The Dirty Truth of Being a Digital Nomad Entrepreneur

Warning + Disclaimer: Shit is about to get really real. I’m definitely experiencing a little 6 month slump of this year-long experiment. That’s okay. It’s bound to happen to even the most experienced travelers and I’ll be out of it in no time. But it’s the perfect opportunity to share some harsh realities of living the digital nomad dream.

LOCATION: Valparaiso, Chile

In a professional and entrepreneurial landscape — and a Facebook ad targeting and retargeting juggernaut — it would seem that the best path, the elite path, and possibly the only path to happiness and success is to sell everything, pack your bags, grab your laptop, travel the world, and build your business from the road.

That’s what the gurus and the ads are telling me every damn day.

The idea of bouncing from country to country, cafe to cafe, getting paid to go where the flow of life and amazing local festivals take you — well damn. It sounds pretty perfect. Check out the hashtag #digitalnomad on instagram and you’ll see this lifestyle through a technicolor lens that portrays a land of adventures, beautiful beaches, perfect sunsets, stunning skylines….all while looking over the screen of a laptop with a cocktail by your side.

(And yes, I’m completely, 100% guilty of this myself.)

Don’t get me wrong. The past 6 months have absolutely been a transformative privilege and adventure that’s bound to make some appearances in the memoire I’ll write someday. It’s gonna be lit! ;) But that’s not what this article is about.

You can find plenty of resources and people selling you on the idea of becoming a digital nomad. They all have great advice and wonderful perspectives. I support it and you if you choose to accept the challenge and claim your digital nomad badge. Because believe me. It’s not for the whimsical and faint of heart. You need some cold hard facts and truth bombs before you take the leap. So here we go.

THE PRESSURE OF 24/7 YOLO

If there’s one thing that most attracts people to the digital nomad experience is that you can find yourself in far corners of the world in the backyard of some of the most incredible sites and experiences that consistently land on those “top places to visit before you die” lists.

And when you find yourself in one of these locations, the pressure to go, see, do, taste, touch, smell, hike, experience whatever it is can be overwhelming. YOLO, BABY (you only live once)!

Of course, in an ideal world, you’re not a digital nomad. You’re an independently wealthy heiress with unlimited funds and time. So jaunting off to the next wonder of the world or top ranked restaurant or rarely visited region would be a no brainer.

But when you’re working, running/launching a business, AND have finite funding, those things just aren’t realistic. I’m not paid to travel. I’m not paid to blog or make videos about my travels. I make ZERO dollars from traveling. I pay for it with my own money that I earn from doing my real work. Work that requires typical working hours, high-speed/reliable internet, meetings, focused time to execute on projects, etc.

[Note: If you want to get paid to travel and write blogs and make videos, awesome. That’s called influencer marketing and that’s not what I do or the kind of business I run.]

For instance, the yearning to jaunt off to Patagonia for a week is killing me a little inside this month in Chile. I’ve dreamed of hiking those mountains, seeing those glaciers, exploring it all for a long time. And, yes, I have the common thought of: “I’m already so close! I’d be losing money if I don’t make it happen while I’m here! The work can wait! YOLO, BABY!” But that kind of thinking is similar to seeing a big sale at Nordstrom and thinking “I’d be LOSING money if I didn’t buy all this stuff.”

Just because it’s so close doesn’t make it feasible. Even if money wasn’t an issue, there’s still the even more limiting element of time.

Which leads me to….

I’M NOT ON VACATION

If the constant feeling of YOLO comes from the inside, the constant pressure of FOMO (fear of missing out) comes from the outside. I get messages and emails every week from wonderful people with amazing travel experiences eager to tell me all the big trips and things I can see in any given country I’m in.

And believe me, having worked in the travel industry for so long, I know some very well traveled people. Their advice and insights are invaluable! And if this were merely a vacation, I’d be planning my experience within an inch of those suggestions.

But, sadly, that’s not my reality. Big multi-day trips that take nearly a week of work and productivity for travel time and seeing the local sites aren’t feasible. I couldn’t take week-long vacations every month while I was living in Kansas City, and I can’t do it as a digital nomad.

You might be thinking: “But Brooke. You’re location independent! Take your laptop on these side trips, explore during the day, and hustle at night!” That’s an awesome idea. And I’ve done it a lot! It can be great. But like most people, when I go on vacation, I want to really turn off and tune out. The mixing of hammocks and hustle sounds great and makes for a lovely Instagram pic, but rarely results in massive action and making big moves in your business. Most of the digital nomads I know are simply staying on top of email when they mix vacations and work like this.

