The Digital Nomad’s Roadmap – A Complete Guide: Successfully Live, Work, and Travel Anywhere
by Anne Dorko
So you wanna be a digital nomad. I’m not surprised: the future is bright for freelancers and location independent workers.
Statistics show 40% of Americans will be contingent workers by 2020. That’s a lot of potential for digital nomads! Yet there’s no hands-on guide on how to transition from office employee to nomadic freedom. Where does the savvy to work while moving about the globe at will come from? Right now it’s scattered across a gazillion blogs in a bunch of tiny pieces.
Digital nomadism is not for the faint of heart. Before starting your journey, become familiar with the ups and downs and the unique challenges, I also recommend to check theguidr.com so you can read some reviews. Learn what you’ll need to handle those situations when they arise. It’s always trial by fire in the end, but there’s no harm in donning a flame retardant suit before jumping in. Safety first.
What you see here is an ultra guide, mega resource, and all-around master post for aspiring digital nomads. One might even call it a roadmap of sorts.
As this is such a long post (you might bookmark it for later), I’ve broken it up into several clear sections. These are:
Ready to move toward personal freedom, global exploration, and a generally kickass kinda life? Let’s go.
What is a Digital Nomad?
Digital nomads leverage the power of telecommunications to work and travel anywhere around the world.
The term “office” starts being really flexible.
It takes the idea of road warrior to a whole new level and puts the more common telecommute on steroids.
There’s no doubt location independence has captured the imaginations of thousands. Yet it remains an unattainable reality for many people interested in ditching their cubicles. Digital nomadism, though practiced all around the world, is still coming into definition. Those who have gone ahead are still blazing the trail.
“It always seems impossible until it’s done.”
– Nelson Mandela
Things we once thought were impossible, once we see them done, are quite achievable. Almost as if our psychology limits our abilities until something shows us it’s completely possible.
How Do You Imagine Life as a Digital Nomad?
I asked a few people what their vision of “digital nomad” is, and what’s stopping them. Here’s what they said:
“[Being a digital nomad is] living normal life, chatting to the local shopkeeper, going for my morning jog around the neighborhood, doing some work, eating out at my favorite local food joint, enjoying the company of the people around me – just – in a completely different location / country / culture every few months.
My biggest challenge is negotiating a relationship in which our goals don’t completely line up. My partner wants to work on the road also, but he has very different goals. […] This involves a lot of patience, a bit of waiting around, being flexible with plans, but also knowing when it’s time to just do you. I have learned (albeit rather slowly) where the line is and how to defend my own experience while still being open to experiences with my partner if the opportunity presents.”
“I always wanted to see more of the world than my little corner. I understand I will be spending a lot of time working, especially at first. But anytime I am not working I will get to see something new everyday instead of sat watching TV or the usual mundane things that people do after a day at work.
Leaving my safe job in a factory where I have worked for 25 years will be the hardest thing I have ever done. I will be putting it off until after I purchase my first one way ticket. I have a lot of life-long friends I may never see again. At this exactly moment I am finding clearing my house out to sell overwhelming as I have collected so much rubbish over the years. Trying to fit a three bedroom house into a backpack is going to be a bit of a squeeze.”
But what does it really look like, to be a digital nomad in practice?
Each successful digital nomad out there sharing their experiences makes it easier to follow suit. The road is different for each of us, but the core problems we face are so often the same. Knowing it’s possible for the digital nomads already out there makes it possible for us.
If the best way is to see how it’s done, let’s follow the folks who have already paved the way.
Examples of Digital Nomads
The most famous of digital nomads have built entire brands and businesses around their travels. You’ll know these names if this topic has interested you for a long time.
But there’s also the quieter digital nomads out there minding their own business. They’re just as inspiring. In fact, I find them to be even more so. You can still follow their experiences through social media and their personal blogs. So, without further ado, here’s a list of self-proclaimed digital nomads both big and small.
