.

Rather than just "working from home" to save money on commuter costs and be more available for family members, digital nomads take the opportunity to explore the world. 

The digital nomad lifestyle can look very different depending on the person. For example:

  • Someone who plans to travel and work for 1-2 years before settling down will want to see as much of the world as possible. They might change locations as often as every 2 weeks.
  • Someone who's a permanent digital nomad who doesn't intend to stop traveling will most often spend longer in different locations to get to know them better. 

Sometimes, they'll stay for the full 90 days most tourist visas offer. This group primarily targets new digital nomad visas, which allow a person to live and work in a country for 1-2 years. For example, an experienced professional living in a colder climate might spend 3 months a year working remotely from somewhere near the tropics.

These are common examples, but there's a lot of variation between them. The principle is that you don't let where your job is located dictate where you physically spend your time. If you're new to this scene, there are tons of resources, like digital nomads podcasts, to get you started.

Benefits of the Digital Nomad Lifestyle

Asides from the freedom, there are many other good parts of being a digital nomad.

Life Experiences

You can build your life experience through travel and encountering new people and cultures. I've realized that travel adventures broaden your mindset. Research suggests that travel rewires the brain to make you more adaptable and a better learner.

A Solo Traveler Speaking To A Local Person In South Africa
Image Courtesy of Adventure Travel News

Self Growth

You become more confident and get to figure out what you want. Traveling, especially alone, teaches you to rely on yourself and to become resourceful. 

It lets you experience more, see how others live, and better understand what is important to you. It also shows you what you're capable of, which can be an important confidence builder.


Creativity comes from being an expert in something while using new stimuli to fuel your innovative juices. Working while traveling is the perfect formula for this kind of creativity. Once you're more inventive, you'll be better at your job.

Affordable Standard of Living

You can take advantage of the cheaper cost of living in some parts of the world. Why pay New York rent or European food prices when you could live in a country boasting low rent and affordable, delicious, and nutritious street food? It's really a no-brainer.

A Woman Working On Her Laptop During Sunset
Image Courtesy of IAS Toppers

The Drawbacks of the Digital Nomad Lifestyle 

Living as a digital nomad isn't always rosy, some days more than others. I'll be highlighting some pain points regarding the lifestyle here.


While most digital nomads report being very happy with their lifestyle choice and having no intention of changing them, loneliness is the biggest challenge experienced by most in this field. 

Being far from family and friends can be challenging. It can equally be hard to form meaningful friendships when on the move or when language and cultural barriers are a potential issue.

Learning Curve

As with most things, there's a learning curve to overcome. The digital nomad lifestyle is something that needs to be learned. It can be challenging to balance your time between the things you want to experience and the work you need to do. 

There's the fact that every time you move, you need to find a new routine and develop new productive spaces. This can drain your mental resources, especially when you're just starting.

Administrative Bits

Life admin can become challenging! Maintaining a permanent address, getting important mail, filing taxes, filing for visas, and keeping health insurance can all be massive headaches that add to your life admin challenges.

You May be Misunderstood

Some people assume you're always on holiday or less productive than co-workers in the office. While these preconceptions are slowly changing, being a digital nomad could harm your prospects in some environments.

Unexpected Circumstances

Disasters happen. You may have booked an Airbnb that promises Wi-Fi, only to discover that there's almost no internet connection where you're staying. Flights could get delayed, and you might be in mid-air without Wi-Fi for important meetings or deadlines. 

These are all adaptation challenges for digital nomads. Top tip! Only commit to an Airbnb for 3 months once you have seen the place and tested the Wi-Fi.

Still, while everyone has to weigh the pros and cons of the digital nomad lifestyle individually, a recent MBO Partners survey said most digital nomads are very happy. In 2022, about 69% were set to continue with the digital nomad lifestyle for at least the next 2-3 years.

A Woman Working On Her Laptop outside
Image Courtesy of Finnair

Jobs for Digital Nomads

If you don't already have a career that allows you to work remotely, you'll need to find a new one that makes that happen. Below is a list of the most common jobs for new digital nomads who are breaking into fully remote work:

  • Freelance writer
  • Blogger/Vlogger 
  • Programmer or Web Developer
  • UI/UX or Graphic Designer
  • Social Media Manager
  • E-Commerce
  • Online Language Teacher/Translator
  • Virtual Assistant 

While these are typical jobs among digital nomads, you can do anything location-independent. Several sites like Freelancer and Upwork provide opportunities like that.

How to Become a Digital Nomad Checklist

If you've decided that the nomad lifestyle is for you, then a step-by-step process to getting started is what you need.

Step 1: Prepare Yourself Professionally

To work as a digital nomad, you need a profession compatible with remote working and an employer that supports that lifstyle. This could be with a specific company, or you may choose to freelance.

Ideally, it would be best if you had been on the job for a while or developed a client portfolio.

Suppose you feel there's room for improvement. In that case, you can undertake skills development or start working your digital nomad job on the side of your corporate job before making the transition.

Step 2: Find a Digital Nomad Community

If you're new to being a digital nomad, joining a digital nomad community is an excellent way to get settled into the lifestyle. 

It's an easy way to connect with other nomads, get advice and guidance for specific locations, grow your business, and ease the ache of loneliness. 

There are quite a number of these communities. You can join forums like Nomad List and Reddit subs for digital nomads or be part of co-living and coworking spaces like SelinaOutsite, and Wework

On the other hand, consider remote working programs, such as Remote Year and Go Overseas. Any of these is a great way to connect with like-minded fellows.