It’s when we plant ourselves in one spot for awhile, focus on our biggest most important tasks and projects, and live a relatively “normal” day (in a cool city) that the real work happens.

When you mix your work and adventures, something always takes a hit. Either the work isn’t that great or the adventure feels stifled.

“SERIOUS ENTREPRENEUR CAN’T BE DIGITAL NOMADS”

Here’s the deal: You do not need to be an entrepreneur to be a digital nomad. There are many ways to make a living and travel the world including being a freelancer or getting a remote job with an established company. These are both amazing options and I’m traveling with several people who are doing this and excelling at it.

But the entrepreneur path as a digital nomad is a little different. The same kind of financial and performance pressure exists while you travel as an entrepreneur as when you’re settled, but when you’re traveling, a new level of scrutiny and pressure emerges.

And it seems the underlying belief of non-digital nomad entrepreneurs is that you can’t have two main priorities: travel and building a business.

There seems to be a stigma that it can’t be a real focus or it can’t really grow if you’re not settle in one place. Here’s what I’ll say about that: If #1 and #2 are a constant source of strain and challenges for your business, then being a digital nomad could be a death sentence to your business.

You have to be able to say no and also buckle down and get shit done (even if your friends are drinking pisco sours at the beach watching the sunset in Vina del Mar, Chile, while you write this article). #truestory

TIME ZONES ARE A REAL PAIN IN THE ASS

Where you decide to travel and set-up shop any given week or month is going to play a huge role in how you approach your business and your work. And depending on where your primary audience and client-base will be, you’ll have to pay close attention to how the time zone difference will impact your work.

If your audience is in the US and you plan to hop around Asia for a year, well, prepare to have a lot of 3am meetings, monitoring your community at midnight, and generally seeing the moon more than you see the sun.

Not to mention that even with all the technology to help us convert time zones and automatically keep you on schedule and in the right place at the right time, it’s bound to let you down. I missed one such important meeting while I was in Japan and it was a huge loss for my business.

It seems like a small and obvious thing, but my digital nomad comrades who have sales jobs or teaching jobs where they have to work US or European hours, had really messed up schedules. And combine that with #1 and #2, well most of them didn’t sleep much for the four months we were in Asia.

NOTHING IS EASY WHEN IT COMES TO ELECTRONICS

I’m traveling internationally for a year. I have no real plans to return to the US until likely September or October. Luckily running an online business doesn’t take much technology — I just need a laptop, a charging cable, an adapter, some earbuds, and a smartphone. If I want to get really fancy, add on a microphone (for my podcast), a DSLR camera for videos, an external hard drive for large file backup, and some noise canceling headphones.

But all of that fits in a small backpack. It doesn’t take much.

The problem is when anyone of these items decides to get lost (i.e. I get careless and forget it in another country), simply wears out from use (my MacBook cord is starting to fray and scaring me to death), or gets damage from all the constant moving around.

Back home in the land of Amazon Prime, I can have a new one the next day.

In most other countries, that’s not the case. Whether it’s because the mail system isn’t so reliable or because you don’t have a real address to receive packages or they just don’t sell camera battery chargers for Canon in Vietnam (true story) or because there’s a 50% tax on all electronics…getting the stuff you need to run your business effectively can get precarious.

I’ve had multiple things muled to me from the US in the past 6 months for the simple fact that I didn’t want to pay double for a knock off brand, I was moving too quickly for it to reach me, or I just couldn’t find it locally.

Granted you might think this is a “first world” problem, but it’s a reality of the digital nomad experience you need to be prepared to tackle.

Am I loving this experience? Absolutely. Does it come without challenges? Hell no. What does?

The digital nomad experience for entrepreneurs requires focus, drive, and most importantly, discipline. You have to know when to work hard and when to play hard. You have to say no to some “classic travel moments” so you can say yes to growing your business. You can’t phone it in when you’re the cornerstone of your operations and the success of the company.

But if you can figure out that special digital nomad entrepreneur algorithm that balances discipline, execution, and adventure, this type of experience can provide just the right combination of inspiration, insights, and drive that will give you a competitive edge.

Both you and your business will see new levels of success.