11 of the Most Important Lessons Learned in 15 Years as a Digital Nomad

Kristin Wilson
Oct 16, 2018 · 11 min read

Travel: it’s invigorating, it’s exhilarating — it’s effing fun. Traveling helps us live in the moment and feel alive as we get to know new people, places, and cultures outside our comfort zones. It also serves as an effective real-world classroom and a solid reality check.

I’ve been traveling, living, studying, or working abroad in some capacity since 2002 and now find myself at “home” within the digital nomad movement. Over the years, I’ve noticed that traveling while working for yourself can increase both the frequency and intensity of formative life lessons.

As a long-time entrepreneur and expat, here are 11 of the most fundamental insights I’ve gleaned from 15 years in 55 countries.


1) Your Plan Is a Jumping-Off Point for Negotiations

I’m not sure how many times we all have to learn this lesson, but it’s a recurring theme in life. The rule of thumb for digital nomads, anyone who’s ever planned a wedding before, and probably everyone else is:

Everything will take twice as long and cost twice as much.

As we learn to expect the unexpected in life, it also becomes apparent that most of the things we worry about never come to fruition. This is a strange human paradox. My strategy to deal with it revolves around these primary points:

A) Plan some, not too much;

B) Leave room for changes and universal magic, as there’s always a wildcard you haven’t thought of yet;

C) It will all work out in the end.

“I’ve known a great many struggles in my life, but most of them never happened.” — Twain, Churchill, Jefferson (and also everyone)

So — whatever you’re obsessing about planning at the moment — take a deep breath, keep these things in mind, and let go a little.


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2) The Little Things Matter Most

Pursuing your bucket list dream of bungee jumping in Africa is all well and good, but,

a bucket list is still a to-do list in some form.

I’ve learned from experience that stopping to smell the flowers can sometimes be more meaningful and fulfilling than achieving your loftiest goals.

Witnessing a good deed by a stranger on the street, stealing a kiss, admiring a sunset… The best parts of life are made up of millions of tiny moments that tend to happen organically.

Even after traveling a large part of the world, I’ve come to cherish simple pleasures like people watching from a cafe, curling up with a book, or melting into a long hug.

Don’t get me wrong — wine tasting in Italy and glacier hiking in Iceland are also cool. But your peak life experiences might not necessarily equate with cashing a huge signing bonus, climbing Mount Everest, or nailing a TED Talk. Some of the best times could end up being decidedly “boring.” Like a Netflix binge on a rainy day or sharing a laugh in your family’s chat group.


3) Material Things Are Bullshit

Everyone would like to win the lottery and never have to worry about money again — in theory. But humanity has to stop chasing wealth as the antidote to sadness.

Stuff is just stuff, which can quickly turn into baggage.

Buying things brings temporary satisfaction, but purging them feels way better. You can’t buy happiness. We know this, but still lose sight of it on a regular basis.

I have a Mercedes that I never drive and a closet full of clothes that I never wear — because it’s more fulfilling to travel around the world living out of a suitcase. Keeping up with the Joneses is a waste of time and energy. Your most vibrant memories in life probably have to do with people, feelings, and experiences rather than gifts, places, and possessions.

This applies on a global scale. To determine a country’s level of happiness, researchers at the World Happiness Report look at much more than just money. They consider six different variables: GDP per capita, social support, life expectancy, freedom to make life choices, generosity, and freedom from corruption.

Money is an essential factor in life, but it’s one of many. Don’t give it more weighting than it deserves.


Photo by Nischal Masand on Unsplash

4) Expanding Your Worldview Is Crucial

If you distance yourself long enough from where you were born and raised, your perspective on your home country and its political system will evolve. With this comes an increased capacity for empathy (always a good thing).

The first foreign country I lived in was Costa Rica, back in 2002. It turned out that 20 years of Sunday school, family dinners, extracurricular activities, and team sports had left me with a pretty narrow and entitled worldview.

It was only when I moved abroad that I realized — holy shit! — I’d been living in a bubble.

Because I grew up in middle-class, public-school America, I used to think that people could be or do anything they set their minds to. But if you’re born in a Nicaraguan slum, the odds are stacked against you, to say the least.

If you’re fortunate enough to travel internationally, you’ll eventually realize that you won the life lottery.

Travel long enough, and you’ll also realize that everything you thought you knew is inaccurate to an extent. People tend to form opinions and religious beliefs based on where they’re born, rather than what’s morally right or objectively true. You’ll begin to suspect that your history books didn’t tell you all sides of the story and that your government is more corrupt than you originally thought. You’d be right.

It’s a small world, but it’s also a complex world. You just have to do your best at interpreting what you see, read, and hear, and keep an open mind.


5) There’s No Right Way to Live

If there are >7 billion people on the planet, then there are more than 7 billion ways to live, none one of which are right or wrong (unless you’re hurting someone, of course).

Life isn’t perfect, anywhere. Everyone is struggling in some way, and no one knows what they’re doing. People might mean well when they give advice, but they probably don’t know what’s best for you (or even for themselves).

If you live in a place where you have the freedom to choose how you live your life, take that and run with it. Don’t worry about what anyone else thinks. You’re a unique snowflake with your own ideas, thoughts, and perspectives. There are generally suggested or expected ways to live, depending on where you’re from, but that doesn’t mean you should drink the Kool-Aid. On the same note, think twice before trying to control what anyone else is doing. It’s better to lead by example. Live and let live.

Many people meander through life, waiting for retirement to provide some kind of closure or clarity. But they would be better served if they came to terms with what they wanted to do sooner rather than later.

In fact, the sooner, the better. The more decisions and actions you take, the more things will happen in your life.

Create your own opportunities and don’t put arbitrary limits around what’s possible for you.


