The Failure of Failing Fast :

A Better Way to Dive into Digital Nomadism

“You’re shockingly well adjusted.”

The words leap from my mouth before I can catch them. Though they’re meant as a compliment, my words are poorly chosen. They’re possibly rude and definitely unprofessional. I’m on the cusp of a breakthrough.

I’d spent the last month interviewing travelers of all kinds, focusing on the extremes: Digital nomads. I learn about their motivations and their experiences. Their successes and their failures.

Over and over again, I hear the compelling, painful stories. The tales inspire, but are filled with words of warning. Life as a digital nomad is not as romantic or easy as it may appear. Becoming one almost never goes smoothly. Often taking multiple attempts before the lifestyle sticks.

This story was different. It seemed too smooth. There were no cataclysmic events along the way. It didn’t paint the idyllic picture of digital nomadism that pervades pop culture and Instagram, but let’s be honest, no one’s life does. Instead, it felt healthy and practical. Almost routine. Almost boring.

The other stories I’d heard felt like they would make for great movies. This one felt like it would make for a great life.

Driven by Discontent

In my research, I’ve found many, if not most, people who decide to become digital nomads decide to take the leap into nomading after experiencing a major traumatic life event. This could be the loss of a job, the end of a relationship, or a religious awakening. A big, scary, and stressful event catalyzes their desire to leave traditional life behind.

These individuals already felt discontented. They were restless. They wanted to travel more. To see the pyramids of Egypt, the beaches of Bali, and the markets of Tangier.

They weren’t happy in their hometowns. Towns that felt small, inconsequential, and out of touch with their values.

They hated their office jobs. Working 8–6 in a cramped, windowless cubicle was just never going to cut it.

They read The 4 Hour Work Week and for the first time became aware that there are other ways to live life. It was inspirational and debilitating; illuminating everything that was “wrong” with their current lives.

The person who becomes a digital nomad doesn’t want to find themselves at age 85 on their deathbed having lived a life of regret. They don’t want to have to pull their grandchildren to their sides and whisper into an ear, “Don’t be like me. If you wait until the perfect time to live, it will never come. Live your life today, because today might be the last chance you get.”

What Would You Do?

Often digital nomads start the journey because they are dissatisfied with their lives and have just experienced a life changing traumatic event. What would you do in their situation?

For these future nomads, the answer seems to be to change everything. All at once. They say goodbye to friends and family, often going on a thank you tour before hopping on a plane to start their new lives. Alone. In unfamiliar places. Perhaps, without a steady source of income. The only tie they have to their former lives is an unreliable internet connection.

Is this an extension of the fast food culture we live in? We want and expect an immediate resolution to every problem we face. We expect to get our way every time. We tell ourselves stories about innovation and success that make us believe that instantaneous, spontaneous change is not only possible, but desirable.

I’m not sure that it is true, in any context. I think most change in the world happens slowly over a long period of time. We just think changes happen instantaneously. We think this because by the time an innovation or cultural change becomes important enough for most of us to notice, it has been developing for years, or decades. For us to notice, most changes have to hit a critical mass that the average person can identify with and understand. The changes are really slow and incremental, not fast and abrupt.

With All Deliberate Speed

I think we should take the same incremental approach to making changes to our lives. If we don’t the results can be disastrous. At worst, aiming for radical innovation in our lives can result in extremely negative mental and physical health outcomes. At best, expecting radical change will leave us feeling disappointed.

In the case of the digital nomad, an attempt at radical change goes something like this:

Step 1: Pre-Launch

You change everything in your life. You get rid of all of your stuff… then buy all new stuff based on a shitty packing list. You hop on a plane to Bali or Berlin. It’s exciting. You’re ecstatic.

Step 2: Launch

You live the life of a traveler on an extended vacation. Everything is new and fascinating. Every day brings new and novel experiences. Moving from place to place quickly, in search of your next fix is fun, but you’re on the travel equivalent of a drug induced bender. You may actually be on a drug induced bender.

Step 3: Life Interrupted

You emerge from you bender feeling exhausted. In six weeks you’ve been through 6 countries, but you don’t really remember any of them. Looking at your dwindling bank account, you realize you should probably get to work. And that 15 pounds was gained eating not like a local, but like an American on vacation.

Step 4: Get to Work

You try to be more productive, but you’re a little lost. No one is telling you what to do, so you have to figure it all out for yourself. There are no constants. No easy choices. Where do you sleep tonight? Where do you work today? When do you work today? What do you eat today? Where do you buy deodorant?

At some point, you realize you don’t actually know how to work and travel simultaneously. The amazing entertainment potential of each new location makes sitting down to get shit done incredibly challenging. Oh, and you have no one to talk to. You haven’t had a meaningful conversation, in person, with someone who cares about you in months.