What do they do? Supports themselves with freelance writing and web development. Teaches the art of turning obstacles into opportunity, a.k.a. achieving lifestyle freedom.
What does she do? Travels the world while running her own business. She is passionate about food, adventures, learning new things, meeting new people, health, and figuring out how to do this all in a sustainable way for the long-term.
What does she do? Supports people who are moving, living, and working abroad by helping them tackle the challenges and transitions that come with a global lifestyle.
There are so many more out there, but this will get you started.
So there you have it! A curated list of inspirational digital nomads to follow. Now that you can nerd out on these guys, it’s time to see what they have to say about the lifestyle.
Note: Images pulled from social media accounts and public blogs! Please notify us if any need to be removed.
Advice and Inspiration
Every digital nomad comes with their own brand of wild and crazy tales, along with lessons learned.
It’s exciting, I know. You can dig into their adventures on your own time later. I’ve done the hard work of pulling out the meat and potatoes for you. Here are the stories, quotes, and advice coming straight from the digital nomads themselves that I’ve selected to share with you!
Advice For a New Digital Nomad
“Get to know yourself really, really well; don’t get tempted by doing everything or what everyone else is doing.
Know your limits and take care of yourself. Be sustainable in your travel. Here is the compass I created when I first set out—I’ve gotten in trouble every time I deviated too much from this (but this compass comes from years of knowing myself really well).”
– Natasha Murashev
“To live is to learn. I see no other way. The day you stop learning is the day you stop living. Forget about all concepts of success or failure. If you give it your best and learn something, then you’re successful. So it’s impossible to fail. Err on the side of action. Try that new thing, build out your new idea, go somewhere you’ve never been before. Money does not equal wealth. Living each day the you were meant to, the way that you want to, is wealth. Make it happen now; don’t wait. Putting things off until the future will postpone your dreams forever.”
– Danny Flood
“I’m all for getting a mentor who is where you want to be at. Just do exactly what they tell you to do to build up a business. A lot of digital nomads I’ve met are still just freelancers and forget to see how they can step into the owner role of a business and start thinking about leveraging other people to build up their businesses and do the work.
Virtual assistants are the reason I’m able to live the life I’ve led so far and I highly recommend hiring people to free up time.”
– Chris Hughes
“I’m a big fan of old sales, marketing, and self-help stuff. When I was a kid my mom had some Zig Ziglar cassette tapes and on one of them Zig Ziglar said “You can have everything in life you want, if you will just help other people get what they want.”
I was a dumbass, so it took until I was in my mid-20s for what he was saying to sink in. Before then I had been trying the “me first” thing and it had gotten me nowhere. Once I made the switch from trying to force my thing to helping other people do their things, everything started to click.”
– Michael Noland
“My word of advice to anyone wanting the digital nomad lifestyle is to dream big. Be bold, but realistic at the same time. Always follow your dreams, but expect to work really hard to get there. If your focus lies mainly on traveling, then make sure you have enough savings to back you up. Marketing your services takes up a lot of time and energy in the beginning.”
– Gaby Kamp
A Few Digital Nomad Stories
“No matter where I go, I find amazing people (or they find me). Every step of the way, from my first working trip in 1995 to Naknek, Alaska, to my years in Peru to my recent time in rural Southern Missouri caring for my aging dad, when I need cool people in my life they appear. Without fail.
Part of this is because I do research and start networking online before I go somewhere, and another is I ‘get amongst’, as my Kiwi buddy Shane says. For example, my first morning in Lima I had arranged to meet for coffee with an expat who rented out this luxury apartment overlooking the ocean. We didn’t hit it off, but a friend of his who joined us that morning has become a great friend of mine, and through him I had a social circle on day one.
After living in Lima for several years, I went out into the jungle for a while to help a local curandero start his traditional healing center. When I made it back to Lima many of my friends had gotten married, moved on, or whatever, and I didn’t have my social circle anymore. So I decided to build my own.
