The TRUTH About Being a Digital Nomad (Q&A With Josh Rueff)

This is a question I get a lot: “How can I become a digital nomad?”

I love that question, because you deserve to live life on YOUR terms. Life isn’t just about surviving, and I want — from the very core of me — to help you thrive.

BUT, it’s not all sunshine and skittle-pooping unicorns.

Those words — digital nomad — mean more to me than just about anything, and becoming one is a very real challenge, and I’ll tell you why.

Being a Digital Entrepreneur

Remember when those “Work From HOME!” ads were about as scammy as they got? Well we’re not in 1991 any more Toto — digital freelancers and online entrepreneurs are becoming the very backbone of the global economy.

This is why I love being a online entrepreneur and digital nomad.

First, every day is an adventure. Every. Day. Some days I wake up to the sound of frothy white waves crashing on a private beach in Ecuador, and other days I roll out of my tropical treehouse bed to be met by the warming beams of sunlight that found openings through the dense vines and foliage.

Other times it’s a the majesty of the mountain range with spring-fed trout that beckon me, and still other times it’s curious cultures that bustle around the Kerala villa I’ve decided to call home for a month or two.

Then, it’s off to work. It’s not something I dread or get bored with — if that was the case, I just… wouldn’t.

Will I need to eventually, yes! But I can live like actual royalty for less than $1,000 a month here, and I have no boss, mortgage or bills that force me to work when I don’t feel like it.

So maybe today, I’ll put off making a few thousand for another day.

Maybe I’ll go for a refreshing morning swim instead, or fish on the beautiful beach all day as my fiddler crab companions skitter here and there with their pincers held high.

Anyway, enough of that — let’s get to the good stuff.

How can you become a digital nomad today?

In this interview I answered the best questions you had for me — if you have more, let me have it at

When and how did you first learn about digital nomads?

That’s actually hard to say… I think I stumbled on the idea of traveling the world while earning my wages like a digital gypsy in Cuba, as I daydreamed — later I read books like Possum Living and even more relevantly, The 4-Hour Workweek.

It’s funny because before I read books like that, I came up with a nomadic gameplan. I thought “this is brilliant — we can finally quit the jobs we hate and do the things we love, ANYWHERE we want!” See, I thought I was going to revolutionize the world and free them from their misery with this brilliant strategy. Then I read the 4-Hour Workweek… As much as I wish I could say that I’d already developed a plan just as good, I hadn’t. So, like many, I have to credit Tim for inspiring me and getting my strategy organized (although I DID have the idea before I read his book, and my way of doing things is MUCH different to be fair.)

Why did you decide to become a digital nomad?

Digital nomad was never a part of my vocabulary until the last few years of my life. That said, I think I officially became a digital nomad — in heart at least — as I travelled the world in a Marine Corps special forces unit (I think they’re called the Raiders now). There were so many adventures I wanted to experience — so many jungles to explore, warm beaches to nap on, coves to snorkel, languages to learn, and animals to observe. More than anything, I wanted freedom.

I hated how unhappy people seemed with their jobs. Figured there must be something better out there.

The problem was finding a job that would let me travel the world and do what I wanted, whenever I wanted to.

As you’ve probably guessed, there aren’t many traditional jobs like that, so I struck out on my own.

I’ve always had entrepreneurism in my blood — I remember selling fishing bait on the side of the road when I was 6, and lunch subs in junior high.

This time though, I knew I had to make real money — enough to free me for good.

I had been writing from age of 3 or so thanks to my uber-ambitious dad, and other than drawing, it was my favorite thing to do. So that’s what I did.

Writing evolved into content writing, copywriting, content marketing, consulting and speaking engagements.

You talk a lot about freedom — can you tell me what that means to you? 

Absolutely. Most people, like it or not, have let their addiction to safety influence them to enslave themselves to what’s become a societal norm. Sorry I know that’s a weird way to put it —  basically what I’m trying to say is this.

Over 80% of Americans hate their jobs, but willingly work the majority of their waking life doing things they hate.


Because of a steady paycheck. Benefits. Because their parents and education system taught them how to be a good economic asset.

Doing anything else is scary because they might not get paid the same time and day every week. They might not have guaranteed health benefits, or they’ll have to get their own.

Worst of all (and this has been my own experience), their friends and family might think they’re strange birds.