Photo by Nicholas Green on Unsplash

6) Human Beings Are All the Same, but Different

People always ask me what my favorite place to visit is, but I never have a good answer. A country is a benign entity. A nation’s identity and personality come from its’ citizens and what they create.

At face value, some places have more positive than negative traits and vice versa. But the people who live in each country are still human beings.

There are a few shared pillars of the human experience, such as understanding the full range of emotions, speaking a language, working, and relaxing. We all like to eat, sleep, party, have sex, laugh, spend time with friends and family, make stuff, figure things out, complain, gossip, procrastinate, be alone on occasion, play games or sports, make money, and accomplish things.

We all like a good story. We like to be entertained, we fight sometimes, we each have a favorite animal or color, we’re prone to addictions and wired to crave caffeine, sugar, alcohol, carbs, and other substances. We can all relate to wanting to gain or lose weight, or get in shape. The list of things we have in common as humans is endless, yet so much of our public dialogue is divisive.

When we highlight our similarities instead of our differences, our worldview can be wholly transformed.

We are part of one global human race: different colors, different cultures, different foods, different religions, different political systems… But when it all comes down to it, borders are imaginary lines in the sand. People are the real deal.


Photo by Ricardo Resende on Unsplash

7) Everything Is Polarized or Balanced

There’s right and left, darkness and light, the North Pole and the South Pole. If you’re not asleep, you’re awake. Everything has a reference point or a polar opposite. A word must have a definition attached to it. This is a weird universal truth, and I’m not sure what it means in practical terms, but it’s a thing. Everything is related or connected to each other.


8) It Always Works Out in the End

The older I get, the more I tend to forget about things that bothered me once upon a time. Sometimes a friend asks if I remember when… blah blah blah… but I don’t. So much stuff happens on a daily basis, especially in modern-day life. It’s almost incomprehensible.

People have to deal with shit sometimes. Heavy shit. We all do. But if you stick with it long enough, you’ll come out the other side. The only constant is change. Nothing can stay good or bad forever.

“In times of pain, when the future is too terrifying to contemplate and the past is too painful to remember, I have learned to pay attention to right now. Each moment, taken alone, was always bearable. In the exact now, we are all, always, all right.” — Julia Cameron, The Artist’s Way


Photo by Oskars Sylwan on Unsplash

9) Everything in Life Is About People

It’s critical to maintain healthy relationships others in your community, family, and social circle. This is applicable on a macro and micro scale. From our global home, down to our respective neighborhoods— we’re all in this together. You can’t go it alone. At least not forever. You’ll need help, and lots of it, along the way.

There’s a reason that one of the worst punishments we dole out as a society is solitary confinement. Humans need one other to thrive, and everything works better when we work together. That’s just the way it is.

We’re traveling through space on a spinning planet, working alongside each other every day to contribute something to the world. It’s pretty cool when you think about it.

But life isn’t about our stuff or even about our work. It’s about experiences and how we relate to others. When push comes to shove, humans rise to the occasion. We see proof of this every time there’s a natural disaster or global emergency.

Helping and appreciating one another makes life better. It makes the world go ‘round.

“This is what we’re here for. Born out of the belief of worldly interconnectedness — that everything in the universe is part of a larger whole, bees of the same hive — the Stoics established the importance of kindness, of perpetuating abundance by doing good for others, by paying it forward.” — Ryan Holiday, The Daily Stoic


10) You Shouldn’t Wait to Start Living

Life can change in an instant. It can, and it does. There’s no reason to postpone your best life. Try to take tiny steps or make marginal improvements in your life every day.

You don’t have to have it all figured out. You just have to know what to do next. Or have the guts to try something in the face of uncertainty. Writer Benjamin P. Hardy always says that if you aren’t embarrassed by who you were 6 months ago or a year ago, then you’re not challenging yourself enough. He also notes,

“If you want to achieve big things, your path will be unclear and hazy.”

So own it. Don’t wait for permission. Go. Do. Be. Create. ASAP.


Taking in the magic of a Norwegian fjord (2016)

11) Nature Is Pretty Fucking Cool

The older I get and the more I travel, the more amazed I am at how nature works.

Earlier this year, while visiting Bulgaria, I discovered bees, flowers, and foods I’d never even seen before. Then, on my way to the U.S., I sat with my face plastered to the airplane window as we flew over Greenland — mesmerized. Technology is pretty cool, but nature is mind-blowing. Nature is the best.

The more you connect with nature, the easier it becomes to derive meaning in life and feel a sense of gratitude for your place in the cosmos.


Amsterdam, 2018

Final Thoughts

While age is the great equalizer and bestower of wisdom, there’s something about life as digital nomad that provides another layer of perspective to one’s existence on planet Earth. After a few years of location independence, it’s easy to feel like an almost stateless citizen.

When you don’t have as many opportunities to identify with a team, a company culture, or a country, you start to see things from a new angle.

This is one of the outcomes I appreciate the most about being a digital nomad. I’m always amazed and humbled by life and the things I learn along the way.

Just remember that life is what you make it. You’re in charge of what you do, how you live, and how you react to the many things you cannot change.

You have more power than you think. Everything that happens in life is the result of an action or a decision.

Once you remove any limitations to your thinking and creativity, nothing can stop you. That’s when the world becomes your oyster.


What about you guys? What is the biggest lesson you’ve learned in life and did it come from age, experience, travel, or something else?

Want to stay in touch? Feel free to join my group for aspiring digital nomads: Long-Term Digital Nomad Success

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by + 378,907 people.

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Kristin Wilson

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Technology, remote work, and personal growth through travel. Insights from 15 years in 60+ countries. YouTube.com/DigitalNomad

The Startup

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