I started up the English Club of Lima, a social club for people to practice conversational English in Parque Kennedy in Miraflores. An ex-girlfriend introduced me to a beautiful Danish girl who liked the idea and wanted to help. Her magnetic personality attracted people like moths to a flame, and soon I was meeting up to 50 new people each weekend.
I’ve found that if somebody is doing something cool or fun, you can count on there being like-minded people around. Find interesting things other people are doing and offer to help. Better yet, come up with a project of your own and invite others to join in. For me, it’s working like a charm.”
— Michael Noland
“My main reason for becoming a digital nomad is because I got tired of starting over in each country I travelled to. I’ve worked in Nigeria, China, Argentina, and now Belfast, and each time I had to find a new job or project and start over. I wanted to build up a steady career which would allow me to be location independent so I can work, make money, and continue with my reason for traveling (which is immersing myself and learning about cultures, preferably non-western cultures).
I also created my business because I saw a need among the expats and digital nomads in the various countries I visited. I have a background in counseling & training and I got to talking with quite a few Global Nomads who were all eager to have someone to talk to who understands their lifestyle. With Global Nomad Coaching I have created a platform where Nomads can voice their life experiences and struggles, share with others, and, for those who are not sure where to next, find a way to move ahead. The Nomads I’ve met want to know if they are the only ones struggling with various issues and figuring out how to deal with the many life transitions that come with their nomadic lifestyle.”
– Gaby Kamp
Challenges and Difficulties
Digital nomadism comes with unordinary challenges. This is especially so when you take the freelance route. Choosing total self reliance also means running a small business.
It is a journey filled with introspection while you battle your deepest fears on a daily basis. A side serving of self doubt, anyone? All this for the freedom to take independence to a whole new level. Every single day is trial and error.
Not to freak you out, but I’ve compiled a short list that touches on the common challenges faced within the digital nomad community:
Internet access
Cash flow (or lack thereof)
Currency conversions, ATM, and banking fees
International insurance
Productivity and time management
How to handle a home address without one
Romance and dating on the go
Always temporary housing complications
Visa and border control issues
Global cell coverage
Language barriers
A mortgage might start looking good about now. Nah…
I can’t promise to solve all your problems, but I can point you in the right direction. At least you’ll be aware of the common pitfalls before you find yourself in a serious pinch!
Rookie mistake: Trying to fly into London without a minute-by-minute pre-booked itinerary.
Becoming a savvy digital nomad comes in two parts. First, learning to travel smart. Second, learning how to work on the road. If you chose the freelance route, you get a third tier: learning how to run a business.
The following advice will not make you an expert on these matters. Instead it will open your eyes to the typical problems of the digital nomad world. And in a world where you must expect the unexpected, it’s best to learn as much as possible so you’re never caught completely unaware.
Internet Access
A digital nomad needs internet. It is an integral part of the gig.
Your every waking moment can quickly become a scramble for how and when you’ll be getting decent service again. Your work and your clients need you.
A few quick fixes:
The obvious spots are coffee shops, libraries, and public hotspots.
Try coworking and otherwise shared or temporary office spaces.
Real solution:
Time management. Learn to batch your work into the times you have great internet connection, and you can spend days at a time not worrying about the next time a wifi hotspot will show itself.
Cash Flow
Learning to keep a budget is hard work, all on its own.
Ideally you should be able to run off of emergency cash for at least three months in the event that your contract ends or you lose your job. That means you should be throwing your spare change into a savings account whenever possible.
If you run a freelance gig, you’re going to need to take your accounting and marketing outreach more seriously. Tracking your exact income and outcome will help you predict what you’ll be able to afford and how much more cash you’ll need to make (or stop spending) monthly to reach your goals.
Currency Conversions, ATM, and Banking Fees
Every bank is a bit different, and some offer great foreign policies or even ATM refunds (with limits). In the meantime, it’s also a good idea to research the local banks in the country you’re currently staying to discover who charges the least ATM usage fees.