Step 5: All Downhill from Here

So now you’re broke and alone. You can’t seem to get anything done and you have no one to talk to about it. Anxiety sets in. Everything that excited you before becomes intimidating. At first, you were able to meet fellow travelers with ease, now that becomes unbearable. Even when you do talk to someone, you can’t form a connection. Isolation and anxiety give way to loneliness and depression.

You wake up one morning in a place you don’t recognize on the verge of tears. Using your (or your parents’) last few dollars, you buy a plane ticket home. Boarding the plane with your tail between your legs overcome with dread, you spend the entire flight preparing to face an orgy of critics having to admit defeat. Ready to admit that they were right, that your dream of a better life was foolish, misguided, and immature. At least you’re still alive.

It doesn’t have to be that way.

A Better Way(s)

After speaking with countless digital nomads (and using secondary research to learn from many more), I’ve noticed that successful, long-term digital nomads follow one of two paths. Resiliency or Incrementalism. Neither is foolproof, but I think Incrementalism is by far the better option for most.

Path 1: Resiliency

The first path is extreme resiliency. These nomads go through the process I laid out above over and over again until it sticks. They fail hard, but don’t let it kill their dreams. They know this is a path to the better life and are willing to suffer to achieve it. Every cycle, they learn a few things about life, travel, and themselves that make living as a digital nomad that much easier.

This might work for you, but it’s a risky bet. Will you be resilient enough to keep trying? Will you be willing to face your friends and family after each and every failed attempt? Will you be willing to go back to the life you hated, save as much money as you can just to start the cycle again? I don’t know if I would be.

Path 2: Incrementalism

The second, and seemingly easier, approach is that of incrementalism. This is the story that was unfolding during my breakthrough interview. What it showed me is that there was a better, healthier path toward becoming a digital nomad. Really, a better, healthier way to make any major life change.

Instead of enduring a traumatic event and blowing up your entire life, move step by step. First, repair the damage done by the trauma to whatever extent possible. If you’ve never worked remotely, find a remote job and begin to build healthy working habits. Establish your ideal work life integration.

If you’ve never traveled alone or to unfamiliar places, get your passport and go for a week or two. Don’t go on vacation. Go to try out your ideal everyday lifestyle… and experience some cool shit along the way. Feel what it’s like not to be able to communicate with anyone around you. See if you actually like spending time in these remote lands, not just as a tourist, but as a functioning member of society.

Progressively downsize your belongings. Figure out when you hit a tipping point. Get comfortable wearing the same 6 outfits over, and over, and over again. Then 5. Then 4. Then 3. Move to a new city in your own country where you don’t know anyone to see if you actually like living on your own. Learn the process of moving from place to place in your native tongue.

Over time, you’ll build up the skills necessary to live a happy, fulfilled life as a digital nomad. You’ll learn what works for you and what doesn’t. You’ll do so without risking everything. Along the way, you may even find out digital nomadism isn’t right for you. That’s OK.

A Better Life, On Your Terms

Moving incrementally, you will learn how to live life on your own terms. You will learn what you value and, more importantly, what you don’t. In the end, you might not become a digital nomad. You will probably find a better life for you, even if it isn’t much different than your old one. Even if it is exactly the same as your old one.

The world we live in makes us think that changes should be instantaneous. That radical, overnight success stories are the only ones that matter. But they aren’t real. Success, in anything, takes time, effort, and self awareness. Every step forward comes after multiple painful stumbles.

We should strive to learn and evolve as quickly as is reasonable, not as fast as possible. We do ourselves a disservice by hurtling as fast as possible towards a binary outcome. Failing fast robs us of the opportunity to learn who we are and what we truly value. It pushes us towards irresponsible, unethical decision making. Ultimately, it reduces our odds of success in any venture.

Digital nomads live on the leading edge of our culture. They are trying something new and rebellious in the pursuit of a better life. But we all deserve better lives. If we learn from their successes and failures, we’re much more likely to get there.

I am not a digital nomad. I probably never will be. The theory outlined above comes from design research, not personal experience.

However, learning from nomads has had a profound impact on my life. From their insights, I’ve learned to work remotely, lost 30 pounds in 9 months, dramatically decreased my belongings, and totally reconsidered my buying habits. I am a happier, healthier person as a result.

You may decide the lessons we learn from digital nomads are not right for you, but they are certainly deserve our attention.

Thanks to Taylor Coil, Jenn Sutherland-Miller and Fred Perrotta for their help with this piece. Read their stuff. It’s worth it.

*If you are currently in a position that puts you at risk of physical or emotional harm, you should change that as soon as possible.


On Your Terms is a publication by Tortuga, makers of the ultimate travel backpack.

Source: Medium:Remote Working
The Failure of Failing Fast :

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