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The Pros and Cons of Running a Business While Traveling

By January 28, 2021November 23rd, 2023No Comments

Today’s article is by Mitch Glass—owner of the blog and YouTube channel, Project Untethered. He teaches freelancers and solopreneurs how to live a life untethered and make a living anywhere in the world. With the current pandemic landscape, we’d just like to remind readers to stay up-to-date with the current global COVID-19 protocols as well as the travel restrictions that apply to their specific country and area.

Running your own business isn’t easy, but it comes with its perks.

One of those perks was the ability to travel—something we’re all looking forward to again in the coming year.

In this article, I’m sharing my pre-covid experience of running my business while getting to explore the world. With more and more people given the opportunity to work remotely, this can be the next step in your entrepreneurship or career to look forward to!

Running a Business While Traveling

If you are a freelancer or can manage your team remotely, you could technically do that from anywhere on earth (with an internet connection, of course).

But just because you can do something doesn’t necessarily mean you should do it.

I’ve been working my way around the world over the past 5 years, and it’s a lifestyle I wouldn’t trade for the world. That said, it’s definitely not all rainbows and butterflies. 

Today, I want to share with you some of the pros and cons to help you decide if a digital nomad lifestyle is for you.

Let’s get those pesky cons out of the way first.

The Cons

Finding a work-travel balance

The hardest part of running a business on the road is balancing work and play. 

Not many people realize that travel planning is like having another part-time job. You constantly have to figure out…

  • Where you will sleep tomorrow
  • What mode of transportation will you take to get there
  • Where to find the best deals on tickets to your next destination
  • What are the “can’t miss” activities to do in that destination
  • How to buy a SIM card and load it with data
  • Where there is wifi
  • Where are you going to wash your clothes
  • Where are you going to exercise
  • Etc.

All these things eat up your schedule. 

Because of this, it’s impossible to give your 100% to anything.

It’s hard to fully enjoy a location knowing all the pending work you need to finish.

And it’s hard to fully focus on work when you want to explore everything at your destination (who knows if you’ll ever be back!). 

What’s the point of traveling the world if you’re just going to sit in your hotel behind a computer screen?

Keeping your belongings (and yourself) secure

When you work online, your digital nomad laptop is your financial lifeline. And it can be nerve-wracking carrying around such expensive equipment. 

It’s like traveling with a baby. You’re always worried about keeping it safe—from getting lost, getting stolen, getting wet, getting dropped…

There will always be lingering anxiety about the safety of your equipment.

These worries can be remedied by choosing “safe” locations and “tame” activities. But what’s the fun in that? And even then, there are no guarantees.

Weirdly enough, over the past 5 years of travel (oftentimes in sketchy areas), I’ve rarely felt like my personal safety was threatened. But I worry about my electronics almost every day.

Staying healthy in foreign countries

Nobody ever plans to get injured or sick while traveling, but it happens. Trust me.

Yes, accidents can happen at home too. But in many countries, the relaxed safety standards and lack of education make everything riskier.

I don’t want to scare you. In fact, odds are you’ll be perfectly fine. But if you do decide to take your business on the road, don’t leave home without a good digital nomad insurance plan

Without one, all it takes is one sip of bad water, one reckless taxi driver, or one piece of malfunctioning equipment to cause a health (and financial) disaster.

Frustrating tech problems

Finding internet while traveling is the crux of my existence. When traveling, everyone wants destinations that:

  1. Are stunningly beautiful
  2. Aren’t overcrowded with people
  3. Have good internet connection

I hate to break it to you, but in reality, you will usually only get two of the three.

If you want a beautiful place to yourself, there’s likely not going to be internet.

Since the world closed down due to COVID, my wife and I are currently “van life-ing” through the U.S. Every day, we pass up amazing camp spots because there is no signal.

It may seem like a small price to pay for location freedom (and it is, I guess), but being forced to stay connected will drive you crazy. There’s no question about it.

And it’s not only internet. When tech fails abroad, it can be a pain to replace. My wife’s Macbook kicked the can in Thailand, and we had to travel across the country to replace it. It costed several hundred dollars more than it would’ve back home, and we still ended up with a Thai character keyboard.

The Pros

Now that we’ve got the bad stuff out of the way, here is why running a business while traveling is awesome.

Travel is your “motivational carrot”

You may think that constantly traveling to exotic destinations would kill your motivation for work. But actually, the opposite is true.

Once you get a taste of location freedom, you’ll never want to give it up. It pushes you to work even harder. It also forces you to become more productive, laser in on the most important tasks, and avoid wasting time at all costs.

Back home, you might let a project drag on all day. But when you’re in Mexico and have a scuba diving trip scheduled for 1pm, odds are you’ll finish that project by 1pm.

Changes in scenery are also great for inspiration. It keeps your mind fresh with a constraint stream of new inputs and ideas.

Your flexibility allows for the ultimate travel experience

When you take a “normal” two-week vacation, you rush from attraction to attraction, trying to cram as much as possible into your itinerary.

You don’t have time to smell the roses or immerse yourself in the culture.

And if you happen to get bad weather, you’re screwed.

All of these problems vanish when you take your work on the road. 

There is no rush. You can stay at each destination as long as you like. You can try all the different restaurants and spend time hanging out with the locals. And if you get a spell of bad weather, you can just wait it out.

It can make building your business easier

It can be tough to support yourself during the early stages of building a business. You may be forced to work exhausting hours just to make ends meet while you get your company off the ground.

As a digital nomad, this stage is way easier. All you have to do is base yourself in a country with a low cost of living, and all your financial stresses vanish.

When your bills are cut in half, that means you can:

  • Support yourself in half the amount of time
  • Charge less than your competitors who have a higher cost of living
  • Have extra money left over to reinvest in your business

This is exactly what I did when starting my freelance writing business in Colombia. I even had time left over to take salsa dancing classes every day. If I would’ve been living in the U.S., I never would have made it.

You get to follow your dreams before you get old and creaky

Many people dream of traveling the world as soon as they retire. The problem is that when you retire, you don’t have many “healthy and active” years left (if you have any left at all).

By taking your work on the road, you’ll be able to backpack Patagonia, bungee jump in South Africa, or run with the bulls in Spain…all while you’re still a young ball of energy. 

The truth is, life is fragile and our days are numbered. We can’t wait until “someday” to follow our dreams. By then, it may be too late.

If you long to see the world, here’s the sign you’ve waiting for! 

Whether you need to hire assistants, move your business online, or start something completely new—do whatever you need to do to make it happen.

The time to start planning is now! Before you know it, COVID will be a thing of the past and we will be able to follow our dreams (and travel plans) once again!

You definitely won’t regret it.

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