How to Succeed in the Digital Nomad Lifestyle

Kristin Wilson
7 min readSep 25, 2018
Genuinely happy to (still) be a digital nomad. Selfie by OG digital nomad, Kristin Wilson.

The journey of becoming a digital nomad can range from deceptively simple to overwhelmingly impossible. Cliché stories abound of people who claim to have walked straight out of their cubicle and into the airport, buying a one-way ticket to Bali and never looking back. Or so they say.

Then, there are the Type-A aspiring nomads who fully appreciate the paralyzing complexity of effectively and comprehensively accomplishing the task before them. This, of course, can include everything from changing careers to learning new skills to choosing where to relocate to ensuring you have set up your business and tax structure in the best way possible.

The potential length of your to-do list before even taking the first step is head spinning.

The Truth About Becoming a Digital Nomad

The problem in the case of the corporate corporate employee on his way to Bali is that he’s overly simplified things. Getting burnt out or fed up at work and making a snap decision to fly across the Pacific with a backpack may sound liberating and exciting, but it’s not a sustainable or responsible one.

That one-way ticket can quickly culminate into a two-way street back to square one — if you’re lucky! If not, you could end up like one of the many people who are stranded abroad without enough money to buy a ticket home. It happens more often than you’d think.

On the other hand, a perfectionist planner can end up so bogged down in the details that it could take her years to achieve her dreams, or worse — she might never take the first step.

Neither case is a good place to be.

There are numerous details involved in planning a life change or move abroad. But by focusing on four basic premises, you can increase your chances of long-term success in the location independent lifestyle before you even take the first step.

If you have these things covered or have considered them at all before taking the leap, you’re already ahead of the pack.

How to Succeed as a Digital Nomad

Number 1: Have a Reliable Source of Income

It’s a lot easier to set this up before you hit the road. Slow and steady wins the race. It’s better to simplify your life and cut back on expenses for a while compared to jumping in without a financial safety net.

You can earn revenue in many ways — just pick at least one or two and make sure you can depend on it:

  • Remote salary
  • Freelancing work
  • Passive income from investments or online sales
  • Retirement funds
  • Etc

Fight the urge to “figure it out” when you get there — wherever there is.

Number 2: Stay Open-Minded With a Flexible Attitude

You’re planning to leave the “Standard American Lifestyle” for something completely new. You’ve got your known knowns, your known unknowns and your unknown unknowns. Expect the unexpected, take things with a grain of salt, retain your sense of humor, and that’s a good start.

After polling some of my 1,000 relocation clients from the past 7 years, the most common tips with regard to going with the flow were:

  • 1) Have some form of funding: current work-related income, passive revenue, retirement, inheritance, the sale of a business, or some other type of paycheck.
  • 2) Maintain flexibility: Veteran nomads attribute flexibility in all areas to their success. From designing their own flexible work schedules to seizing unexpected business opportunities to exuding patience and flexibility in the face of inevitable red tape or cultural differences, the lesson is clear:

Be flexible. Chill out. Roll with the punches.

Number 3: Find a Community, Tribe or Support System

All human beings need to be a part of a community in order to really thrive in life. It doesn’t really matter who’s in your tribe or where you find those people, but seek and ye shall find.

As a digital nomad, it also helps to connect with the locals in your current location. It’s that je ne se quoi secret sauce that just makes everything better, no matter where you are. This way you never feel like you’re outside the circle because you’re always in it.

Number 4: Be Clear About Your Why and Stay Honest to Yourself

There’s a lot of talk about this darn “why” out there in business, personal development and academia. That’s because it’s important.

If you don’t know why you’re doing something — whatever it is — then you’ll never know if you’re going in the right direction or climbing the right ladder. Or if your ladder is leaning up against the right wall.

Far too many people enter the digital nomad lifestyle under the hazy guise of wanting to travel, without calibrating their internal compass first.

You’d be surprised how many people try to board the wrong plane. But in real life, there’s no friendly gate agent to point you in the right direction.

Every decade in life is precious. You don’t want to waste a minute or year treading water if you don’t have to. Sometimes 5 minutes of reflection can pre-empt years of anxiety, confusion, and false starts.

