How I’m Using Shoeboxed to Travel the World

Rebekah Voss is using Shoeboxed to track her expenses and do her taxes from the other side of the globe. Here’s her story about how to travel the world using Shoeboxed.

I’m sitting in an open-air café overlooking the river in Siem Reap, Cambodia. This has become my office for the month, since the option to use air conditioning at my hotbox of a hotel room costs more than the room itself.

The restaurant staff gathers around my laptop in stoic silence. Everyone holds their breath as I click the “send” button. An email rushes through the ether, journeying some 7,000 miles around the globe to land in my accountant’s inbox.

I have officially finished my taxes.

A cheer goes up from the staff, and we celebrate the happy event with pitcher (after pitcher) of Angkor beer (hey, when it’s 100+ degrees at night and the beer costs $1/pint, what else are you gonna do?)

I completed my taxes from the other side of the world without making a single phone call to my tax guy, and without a single moment of stress. How did I do it?

With Shoeboxed, that’s how.

Rebekah VossWhen I left the U.S. in November of 2013, I never imagined I’d become a digital nomad, writing and working from 16 different cities (and counting) in just five months’ time.

The world has truly become my office, and as I travel, there are only three things I need to keep my business going: a sense of humor, a strong WiFi signal, and my Shoeboxed account.

Because I’m running a business abroad but still paying taxes back home, I’m able to claim just about everything – from the cost of hotels to airfare – as a business deduction.

I’d never be able to do this without the Shoeboxed app on my phone, especially because in Asia, almost every transaction is completed in cash. I get handwritten receipts most of the time, which I immediately scan and send to my Shoeboxed account.

In the past, I’ve relied on bank statements to figure out what I’ve spent and when, but that technique doesn’t work when you’re paying in Nepalese rupees!

When it came time to do my taxes, Shoeboxed was a total life saver.

At first I was a little nervous, because I’ve always relied heavily on the Magic Envelope – I love throwing everything into the envelope and not thinking about it again until I check my account and see it’s been magically updated. It’s sort of like Shoeboxed rewards you for being lazy, which I can totally get behind.

Rebekah with hat_Vietnam_editedBut in places like Nepal and Cambodia, the mail system isn’t exactly what you’d call reliable. If I mailed a Magic Envelope full of receipts and bank statements, they might arrive, they might not. And I’d rather not play dice when it comes to my finances, y’know?

Without Shoeboxed, I would’ve had no way to give my accountant access to all of my documents in such a fast, secure way.

Since I’ve been traveling the world with Shoeboxed in my corner, I’ve launched a new travel website and published my first book.

I’m confident that I’ll continue to be able to grow my business from the other side of the planet using the Shoeboxed app to scan my receipts.

And even though I have to scan my receipts myself, I actually still carry a Magic Envelope in my backpack, sort like a good luck charm.  So far, it seems to be working.

linkedin pictureRebekah Voss is a narrative travel writer and the creator of, an inspiration website for solo female travelers.  She is also the author of 175 Ways to Travel Today: How to make you dream of world travel a reality right now.

Tax Considerations for Digital Nomads and Off-Shore Entrepreneurs

Even if you’re working and living abroad, making money from clients back home means you still have to answer to Uncle Sam. In fact, depending on what country you’re in, you may still have to pay taxes to the IRS even if you’re getting paid in a foreign currency! Here are our top tax considerations for digital nomads.

Forget business travel – more and more entrepreneurs are becoming permanent digital nomads, living and working anywhere and everywhere they want (or wherever they can find a strong WiFi signal).

It’s no wonder this is such a growing trend. The benefits of being “location independent” are extensive: making money while seeing the world, enjoying a low-cost of living while still getting paid in your home currency, and creating a mobile office wherever the heck you want.

But what happens at tax time? Even if you’re working and living abroad, making money from clients back home means you still have to answer to Uncle Sam. In fact, depending on what country you’re in, you may still have to pay taxes to the IRS even if you’re getting paid in a foreign currency!

Here are our top tax considerations for digital pioneers:

1. Figure out the rules

Teaching English in Saudi Arabia is different than tutoring in Paris, at least where Uncle Sam is concerned. Your tax responsibilities will vary depending on where you are in the world and what you’re doing there.

If you’re making money in U.S. dollars, have a U.S. bank account and are getting paid by U.S clients, you’ll definitely need to pay taxes. If you’re a U.S. citizen getting paid in foreign dollars by a foreign government, you may or may not owe the IRS a percentage of your earnings. Keep in mind that you may also need to pay taxes to the government of the country in which you’re working!

Talk to your tax professional, or read what Uncle Sam has to say by clicking here.

2. Track your spending

If you’re traveling while working, or traveling for work, you may be able to write off a lot of expenses you wouldn’t normally be able to at home.

For instance, a travel blogger traipsing around Southeast Asia may be able to write off meals, accommodation and even entertainment costs as travel expenses.