Social acceptance is a huge part of the psyche, and to most people, that’s their biggest fear.

What is freedom to me?

► Freedom is living life on my terms. If I want to pack up and move to Hawaii for a while, I can and I will. I don’t need to ask for time off, and I don’t need to worry about how it’ll reflect me.

► Freedom is waking up at 5 to do my daily routine, then deciding “you know what? I want to sleep in today.” And then doing exactly that.

► Freedom is doing something you love, and getting paid more than doctors and lawyers for it (believe me, it boggles my mind too).

► Freedom is never feeling the need to escape.

For some people, the only thing that keeps them sane is the memory and expectation of the weekend, or looking forward to the one vacation they get each year.

If I can get anything across to you, it’s this — your life doesn’t have to be miserable, and it doesn’t even have to be average!

The truth is, being normal is a lack of courage. 

I’m not going to lie to you and say it’s easy or that you can get independently wealthy in a few weeks. It’s hard. Sometimes it’s a genuine struggle. But in the end, you’ll be FREE.

On that note, what has been your biggest challenges or frustrations?

Great question. I love this question because so many digital nomads like to show off how they work on their laptops on the white sands of Honduras (which is BS by the way — it usually gets waaay too hot for that), or vlog about nothing but ziplining through beautiful tropical forests, eating delicious food and yeah, basically all the good stuff without telling the truth about how hard it can be.

And I get it by the way — who really wants to see the hard things in life, especially if you aspire to be a digital nomad?

Anyway, for me, the toughest thing, hands down is keeping friends. 


It takes a rare breed of person to be okay with their best friend being gone for months or even years at a time, then coming back with the hopes of picking up like nothing changed.

Honestly, I’ve lost many of my best friends because of this lifestyle. If you want to be a digital nomad, you have to find people like you or you’ll never have a social life that as humans, we all need.

Next to that, I’d say overcoming fear. Like all of us I’ve been trained from a ridiculously young age that work is important.

THAT’S not the problem — it’s the definition of work — THAT’S the problem.

School taught us to take orders and do what we’re told — NO QUESTIONS ASKED.

Why? Because I said so. That’s why.

The Merriam-Webster definition of slavery  is:

“submission to a dominating influence.”

What we’ve been taught about work is disturbingly similar. There’s always a dominating hierarchy that we submit to. If we work really hard and get good at what we do, maybe we’ll get to be one of the “dominating influences,” but we’ll always be a slave to someone.

And this is a good thing how? Why aren’t we taught to be autonomous, innovative entrepreneurs who round up enough passive income to retire by the age of 30?

I just don’t understand our system.

Anyway, this is where fear sinks its soul-sucking fangs in.

In a job, you exchange your submission for a regular paycheck and benefits. 

Making the plunge into a freelance or entrepreneurial lifestyle can be terrifying, because at first, you won’t have a regular paycheck or benefits.

At least that’s how it was for me. And frankly, there’s been days when that dull blade of anxiety plunged deep into me — I’m not proud to say it, but there were times when it froze me up solid; paralyzed me with fear of the unknown.

That’s why it took me over 5 years to kick my 9 to 5 job to the curb for good.

But overcoming that fear was the greatest accomplishment of my business life, and the rewards truly are great.

How did you learn how to do it? What resources did you access?

Okay, brace yourself for the lamest, most cliche answer ever.


Do it.

Really, that’s it — you just gotta do it.

Yes, I read some great books on the subject, and yes, I had to find what I was truly passionate about (writing and marketing) and figure out a way to do it online, but to for all the holistic digital nomad advice I give on this website, it all pales next to this simple pointer:

You just have to shove through the “what if’s,” the social backlash, and the fear of the unknown, and just friggin do it.

Sure you should look before you leap, and that’s what this site is for. Stick around and I’ll teach you everything I know about being an online entrepreneur and digital nomad, but don’t let a perceived lack of knowledge keep you from taking the plunge.

You deserve it.


Do Smart People Hate Minimalism?

By Josh Rueff on July 12, 2013

“Simplicity is the final achievement”, Frédéric Chopin wrote. “After one has played a vast quantity of notes…it is simplicity that emerges as the crowning reward of art.”

But not everyone has this opinion on the philosophy of minimalism. Some people hate it.

Some people think minimalism is the devil.