Be sure to look for:
Currency conversion rates and fees levied by cash exchange companies
Foreign banking and reporting it appropriately for taxes in your home country
Cost to withdraw/spend money abroad with your bank or credit card
For example, I use USAA. They refund ATM fees up to $15 USD per month and offer competitive exchange rates.
General Risk Assessment
Life as a digital nomad means a lot of risks. Learning how to assess those risks quickly can end up being the difference between life and death… or at the very least, a good deal or getting ripped off.
To be fair, many of your risk assessments are more geared towards things like choosing the right insurance levels. Others will be how to time the purchase of plane tickets, pick out a reliable AirBnB apartment, or find a safe CouchSurfing host. From there, you’re in the markets making sure your pockets don’t get picked, learning when and where your laptop is safely stored, and mostly just hoping for the best around every corner.
It’s best to keep your eyes open and intentionally learn the lessons they teach along the way.
Insurance
Getting insurance can be a royal pain.
It took me more than 2 months to successfully communicate my insurance needs, choose a plan, and get the paperwork completed when I first began my journey to a more permanent visa in Germany.
There’s a few steps to choosing the right insurance:
Know your own medical needs and start by researching companies that cover any of your pre-existing conditions
Know that comprehensive insurance is expensive
Additionally, you may want to invest in some travel insurance, and/or rental insurance that covers switching international locations. Not everyone travels by hotel every day of the week (that’s expensive and exhausting), so there’s a good chance you’ll find yourself in a semi-permanent residence for a few months at a time.
Also worth researching:
Travel insurance
Rental insurance when you have a more long-term apartment
Handling Productivity
Productivity is a problem in most people’s lives, but whether we learn to successfully manage it becomes a critical survival point for a digital nomad. Without being able to prioritize our time, we lose out both on valuable work and amazing life experiences, both of which make us feel guilty about the other.
Ugh, and you thought you had troubles with your service at home. Traveling only makes this even more complicated.
Depending on how long you plan to be in any given area, you have two options:
Get an international plan from your home country (I use T-Mobile’s Simple Choice plan)
Buy a local SIM from each country as you go
My best advice is to get a data plan with some basic texting included. Grab yourself a Google Voice number, route all your messages there, and make your phone calls over data. That way you don’t have to memorize every new number you get your hands on.
Visa and Border Control Issues
Having an abnormal stream of income, low bank accounts, or traveling “without a plan” can become problematic as soon as anyone begins asking questions.
Always travel with the right visa permits
Try to have over $2,000 in your bank account at a minimum
Know in advance how strict the country is on having booked hotels, hostels, and/or a ticket out of the country
There’s always an element of risk, and at the end of the day you’re at the mercy of the agent at border patrol.
In general, it’s good practice to have these on hand when you get to the border:
Name and address of where you’ll be staying when you arrive
About how many days/weeks/months you will be staying
The date and flight number of your exit flight (or train information, etc)
Know the airport (Port of Exit) you flew from
Keep your ticket stub, you usually need the flight number
Your emergency contact information
A screenshot of your bank account balance from the last 24 hours (live access is fine, but wifi/service isn’t always available)
If you don’t do it right, you could wind up like me and get interrogated for four hours in the middle of the night without real cause… all because the lady didn’t like that you weren’t on top of everything.
Complex Housing Situations
Apartment shopping can be hard to begin with, but matters get worse when you’re always looking at short term.
Many times you’ll need to think outside the box. Here’s a list of the usual suspects:
Short term rentals (using the local listings or sites like AirBnb)
Long stay hotels
Shared hostel rooms
CouchSurfing (don’t assume more than a three to four day stay per couch)
WorkAway for two to four week stays or more (check local government regulations)
Love, Romance, and Dating
Dating as a digital nomad is incredibly complicated. You’re never sure how long you’ll be in one place or who you’ll meet along the way.
If you thought love and romance was hard already… buckle up. It’s a whole new level when you’re a digital nomad. You’ll need to really know what you want from life, or you’ll quickly find yourself compromising for others.
