6 Mistakes Traveling Business Owners Should Never Make

With the rise of remote work—both as an employee and as an entrepreneur—it’s totally possible to own a business while spending most of your time traveling. But it can be easy to make mistakes and let things slip through the cracks when you’re juggling travel with work. You don’t want to dive into an enviable lifestyle as digital nomad just to have it cut short because of a slip-up!

Let’s look at a few of those common mistakes that entrepreneurial nomads make so that you can avoid them and enjoy your success.

1. Ignoring or Being Unaware of Local Laws

Meeting legal requirements isn’t something you want to do lackadaisically. Beyond getting your passport and visa squared away, there can be additional requirements for business owners traveling across borders, and ignoring those can land you in hot water legally and financially. This is really important if you’re going to spend longer than a vacation in a particular destination—for example, if you plan to apply for a digital nomad visa, there will almost certainly be requirements to meet for your business, like reporting income and type of work. Do your research, get your documents squared away—like your application for a FEIN number if you haven’t completed one yet—and cross your Ts and dot your Is so you don’t get in trouble, even unintentionally.

2. Relying on Free Wifi

Free wifi is super helpful when you’re out and about, especially if you’re navigating on the fly or posting and catching up on social media—but an unsecured network can leave you open to malware and data hacks.

Pick up a local SIM card (or an eSIM if your phone doesn’t use a physical card) as well as a portable wifi hotspot for those times you either don’t totally trust the networks available to you, or when you don’t have connectivity at all. This will be incredibly handy if you have a meeting, a deadline, or if you just feel more comfortable being quickly reachable by your team, customers, and vendors.

3. Not Packing What You Need

Photo by Vlada Karpovich on Pexels

Whether you’re hitting the road long-term or if you’re flying out to a conference or business meeting, you want to make sure that you bring only what you need, and exactly what you need. If you find yourself traveling for business fairly often, consider creating a packing list that you can use over and over (try one of these templates to get started) so that you don’t have to put too much thought into the essentials over time.

Read our guide to downsizing your packing

4. Forgetting Time Zones

As an entrepreneurial nomad, you might work wildly different hours than your team, customers, and others you’re in touch with regularly. It can be embarrassing to miss a call because you calculated time zones improperly—and if you do it often enough, it can be a costly mistake. One easy fix: install a world clock app on your phone so that you have a quick, handy reference for the local time in as many different destinations as you need.

And if you travel often across different time zones, you’re going to run into jet lag issues, which can be a major productivity killer. Fortunately we’ve written a whole article about what causes jet lag, how to make sure it doesn’t affect you too badly, and what to do to get your schedule on track when you’re traveling across multiple time zones.

5. Foregoing Travel Health Insurance

Your local insurance very likely doesn’t cover injuries or illnesses while you’re abroad, and things can get very bad (and very expensive), very quickly, if you get hurt or fall sick on your trip. If you’re applying for a digital nomad visa or any other type of long-stay visa, you’ll likely need to prove that you have travel health insurance to cover the duration of your stay—but this is also very important if you’re taking a shorter vacation or otherwise not required to prove you have insurance. Fortunately there are quite a few travel health insurance providers to choose from so that you can purchase the plan that makes the most sense for your trip.

6. Keeping Disorganized Records

You can’t grow and scale a successful business if you have a habit of losing receipts, keeping sloppy records, and generally being disorganized and lazy. Expense reports aren’t fun to create, but they’re necessary when you’re on the road as a business owner. Keeping a meticulous record of your business expenses—not just shoving receipts into your bag and forgetting what they’re for when they resurface later—will save you headaches over the long-term. Consider using an app to track your spending in real-time, or sit down for an hour each month to go over your expenses and note which were for personal use and which were business purchases (and what specifically they relate to, such as office supplies, meals, accommodation, etc.). Your accountant will send you a thank-you card.

Being a traveling business owner is an adventure—full of opportunities! But beware of those common pitfalls. Putting some simple systems in place before you embark on your journey will make a major difference in productivity, and ensure that you’re successful and can grow your company to match your vision.

Good luck and happy travels!

About the Author

Heather is a freelance writer who loves exploring the intersection of travel and history. Read her other articles on Frayed Passport here.

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