If you know why you’re doing this and what your goals are, you can gauge how well things are going for you.

You’ll very likely reach a point when you might decide you don’t want to be nomadic anymore and that’s fine. But if you aren’t clear on that why before you even start, the indecision of today can put precious future years in jeopardy.

Do You

My clients seem to value originality as well. In my little poll, a large number of them responded that they feel comfortable being different. They went their own way, marched to the beat of their own drum, followed their heart and what have you. They trusted their own instincts and desires more than what society suggested, and they didn’t care what anyone else thought.

While this is anecdotal, it’s also a proven way to “beat the market.” Betting against common knowledge and being right is something Ray Dalio espouses in his book, Principles.

How Can You Plan to Succeed as a Digital Nomad?

You got this

1) Determine Your WHY

(See above.)

2) Create a Life Design Plan

If part of the reason you wanted to become a digital nomad was for more control over your destiny, make sure you do just that! A life design plan is a good way to get a bird’s eye view of your master plan and what makes you happy. More than a vision board, it’s a practical way of creating your future with intention.

It should cover all aspects of life like:

  • You personal mission
  • Health & wellness
  • Spirituality
  • Friends & family
  • Finances
  • Fun & recreation
  • Community
  • Philanthropy
  • Etc

3) Reflect on Your Situation Regularly

It’s easy to forget your goals just as quickly as you think of them. You need to keep them at the forefront of your awareness for the best chances of following through.

Whether you do this monthly, quarterly, or annually, it’s important to regularly conduct self-assessments, objectively review your progress, and decide when you need to elevate or discard a past goal. As you travel around the world, meet people, and grow as a person, your priorities might change. YOU might change!

If you’re feeling out of alignment in any of these areas, you might be straying off track. The best way to feel good again is to recognize when and where you took a wrong turn. Then get back to your happy place.

Conclusion:

So, what are the main ways you can set yourself up for success? Let’s recap:

  • Get clear on why you’re doing this before taking off. If you’re running a race, you know where the finish line is. If you’re flying a plane, you know where you’re landing. Be the captain of your own ship!
  • Have a solid understanding of your skills, expertise, and target market so you know your value proposition to the world.
  • Take small steps to test things out and adjust as necessary.
  • Take responsibility for your actions. Be self-motivated and self-directed, while knowing that sometimes (many times) you’ll have to do things you don’t feel like doing.
  • Take a chill pill. Being laid back and resilient are important traits for professional nomads.
  • Bounce back quickly from failures. Expect that things will go wrong — a lot of the time. Murphy’s Law is not forgotten on the nomadic population. It’s all part of the process. Take every setback as an opportunity for growth.
  • Work a lot (or enough). If you find yourself wondering what you did this month and why you didn’t make a dent in your to-do list, you’re probably spending too much time on shallow activities and not enough in deep work mode.
  • Follow a spending plan. Make a budget and stick to it. Make sure you can pay your bills without worrying, going into debt or having to eek out a living from a hostel. Remember that — in many cases — you are your business! A solid financial foundation is like an oxygen mask on an airplane.
  • Get involved with your community. Find your tribe IRL and online.
  • Design a daily routine and take care of yourself. Be kind to your nervous system and immune system. Figure out a set of daily habits or routines you can take with you anywhere in the world so that you can function at an acceptable level and remain in control of your life, career, and finances.

If you’re constantly exhausted, jet lagged, malnourished, or hung over — uh, why are you doing that to yourself? One of the best things about being a digital nomad is having complete control over where you work, how much you sleep, what you eat, etc.

  • Travel slowly. “The journey is the destination” has never been more true. They say it for a reason. Make sure to savor the moment and schedule downtime for optimal work-life balance.
  • Be grateful. What a time to be alive! Being a digital nomad is living the dream. Appreciation makes it that much better.

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Kristin Wilson

100M+ Views | Author of Digital Nomads for Dummies | Host of the Traveling with Kristin Podcast & YouTube Channel https://travelingwithkristin.com/relocation