“Hoarding is a human instinct”, said Lord Kames, a leading figure of the Scottish Enlightenment in his Essays on the Principles of Morality and Natural Religion (1779).

“I say more: the hoarding appetite is an instinct obviously contrived for assisting reason, in moving us to provide against want. This instinct, like all others in the human soul, ought to be a cause adequate to the effect intended to be accomplished by it…”

Business Psychologist Peter Shallard says: “The core tenant of minimalism is ‘thou shalt own less stuff’. Maybe it’s my psychological leaning, but this just begs the question:

Why do we own stuff in the first place?

Owning stuff rocks. In fact, owning stuff began with rocks – our caveman ancestors drew a major line in the sand between themselves and animals when they not only started using tools (chimps do that) but started keeping them.
The psychological leap to keep a poking stick or piece of flint (versus finding a new one each day) moves us to the next major brainwave: that one piece of flint is better than another.

Owning the superior piece of flint (cherishing it, even) is vastly more efficient than finding a new flint each day. More efficiency creates more breeding opportunities (less time looking for flint equals more time making babies).
This means we’ve all evolved from the proto-consumers who had the best tools. Our ancestors loved their stuff!” (Why minimalism is toxic for you and your business)
So who’s right?

Plato, Leonardo da Vinci, Benjamin Franklin, and Einstein would side with Chopin (they were all , but that doesn’t necessarily make him right.
Both Kames and Shallard bring up interesting points, but the argument that owning things is important never takes away from the value of minimalism.

Minimalists don’t strive to own nothing.

The purpose of minimalism is to eliminate anything that takes away from the things and activities we value.

If a caveman’s “poking stick” brings him value, he doesn’t became a minimalist if he decides to throw it away. That would just make him an even dumber caveman.

When he hoards too many of those poking sticks (as Kame says is natural and healthy), and ends up carrying a back breaking load of them on his back as a result, he is now in a position where discarding a few would be minimalism. And that would make him a more “evolved” antediluvian ape. (Yes this is sarcasm. Macro-evolution is a moronic theory.)

Minimalism isn’t the devil, it’s (un)common sense.


Dispense of the Indispensable: 5-Minute Simplifying

By Josh Rueff on June 06, 2013

“Most of the luxuries and many of the so-called comforts of life are not only not indispensable, but positive hindrances to the elevation of mankind.”
— Thoreau

Marching to the Beat of a Different Drummer

Thoreau was an extreme individual who wasn’t afraid to march to his own drum.

He received staunch criticism in his counter cultural exploits of the Walden project, but he stood firm on his principles, and we know him and he is endeared to us for this very reason.

His philosophy revolved around the lifestyle balance between nature and cultured society. He preferred to live in the “partially cultivated country” as he put it. Amongst his principles was his opposition to slavery, the Mexican-American War, materialism, corporeal punishment, and corporations.

He was imprisoned for refusing to pay taxes, and he gave up living in civilization to pursue the most simple, back to the basics lifestyle he could, living off of the land on the transcendental homestead he recorded in his book, Walden.

I love extreme “ground up” examples of minimalism because even if I can’t adopt all of the activities, at least I have a blueprint of the possibilities on that side of the spectrum.

I think it has something to do with the difference between dabblers and experts.

An extremist is never a dabbler – unless he’s a fraud.

Not everyone has to embrace extreme minimalism to reap the benefits, but whether you’re an extremist or a dabbler, you’ve got to start somewhere!

That’s where the 5-minute simplifying challenge comes in.

The Challenge

Think of one single item you never use.

Take a moment to embrace the cherished memories and financial value it has brought you, then embrace the reality that it has become utterly worthless. How many times have you used t in the last year? How many times have you even thought of it?

Throw it out, trash it. No ebay, craigslist, or garage sales – disown it completely.

If you have someone you can give it to immediately, even better, but the point of the exercise is to get a foothold in simplifying your life, and the longer the activity takes, the higher the chances are of putting it off for “next time”.

Take a page from the Thoreau mindset and think of this item (and other things like it) as a “positive hindrance to the elevation of mankind”.

Begin your journey to your lifestyle apex; dispense of the indispensable, item by item.


The Freedom of the Underdog: 5-Minute Simplifying

By Josh Rueff on June 05, 2013

The classic underdog story of Rudy moves just anyone with a soul to tears. Braveheart is even better (or worse if you hate showing your emotions).