You can try to warn your potential mates with this article about dating a freelancer.
Language Barriers
Speaking of interpersonal complications, always dealing in foreign languages takes any daily activity and makes it 1000x harder.
Snail mail is unfortunately still a reality we must deal with.
If you’re lucky, you have family members who are willing to take on this task for you. If not, you’ll want to look into mail services that can sort, scan, and forward your mail as appropriate.
This is still a relatively new service that local government has not yet caught up with. You should make sure to note any local laws that would make updating or changing your address to use one of these services will not cause issues for you down the road.
The legal world is simply not structured for digital nomads and while we’re not usually going against the spirit of the law, it can become problematic when it comes time to really define what’s going on. Whether it’s having a local mailing address or knowing which is the right visa to apply for, all the fine print can make for a confusing situation.
You simply do your best to stay above board, keep to the local laws and get the appropriate visa.
Basic Requirements
There are three basic requirements that you’ll need to successfully become a digital nomad.
1. Basic Computer Skills
The first part of the term is “digital,” which indicates at least a basic knowledge of computers. In some cases, you really do just need a basic knowledge.
To jumpstart your knowledge, here’s a flowchart:
2. Critical Thinking Skills
In general, you’ll be expected to handle your digital life and work with grace and timeliness. Otherwise you’ll find yourself without pay or a means to support yourself.
You need to be clever about the way you manage (and charge for) your time, as well as finding out what works best for you to make you happy. In the end, this is all about freedom.
Sometimes you’ll find yourself in a situation where things didn’t pan out quite like you wanted.
There are extremes. Like getting yourself stuck in a Norwegian bus-station overnight in winter or homeless in Liverpool on a Friday night while you watch the local drunks throw burgers around a fast food restaurant.
More likely you’re stuck in an airport overnight after a missed flight or the couch you’re surfing on isn’t quite as comfortable as you expected. There’s any number of niceties you’ll have to forgo on your journey. That doesn’t even get into the possessions you may need to leave behind in the first place!
I talk a lot more about this over at Leaving Work Behind, and what it takes to really live the dream.
How to Become a Digital Nomad
If you’re not hugging your cubicle wall at this point, sobbing for forgiveness that you ever planned to leave… Congratulations! You just might be cut out for the digital nomad lifestyle.
Now that you’re prepped for reality, it’s time to crack down on actually making it happen.
Step 1: Make a Dream Plan
You’re probably already imagining what your life as a digital nomad looks like.
Brainstorm like crazy here. Nothing is off limits. You want money flowing into your bank account daily with your feet kicked up in front of the ocean? Done. Thinking about jetting away to a far off land on a whim? No problem.
Go big. Write it all down.
After awhile, take pause. Try to find the underlying motivations behind your passionate scribbles. Is this about seeing new places? The novelty of travel? Impressing people? Learning cultures and languages?
Look inward and try to understand what it is you want. Think about who you are and what you enjoy on a daily basis.
Tropical islands sound great on paper, but do you even know why that’s what you want? What if it turns out you hate heat and humidity so much that you can’t stand it?
If you don’t know what’s important to you, you cannot know how to adjust your game plan down the line.
How I Did It
When I started working towards becoming a digital nomad, I had no idea the term even existed.
My real origin story began back when I first quit my job and took a crazy road-trip, but that was more akin to Peter Parker in that I was bit hard by the travel bug. All I knew, was I couldn’t settle for normal.
Things really kicked off as I plotted out a one year trip around the world, in which I would study a variety of skills in different places. At the time, I had no realistic idea of how to make something like this happen. But it was my dream goal.
Step 2: Break Your Dream Into Realistic Pieces
Let’s say you want the financial freedom that $100,000 per year gives you. It’s time to whip out the calculator to see how much you need to earn before taxes. These numbers will all sound insane and out of reach. Keep with it.
Now comes the fun part. Devise a plan to reach that number. Hatch a plot. Make a scheme. Go wild!
