6 Boring Things I’d Rather Not Think About While I Am Traveling the World

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Travel is usually pretty exciting, but there are some boring, but necessary things to think about if you plan to travel and especially if you plan to work on the go. We try not to think about it too much, but if you’re preparing for your own trip, we hope this helps you get ready.

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Tax season is on us and even though we travel and run our businesses from cafes in Milan to backpacking in South Africa, we still need to think about our taxes. Of course, working remotely and running a blog as a business means we get to work from anywhere (literally anywhere), it also means we still need to file our annual taxes back home. It’s boring but it is necessary for us to keep up our connection to our home country.

We really don’t want the IRS coming after us when we finally do return to our hometown. I am so thankful for tax software and direct deposit so we can take care of everything remotely. I also appreciate bookkeeping software to help me track expenses throughout the year so that everything is simplified. Modern technology makes traveling and doing the boring parts of the business so much better.

Being Sick

I’ve mentioned before that I’ve been sick on the go. While medical care is much cheaper to pay out of pocket in rural and remote parts of the world, it’s also important to keep a healthcare plan in the event of anything major. No one wants to be left footing the bill for surgery or broken bones if they don’t have to.

You can easily get healthcare quotes to help you find an affordable plan that offers everything you think you’ll need. Check for things like out of country expenses, emergency transport for international trips, and more.

Travel Medical Insurance

Some people choose travel insurance over traditional healthcare plans or in addition to them. These travel medical plans are designed for short or long-term trips and can cover the costs that your insurance back home won’t touch.

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Broke a leg on a mountain and need a ride down? Travel insurance has your back. Need to go to a hospital for a few days for sickness? Travel insurance. If your home policy won’t cover international trips, that’s where this type of insurance really shines. They offer policies for trips of less than 30 days all the way up to a year or more.

Trip Interruption Insurance

Okay, there are a lot of insurances on here. The good news is that if you’re traveling the world, you don’t need to worry about car insurance if you always take public transportation.

This is the last one I promise. Trip interruption insurance protects your investment in plane tickets, hotels, and even replaces the cost of your belongings if needed. You never know when theft or faulty airline equipment can cause you major headaches. Unless you’ve ever needed to replace all your clothes in a foreign place, well, you won’t understand how valuable this insurance can be.


If you love to exercise your right to vote, then here are a couple of options and it may depend on what state you’re from. Some states will allow digital nomads to do mail-in voting if they have a domicile or home address and in some cases, even email voting. This gets a little tricky, so if you hope to still vote, you’ll want to check your home state’s voting laws to see if you’ll still qualify. 

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Another option is to plan to return home during major elections you want to vote in. Keep your driver’s license and a home address in good standing and this shouldn’t be an issue. Again, check local laws just to be sure. We try not to think too much about it. But we know politics can affect even people who travel for a living.


A lot of places don’t require special Visas if travelers only stay a short amount of time. Because we work and travel, some places require us to use a special business Visa.

It’s important to do a little research to see if the type of business you run would allow you to operate under a regular tourist Visa or under a digital nomad or business type of Visa. They also incur a cost. In some places it’s simply $10 when we arrive and in others, we need to get the Visa before we can even hop on a plane to get there.

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