Step 3: Decide Your Travel Approach

Nail where you're going to travel, for how long, and what kind of experiences you want to have. Do you want to commit to a fixed travel period before taking on other commitments, or are you open-ended?

Pick your top destinations and do your research. Where are you excited to visit, and what cities in the area will make an excellent base for you as a digital nomad? 

Look at things like affordable accommodation, good internet connectivity, and the availability of coworking spaces.

Ask yourself questions. How long do you want to spend in different destinations? Will you move around by plane or train? What kind of accommodation will you stay in? Are you a hostel, coffee shop gal, or an Airbnb type where you can call your own?

Check what kind of visas you'll need for different locations and how long you can legally stay.

Step 4: Be Prepared Mentally

The digital nomad lifestyle can be a big mental switch. It helps if you learn to release attachment to people, places, and things, learn to travel light, and become a minimalist while on the road.

Think of how you will keep in touch with the people who are important to you and deal with potential issues like loneliness and fear of missing out. 

Watch for how you'll be disciplined and productive when working remotely and how to switch off from work and make the most of where you are when you can.

Girl drinking coffee on a cosy sofa
Image Courtesy of Clayton Webb On Unsplash

Step 5: Get Your Affairs in Order

Assess how you're going to manage your finances while abroad. How will you be paid, where will you pay taxes, and how will you contribute to a social security or retirement fund? If you need to maintain a permanent address in your home country, where will that be, and who can act for you at home when necessary.

Prepare a savings safety net and emergency fund. While there's no correct number for how much that should be, ideally, you should have at least enough to support you for 2 weeks and buy a flight back home if something happens.

This is also the time to start shedding unnecessary commitments. Sell your car, give notice on your lease, or cancel that gym membership. Take out your travel insurance, get a health checkup, and get any vaccines you might need for where you plan to travel.

Step 6: Get Going!

Pack up your laptop and travel bag and head to your first destination. Expect the unexpected and learn to rely on yourself in any situation! Some things you'll only learn by doing.

A Person Packing His Laptop In An Orange Backpack
Image Courtesy of Road Affair

Things to Consider Before Committing to the Digital Nomad Life

Pursuing the digital nomad lifestyle is essential and will depend significantly on your life goals and relationships. But there are also a few things to consider before taking the plunge.

Does Your Employer Support Travel While Working?

While an increasing number of employers support remote working, not all support travel.

Wherever you're working anywhere in the world, your employer is responsible for your health and safety while you're working. Where you work also impacts how much you're eligible to get paid or matters such as your social security contributions.

If you're self-employed or a contract worker, these things are in your hands, and you can decide where you want to be based. If you're an employee, you need to talk with your employer.

Do You Need Visas for Where You Intend to Travel?

Most digital nomads enter new countries on a tourist visa, lasting about 90 days. At this point, they move on to the next destination. If you're from the US or any EU country, you can enter more than 180 countries as a tourist without pre-applying for a visa.

The downside of traveling on a tourist visa is that you will need help opening a bank account, signing legal contracts, using local medical facilities, etc.

Still, insurance companies like Safety Wing provide international health insurance that can cover you while you're on the move. It would be best to look around for the best travel insurance.

Recently, many countries have been offering what's known as digital nomad visas for remote workers that want to spend some time in their country.

The visa requires that you have a stable source of income from a source external to the country you wish to stay in. 

You should also be able to show a minimum income, usually set at about twice the average wage for that country. In return, you get a visa to live in that country, usually for up to a year and often renewable. 

The visa will give you access to a bank account, health services, and other benefits. Still, you won't be allowed to work for companies in that country.

SafetyWing Travel Insurance
Image Courtesy of SafetyWing

Where Will You Be Paying Taxes?

One of the most common questions digital nomads ask is about taxes. And yes, you have to pay taxes wherever you are in the world, and if you aren't careful, you may even have to pay taxes twice! 

For example, you may pay tax on income you earn from sources within the United States in that country. You may also have to pay tax on that same income in the country in which you reside. Ouch!

What most digital nomads do is choose a tax residency, usually in their country of origin, but not always. It's then necessary to maintain a permanent address there, often by using a friend's or family member's address.

Note: Spending no more than 183 days in any country is essential. After 183 days, you become a resident for tax purposes and liable for local taxes.

Plan Your Travel Arrangements

Before you start your journey, be sure your digital nomad packing list is up to date.

One of the secrets to starting a digital nomad journey is remembering that you'll always need more time in any given destination than you imagine. 

Finally, while having a plan is good, the whole point is to say yes to meaningful opportunities when they come knocking. You need some flexibility to take advantage of those.

Start Planning your Digital Nomad Lifestyle with Pilot!

Once you have considered these things, it's time to get into the fun part! If you're planning long-term travel, you'll need a way to keep track of everything, and Pilot is that virtual travel assistant you need.

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Disclosure: Pilot is supported by our community. We may earn a small commission fee with affiliate links on our website. All reviews and recommendations are independent and do not reflect the official view of Pilot.

Jessica Suess Blog
Written by:
Jessica Suess
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Jessica is an Australian abroad who has traveled much of the world and is currently exploring South America from her base in Salvador, Brazil. She has a Masters in History from the University of Oxford and is fascinated by meeting new people and unearthing the secrets that underpin different cultures. She is determined to eat, dance, and surf her way across the globe and share those experiences as a travel blogger and freelance writer.

Read more about this author
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