You’re here for the freedom. Using your imagination to create a better future is crucial for success. Let your mind go wild with the power. Think of every single possibility.
Okay. Was that fun? (Don’t lie, I know it was.)
Now you’re warmed up. It’s time to get down to business. Take all those wild schemes and generate at least a few semi-viable ideas. Got some?
Pick your favorite.
Okay, take that plan and break it into its most basic steps. It’s easiest to break things down on paper. Start by writing the ultimate goal on the top, like $100k annual income.
Write your scheme beneath that. What are the basic requirements to make that realistic?
Write them down next on the list.
Of those requirements, which are you most capable of acquiring first?
Circle it.
What steps would you need to take to get it?
Jot down everything that you need. Write it all down. You’re almost ready to start rocking it out.
How I Did It
I knew to get where I wanted to go, I needed a direction to start in. Even though I had taken on a decent job teaching at my alumni college, staying in my hometown made me feel stuck in a rut.
When my dream was to move around, see the world, and experience new things—staying in place felt counter-intuitive.
I started looking for other places to live, to move me out of my comfort zone.
I began making new connections and friends, even working weird jobs to build new experiences and save up cash.
This led me to moving to Austin, TX and starting everything fresh.
Step 3: Take The Next Step! Do That Again… And Again… And
By this point you should be looking at a lot of action points.
You can order them in a few ways, which all depend on your current situation.
Chronological plus urgency. If your action points need to go in a certain order because of reasons, start here.
Affordability. Sometimes your action points involve expensive things, and you might not have the cash. Start small. While you’re at it, use that imagination again and get creative to work around these cash problems.
Easy wins. There’s nothing more motivating than feeling like you’ve already started making progress! Get some momentum going by knocking out items that make it easiest to feel accomplished.
There should be some clear next steps you can take. Find one you can do right now. Do it.
Did it feel good? Awesome. Do another one.
Okay, now keep doing that.
How I Did It
Everything was a day-by-day procedure. I was also dealing with a huge bout of depression, so this literally meant focusing on my basic needs (like eating) some days. Other days, it meant actively chasing my round-the-world dreams.
Whenever I had the motivation, I took huge strides.
If I was having an off period, I let myself retreat and recharge.
I always kept in mind the ultimate goal: being able to up and relocate at the drop of a hat.
I was constantly pushing myself out of my shell by going out to bars, social and networking events, working those weird jobs, and eventually meeting some interesting people with similar goals. Meanwhile, I regularly reduced the number of belongings I had so I would be ready for travel one day.
Step 4: Take (Calculated) Risks
From here on out, it’s a matter of adjusting that compass and knowing when it’s worth forging onward—and when it’s time to fall back.
Always remember what your ultimate goal is. You’re the only one who can judge whether those risks are worth it.
How I Did It
Knowing what I really wanted kept me focused. It helped me know when a sacrifice was worth it.
When someone I met through these connections offered me the opportunity to travel the world, I knew it was in line with my dream and worth dropping everything else for.
All I had left to do was say “Yes!” and pack my bags. The journey was never easy (even after taking off); there’s always a price for these things. But, the adventure never could have happened if I hadn’t taken all the steps that led me up to that point.
Since then, I’ve traveled around the globe, found the courage to do a solo bicycle tour, and even moved to Germany to embrace a new culture and start learning a new language. My original vision of “one year around the world” has changed, but the motivations behind it are still the same, and I’m actively making it happen with each new step.
Ways to Become a Digital Nomad
There’s no one correct way to be a digital nomad. The point is to have autonomy and freedom to be where you want, when you want.
Here are some of the things you can do to get there:
Learn the Right Skills
Digital nomads all have one thing in common: they use the power of digital tools to make a living. Here are a few topics that come in handy when you open your door up to the entire world.
Event planning
How to run a business
Marketing
Basic sales
Computer basics
Social media
Designing a website
Writing a blog post
Taking and editing photos
Put Your Skills to Work
So with all those types of skills, what can you do?