Rags to riches stories never fail to inspire, and for me personally, it’s just not possible to watch an underdog without hoping they can muster the willpower to overcome the odds.

Why do we have such an appreciation for the underdog?

My first instinct to say that it’s because we can identify with them – everyone’s been an underdog at some point or another, and most of us probably feel like an underdog right now.

In this study psychologist Joseph Vandello shows how people will always root for the underdog by observing how people took sides in the Israeli-Palestinian conflict. When Israel was portrayed as the underdog, people expressed sympathy and support for them. When Palestine was portrayed as the underdog, they supported them.

Whether our support is rational or irrational, underdogs always have one thing in common; one trait that moves us all to empathize and cheer them on.

The common trait is freedom.

They always have a “bigger” oppressor, and that antagonist is usually symbolic of a more important internal conflict with a more abstract enemy like fear, social status, or some kind of emotional, mental, or physical weakness. 

When the underdog overcomes, he hasn’t simply beaten a better football team, or out boxed a superior fighter; he’s earned some form of freedom from the oppressors he fights against.

And that’s precisely what we relate with.

We all have our own deeply personal enemies: Fear, social boundaries, poverty, debt, addiction to safety, invisible ceilings, lack of appreciation, emotional scars from the past – we have so many enemies to conquer. And it’s time to do just that!

The Challenge

Take 5 minutes out of your day to define – define – define:

1. Define Freedom.

2. Define your enemies.

3. Define what Minimalism is to you.

The first steps to winning any fight are:

1. Knowing your opponent.

2. Having the motivation to fight and overcome that enemy.

3. Developing a strategy to win.

There are many paths a Minimalist can take to overcome, and for me this has been the most effective route to victory.

Good luck and I hope you win your fight! 


A Minimalist Struggle for Freedom

By Josh Rueff on June 05, 2013

What is freedom exactly – and what does freedom have to do with minimalism? Am I – A citizen of a nation forged upon the foundation of freedom – Am I truly free?

Mankind’s Perpetual Struggle for Freedom

It is 1783, a year of moral victory for the newly birthed nation of America. Benjamin Franklin eyes were bright and his mind sharp, despite an aging body, 77 years in the making. His hand shook slightly as he pressed the quill to paper, writing a letter to a Benjamin on the other side of the war – Benjamin Vaughan, a commissioner of Britain between the negotiations for the drafting of the treaty of Paris.

Slowly but deliberately he wrote:

“Where liberty dwells, there is my country.”

Over 200,000 Americans believed so strongly in the importance of liberty that they fought a war to gain it, an estimated 40,000 dying in the effort.

Striving for freedom isn’t unique to the colonists in early America – mankind has always disdained any form of oppression or slavery, and will always strive, tooth and nail, to maintain the highest degree of freedom.

This list is just a small scratch on the iceberg of wars, uprisings, battles, and coups fought for freedom:

508/7 BC: The Athenian Revolution establishing democracy in Athens.
464 BC:The Helot slaves revolt against their Spartan masters.
73–71 BC: The failed Roman slave rebellion, led by the gladiator Spartacus.
66–70: The Great Jewish Revolt, the first of three Jewish-Roman wars that took place in Iudaea Province against the Roman Empire.
248: Lady Trieu Uprising of Vietnam against Chinese Domination
713: Mai Thuc Loan Uprising of Vietnam against Chinese Domination
817–837: The revolt of the Iranian Khurramites led by Babak Khorramdin.
869–883: The Zanj Rebellion of black African slaves in Iraq.
1250: The Mamluks killed the last sultan of the Ayyubid dynasty, and established the Bahri dynasty.
1497: The Cornish Rebellion of 1497 in England.
1514: A peasants’ war led by György Dózsa in the Kingdom of Hungary.
1515: The Slovenian peasant revolt.
1549: Kett’s Rebellion.
1573: The Croatian and Slovenian peasant revolt.
1642–1660: The English Revolution, commencing as a civil war between Parliament and the King, and culminating in the execution of Charles I and the establishment of a republican Commonwealth, which was succeeded several years later by the Protectorate of Oliver Cromwell.
1791–1804: The Haitian Revolution: A successful slave rebellion, led by Toussaint Louverture, establishes Haiti as the first free, black republic.
1848: The French Revolution of 1848 led to the creation of the French Second Republic.
1916–1923: The Irish War of Independence, the period of nationalist rebellion, guerrilla warfare, political change and civil war which brought about the establishment of the independent nation, the Irish Free State.
1918: The German Revolution overthrows the Kaiser; establishment of the Weimar Republic.
And of course:
1775–1783: The American Revolution establishes independence of the thirteen North American colonies from Great Britain, creating the republic of the United States of America. (Class wars: Source.)

