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

the truth about digital nomads

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.