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4 Harsh Realities Of Working As A Full-Time Digital Nomad


That was two beach-side Mai Tai’s touching rims in case you didn’t know.

I’m on a beach with my laptop writing, staring out at the teals and dark blues of the ocean in between sentences.

This is the life for us remote workers.

We bring our laptops to the beach with us and order drinks right when we get here. The wi-fi is always strong, too.

Trust me.

It’s glamorous, sure, but we’re still not driving around in Bentley’s and Ferrari’s like so many other “successful” people. We’ll take this simple life by the beach any day.

There’s a big problem with this, though.

It hardly ever happens quite like this. In case you didn’t know, there’s no wi-fi directly on any beach anywhere — especially in Southeast Asia where many Digital Nomads go.

I was lying to you with my story. I’m sorry.

Yeah, this remote lifestyle can be glamorous, adventurous, and a lot of fun, but too many people boil it down to that.

The reality is this freedom brings a whole lot of problems with it. You’ve heard the saying “more money more problems?” There should be one like:

More freedom more problems.

I recently sat down with Kate Smith of The Remote Nomad (featured on CNN, HuffPo, etc.) to talk about challenges facing remote workers.

There’s quite a few you might not have thought of:

1. It’s Not Going To Happen All At Once

We’ve all heard that old tale of people quitting their job in an instant, booking a plane ticket to somewhere crazy, and sitting their butt on a beach in Thailand for a couple years, right?

It all seems like it was some spontaneous decision, and that it all worked out fairly easily for them.

To be honest with you, that’s a trick that many of us in the media try to pull to make it all sound more adventurous.

Sure, there are moments when people do quit their jobs AND buy a plane ticket, but that decision isn’t made willy-nilly. The desire to do more marinates inside the soul for a while before it’s acted on. Kate explains:

I was living downtown in the city, working as a project manager at an ad agency. That’s when things changed for me. I remember being in the condo that I was renting and thinking ‘This is everything I’ve ever wanted, why am I not happier?’

I realized that I was working to live so much that I never had the opportunity to travel, you know?

Kate Smith

I came to my realization not as soon as yourself and other people — I felt pretty sure about myself when I was in school for business, but after that I realized it wasn’t what I wanted.

It was a long process that lead me to this Digital Nomad lifestyle and a series of different things happened that changed my perspective.

2. There’s No Real “Road Map” To Success

How many colleges teach you how to be a remote worker, or even just a freelancer? Probably not that many, if at all.

And why should they? It’s really not their responsibility. They’re there to teach you HOW to DO things, not how to LIVE.

Another major gap is the fact that many schools don’t exactly teach anyone HOW to get a job. This means if you’re looking to become part of the remote workforce, you’re kind of screwed on how to actually accomplish it.

It’s up to you to find out by yourself.

Kate explains:

“For most of my life it was do A and get B. Go to University and get a job. It was very black-and-white straight forward with how you need to achieve things. So I had a lot of opportunities and a lot of cool things that happened in life because I did this and got that.

But it was interesting because when I started this [digital nomad] journey it was actually quite difficult. I remember times when I was like ‘I’m trying so hard, I’m doing everything I should do, why is this not working?’ Part of that is there’s really not a roadmap to make this happen.

For me it was a bit challenging.

Yes, I was very hard working and I knew I wanted this lifestyle, but even though I was doing everything I could possibly do, it wasn’t giving.”

3. The Timing Is Never Right —You Just Have To Jump

I’ve written about this so many times before. It’s the hardest part of being a digital nomad.

The jump.

You’ve thought about it, semi-acted on it, but now you either have to purchase that plane ticket or put in your two weeks notice.

There isn’t a perfect day to do this, though. That’s the problem. So much can be up in the air at any given time that you just have to do the damn thing or not.

“Many people would say ‘Oh the time isn’t right because I need to pay all of those student debts off and what not first, but if I waited until that point, look at all the things that wouldn’t have gotten done.’

You have to make it the right time. And for me I push my boundaries and limits in so many ways. When I started my Nomad journey, it was probably not a financially comfortable situation for me to be in, but I did it anyways. Most people would’ve said “I’m gonna save up for six months or a year.”

You can overwhelm yourself with information online, but you just need to do it. Don’t think you need to read these 50 books and take these 14 courses and then ‘I’m qualified!’ There is no qualification, it just happens.

I applied for remote jobs for months without any luck. I booked a one-way ticket and my laptop died right away which is my lifeline.”

4. You Have To Really Want It — Or Else You’ll Fail

I got off the phone with a new friend of mine who works remotely the other day. He said he had to come back home after his trip abroad because it was just a little too hard on him.

I understand where he’s coming from.

I’m currently taking a hiatus from traveling so much to spend time on my blog and book.

The point is this lifestyle is harder than it looks. It takes a special kind of individual, which Kate can definitely confirm.

“You just have to know if you want it bad enough. If you want it bad enough it will happen for you and if you don’t want it bad enough you’ll find an excuse. It’s as simple as that.”

When I first started, I was having trouble finding a remote job, so I just said ‘Alright I’ll book the plane ticket and see how it works out,’ and then my laptop died. So it seemed like there were so many elements that were working against me. That’s why I think you really need to want it — this lifestyle.”

There’s so much that can go wrong on the road. Before you become a digital nomad, just know how tough it really is. I wish you the best.

Get the rest of my interview with Kate in the free 66-page Post Grad Survival Guide Magazine.

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Tom Kuegler

Tom Kuegler

Travel blogger. 29 years old. Currently in Mexico. Get my free 5-day Medium course via email → https://bit.ly/35yyIIu