I find myself pondering on the meaning of liberty, or freedom as we more readily call it today. I’m grateful for the many freedoms I’ve been born into, without risking my life to gain them, and I’m thankful for gall and courage of the men who readily did.

But I’m still restless, and even wary, as though something or someone has breached the fortification that holds the treasure of my freedom.

Am I really free?

What is Freedom – Am I Free?

There are two extremes regarding freedom:

On one end, I am a slave with no liberty – I own nothing, have no power of choice over my own actions, and I am nothing – except another man’s property.

On the opposite end, I am completely free. I’m held back by nothing – I can do whatever I want, whenever I want, to whomever I want, with no fear of repercussion.

So on one side I’m a slave, and on the other, a king.

Initially, the concept of being a king is somewhat off-putting; I need checks, accountability, and regulation to keep me from exploiting others right?

Or do I?

When it comes to government, I see the need – I don’t want anyone to have that kind of freedom unless I trust that person with my life, and yet for myself, I would be happy with accepting that kind of freedom for myself!

And I doubt that I’m the only one, but the fact is, I’m not that free, and I never will be unless I buy an island somewhere and name myself king of my new country (slightly tempting I won’t lie).

So in the extreme sense, no I’m not 100% free. I’m bound by laws and regulations.

Since the penalty for living in a civilized nation is law and regulation, what level of freedom should I be satisfied with?

This answer varies widely from person to person, and that’s why defining freedom is impossible.

But for myself, I’m happy with the freedoms I have as a US citizen (for the most part) – it’s not oppression of government that I fight against, but against the oppression of a far more subtle enemy.

What Eliminates Freedom From My Life?

The patriots and the groups above fought against a human oppressor. As minimalists, we fight against anything that limits our freedom, especially regarding time and money.

Anything that burns away time needlessly or without a good enough reason is the enemy.

Anything that pulls money out of our pocket needlessly or without good reason is the enemy.

What kills my time, and what kills my money?

1. Debt: This is perhaps the number one inhibitor of a person’s freedom, regarding both time and money.

A person with accumulated debt has to make choices that they don’t like and don’t want (working long hours, working in a career or job they dislike, etc). These stressful choices are ultimately forced upon them by debt, which has become a form of slavery because it robs the person of a number of better choices and forms of lifestyle.
2. Controlling Relationships: A man or woman that grasps for control in a relationship is in danger of enslaving his or her partner. This typically results in a break up because of the human instinct to fight for personal freedom, but there are people who essentially become a slave to their partner in the sense that they have no control, and the other person does.

Their freedom to make decisions is taken away, and this absence of freedom is a form of slavery that kills the valuable commodity of time.

3. Jobs and Careers: This is a sore spot for most of us – we’ve all worked at jobs that we hated, and put up with poor organization, management, or some form of inadequacy that made our lives miserable for a period of time.

Statistically you’re probably still in that position, dying for a chance to get out of your chosen job or career, while silently accepting the fact that you’re stuck – This inability to change careers to improve your lifestyle has made your job/career the “master”, and robbed you of the freedom to make a more fulfilling decision, and in a sense you’ve become a slave to your position. You can earn money just about anywhere doing anything – it’s up to you to choose what work is worth it.

I don’t consider time spent working on something I’m passionate about a job. It’s work, but it’s fulfilling work. On the other hand, if I hate my job, the money I earn isn’t worth the time it steals from better things. I can earn money just about anywhere doing anything – it’s up to me to choose what work is worth it.

These, like the list of freedom fighters, is only the tip of the iceberg.

The Minimalist Revolution as many call it, is the counterattack to these threats, and many more.

I’ve spent many years of my life fighting for my freedom, and so far it’s paid off well, but there’s many more battles to be won. 

The resounding question I continuously return to is: “How?”