Dealing with Paperwork on the Road

Dealing with paperwork on the road can be a real challenge for the long-term traveler. Our system isn’t perfect, but it’s working out pretty well.

paperwork horizontal

One of the most problematic issues for long-term travelers can be dealing with paperwork on the road. When we had a home office, it was easy to lapse into a pattern of printing statements, receipts, emails and documents and transferring them into files. We had a nice big lateral file cabinet with lots of space to fill, other file drawers in our desks, table top trays, notebooks, you name it.

When we moved to Kaua’i, quite a bit of paperwork came with us: an expandable file of the previous year’s receipts for income tax preparation, research materials and writing references for the blog, file folders, binders and other supplies. One of the first things we purchased was a wifi printer, and we didn’t really modify our mainland ways of dealing with paperwork that much.

As road-trippers, we’d carried a portable printer, so we never really even considered any sort of paperless system. Remember when all the fortune tellers were predicting we’d be dealing with paperwork by eliminating it completely? Yeah, never happened.

The big challenge came when we decided to travel full time. Lugging around lots of paperwork is a drag when you’re limited to what you can carry. There is definitely no room and no desire to carry portable printer and blank paper. While we can make use of hotel business centers and the kindness of the homeowners we house sit for, we’ve still implemented additional cutbacks in paperwork. And I have to say, I really like it.

The photo below is what dealing with paperwork on the road now looks like for us.

dealing with paperwork

Our little office paperwork and file system

There’s an expandable file of last year’s records which will be sent back to storage in the mainland U.S. after our 2014 taxes are done. A couple of flexible poly notebooks are fitted out with pocketed dividers and page protectors: 1) travel documents organized in sections by destination, and 2) PassingThru-related notes and references organized by topics: business plan, post topics, social media, email, podcasts, technical and other. The zipper case with the post office design holds our passports, international drivers licenses, a couple of thumb drives, USB cords and a notepad. The external hard drive relieves the MacBook Air’s limited memory (and allows for digital hoarding, if truth be told). If I need to take a meeting, I use a zippered legal pad case in which the Air and the iPad both fit, along with business cards, pen, calculator, etc.

dealing with paperwork

Old school to-do list because I like the act of crossing things off as done with colored Flair pens

The big change for 2015 will be using Shoeboxed (use that link and get a discount) for receipts. You take a photo of the paper receipt with your phone and upload it into the app where it is categorized by real humans. 🙂 Other features include gmail sync, business card scanning, and if you must and we won’t, envelopes you can fill and send into them for processing. Dealing with paperwork on the road just got streamlined to the max. Before, I was carrying around paper receipts from each location. Shoeboxed has eliminated the need for that and now we can just toss them.

For the few pieces of paper mail we still receive, we’re using St. Brendan’s Isle mailing service. Dealing with paperwork the SBI way couldn’t be easier. They give us a physical address, receive it on our behalf, scan the outside of each piece of mail and we have the choice of having them open it to scan the contents, hold it, or discard. Once we’ve seen the scan, if we need them to process further, such as mail a check in to our bank for deposit, we just email the instructions. Couldn’t be easier!


The travel doc notebook

We’re just getting the hang of putting travel docs on our phones, and I’ll admit I’m still more comfortable with old school printed itineraries, check-ins and boarding passes. Perhaps putting them on both the iPad and the iPhone would reduce the possibility of a screw-up. There was one instance where Pete’s boarding pass on his phone scanned correctly, and mine didn’t. Fortunately, I had a backup printed out. I’m not sure what would have happened without it.

In any event, my personal technology and the two notebooks fit nicely in my briefcase carry-on. The larger expandable file, extra cords, adapters, a few office supplies, business cards and other tech accessories fit in a wheeled leather carry-on we call “The Office.” This is organized with a variety of plastic containers and scavenged pouches to try and keep things tidy and accessible.

dealing with paperwork

Once the blue expandable file goes, this case will be less of a burden

Here are a few of the specific items (click image for details, Amazon affiliate links) that get high marks for durability, as well as being fun to use:

What methods do you use for dealing with paperwork on the road? Please share in the comments. We’re always looking for better ways to be organized!

And just for fun, below are some items Amazon thinks are relevant to this discussion. If you click through from here and make a purchase, we’ll earn a small commission. Thanks!


    • Betsy Wuebker says

      Hi Antonina – It didn’t take long for us, but it helped having a deadline. The trip was going to begin, so we were compelled. 🙂

  1. says

    Hi Betsy,
    We are one of the last generations to even understand the term “lateral file cabinet” — and thank goodness. I commend you on your journey into paperless!
    My journey there will be more difficult because of the crutch called my condo. The fact that I still have that lateral file right behind me now in my home office keeps me tethered to that system. And I don’t have to lug the ten-ton thing around with me, so there’s no impetus to dispose of the thing or the system!
    Thanks for sharing your story of progress!
    Josie has an awesome blog post here: Free Airfare 101My Profile

    • Betsy Wuebker says

      Hi Josie – Thanks for giving me the heads up that you’d commented. I honestly think that we’d still have that lateral file cabinet thing going without our “drastic” move to Hawaii. It took a big shakeup like that to jolt us out of our paper habit, and even then it didn’t work completely until we went nomad.