The IRS is interested in knowing where your “official” home base is; i.e., the physical location of the place you do business. If that place is constantly changing, you may do well to keep a permanent residence back home while continuing to travel the globe.

Be sure to snap photos of your receipts and upload them to your Shoeboxed account for easy processing while abroad. Since many countries around the world deal primarily in cash, getting a record of the transaction is more important than ever. Have the vendor hand write you a receipt if need be, then beam it to your Shoeboxed account and assign it an appropriate category.

3. Digitize the tax process

Being location independent makes going digital more than a luxury – it’s an absolute necessity! You’re not going to be able to mail paper receipts and tax documents to your accountant from the middle of Nepal, so the entire tax process needs to happen online.

By creating one-click reports within your Shoeboxed account, you’ll be able to give your tax professional everything they need to finish your taxes swiftly and accurately.

Accuracy is crucial when filing from abroad. While the IRS now offers direct deposit in lieu of paper checks, much of their correspondence still happens through hard copies. If there is a mistake on your return, such as an inaccurate bank account number, the IRS will try to mail you a check instead. A check you won’t get if you’re in working from Siberia!

4. Digitize your mail

Speaking of the perils of snail mail, why not digitize that too while you’re at it? Earth Class Mail is a service that will receive mail on your behalf, open it for you, scan it, and post it to a secure online account.

With Earth Class Mail, you’ll never have to wonder what mail you’re missing back home – you’ll have instant online access as it’s delivered (even from 7,000 miles away).

Are you a digital nomad? How do you manage your taxes from abroad?

Essential Apps for Your Summer Road Trip

Before World War III breaks out in Rhonda the Honda, check out these eight free road trip apps that we promise will make your car ride more enjoyable (or as enjoyable as a family vacation can be).

Nothing ruins the anticipation of an exciting summer vacation like road trip misery.  We’ve all been there: you have grand ideas about how driving to your destination is going to help you save money, as well as bond with the fam.  Cue vision of laughing family playing car games and enjoying each other’s company.

However, 20 minutes into your eight-hour trip you realize that this is not going to be the case.  The kids are already whining that they’re hungry and bored, the driver is distracted from the commotion in the back seat, and you feel a massive headache coming on.  Before World War III breaks out in Rhonda the Honda, check out these eight free road trip apps that we promise will make your car ride more enjoyable (or as enjoyable as a family vacation can be).

1.  RoadNinja

road-ninja“Where’s the next rest area? I can’t wait!”

“I’m hungry!  I want Wendy’s!”

Quell the complaining with the RoadNinja app.  This lifesaver lets you know exactly what is coming up in exits right off of the interstate you’re traveling.  So when your kid needs to go right now or he refuses to eat any fast food except Wendy’s chicken nuggets, you’ll know you only have to listen to the crying for five more miles.

2.  HotelsByMe

You thought you were going to drive through the night, but you literally can’t take one more second in the car.  HotelsByMe lets you find hotels in your vicinity, including ratings from TripAdvisor, prices and real-time availability.  Get some shuteye at a hand-picked hotel for the night and start again fresh in the morning.

3.  RoadTrippers

Mashable called RoadTrippers the “only app you’ll need for the Great American Road Trip,” and we believe them.  A self-proclaimed mix of Mapquest and Yelp, RoadTrippers finds the most adventurous route available to get you to your destination.  Spice up the route you’ve taken a million times in search of something more exciting.

4.  OpenTable

open-table_thumbCar snacks are exciting for the first couple of hours, but after your three-year-old sticks the second Cheeto up his nose, they start to lose some appeal.    With OpenTable, you can read menus, check prices and ratings, and make a reservation at participating restaurants.

5.  BatteryGuru

Whether you forgot your charger at the last hotel or five people are fighting over one car charger, BatteryGuru will help save your battery life with smart changes to energy expense.  In the first few days, the guru learns how you interact with your smartphone and then comes up with a battery optimization plan based on your specific usage.

6.  Sky Map

starzAdd a night of camping under the stars to your road trip and this cosmic app will definitely come in handy.  You can search constellations as you see them with Sky Map’s GPS information about the stars in your location.


7.  Postagram

Screen Shot 2013-06-25 at 2.48.30 PMWith this free app, you can send digital postcards of your trip to friends and family anywhere in the U.S. for $.99.  Use photos from your camera roll, Instagram or Facebook and add your own personalized message!

8.  Shoeboxed

The Shoeboxed Receipt and Mileage Tracker for iOS and Android is a great travel companion for your road trip (which can’t always been said for everyone else in your car).  You can track your mileage and route with the click of a button (okay, two buttons – “Start Trip” and “Stop Trip”).   The app also allows you to snap pictures of your trip receipts and upload them directly to your Shoeboxed account.

All of these apps sound like a great excuse to take a vacation to us!  Which of these apps sounds the most useful to you?

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