  2. says

    You’ve got a great system going there. I scan everything, including work contracts, etc. If Rev Canada ever comes knocking I need proof that I have been out of country all these years. Also, I have discovered that getting a passport renewed from another country is much easier if you have all the paperwork and info. at hand. I have a file listing all of my past addresses, and people who I can rely on for references and guarantors, and also past employers with will all pertinent dates. I store everything on my computer and in my dropbox.
    Nancie has an awesome blog post here: Bangkok: Taste of Thailand Food Tours for Travel Photo ThursdayMy Profile

    • Betsy Wuebker says

      Hi Nancie – Good idea on the file with all your past data. We didn’t make use of our scanner as much as we could have when we had one. I think I’ll be far more conscious not to lapse if we ever revert to a base location again.

  3. says

    I found this very interesting. You are very organized. I guess traveling light necessitates that. I am not a full time traveler, but spending 5 months away from home requires some method for dealing with paperwork as well. An expandable file folder is my friend.
    Donna Janke has an awesome blog post here: Ancient Heart of PhoenixMy Profile

    • Betsy Wuebker says

      Hi Donna – Yes, I was very proud when I reduced our years into one expandable file each a while back – we were dealing with a LOT more paper before that. Now we think the expandable file is a space hog , so we’re trying to dispense with it. (I do have an empty one just in case).

    • Betsy Wuebker says

      Hi Billie – I started my personal conversion when we downsized to move to Hawaii. And even then, we shipped more paperwork out there from the mainland than we should have. Ridiculous, not to mention the expense. Now I’m a real zealot. 🙂

    • Betsy Wuebker says

      Hi Tom – This was born out of not wanting to burden our daughter, who graciously accepted responsibility for our tiny storage unit in MN, any further. Pete is advocating getting rid of even that. Just in case we didn’t have something to fight about, I guess. 😀

  4. says

    Thanks for these great tips. Since I don’t travel full-time, I’m still a dinosaur, printing everything out. You’d think just the cost of printer cartridges in Mexico would have cured me of that. I ordered my first smartphone on Cyber Monday and wil be picking it up when I visit family in the US in a couple of weeks. I also wo a year of the Trip-It Pro app. I’m hoping that will make a difference. After my last 5-week trip, I am on a crusade to rid my luggage of every possible ounce. for my upcoming 7-weeks the road.
    Donna meyer has an awesome blog post here: POTW: Amsterdam’s Magere Brug, the Skinny BridgeMy Profile

    • Betsy Wuebker says

      Hi Donna – I forgot to mention TripIt. I got Pete a subscription for Christmas. I’m not too sure how it works, but he seems to like it. You’re right about how every ounce matters when you’re schlepping. 🙂

  5. says

    Well thought out and streamlined – I’m impressed!
    We, too, have learned to download our boarding passes on more than one device since all too often one of the passes won’t show…usually on the iPhone rather than my android, for some reason. Paper is a mind-easing backup for something as important as a boarding pass, but we usually do without.
    Happy travels-
    Anne has an awesome blog post here: Olives and Jazz in OrvietoMy Profile

    • Betsy Wuebker says

      Hi Anne – I’m going to try it on the iPad this time. If it doesn’t work, then I’ll be officially phobic. 🙂

    • Betsy Wuebker says

      Hi Michele – Thanks! I think I’ll do a followup after a few months and see how we feel then.

  6. says

    Funny, apart from a paper notebook (obviously to take notes), a folder for vehicle and border documents, and a small plastic sleeve for receipts we hardly carry any paperwork with us. Receipt slips for credit cards we keep until we have checked the online bill. That’s it. And we travel in a camper truck!
    Everything else is send straight to our niece who holds a “power of attorney” for both of us. If anything is important she just emails us a scan (no paper). We have a number of special directories on our harddisks to keep things in order, but that’s about it. If people want a copy of something I send them an electronic file, most papers we receive I usually photograph and then destroy the paper copy.
    If an airline asks me for a self-printed boarding pass I show them a copy on my tablet and ask them if they really expect me to travel with a printer in my luggage.
    Juergen | has an awesome blog post here: Living Fossils at Nahuelbuta National ParkMy Profile

    • Betsy Wuebker says

      Hi Juergen – It certainly is becoming more easy to reduce paperwork, isn’t it? I read somewhere that the US Internal Revenue Service wants to see actual receipts, rather than just a CC statement. So scanning or photographing is the way we’ll be doing that.

    • Betsy Wuebker says

      Hi Gypsynesters – The proof will be in the pudding, I suppose. We’re still pretty new at this full time travel gig. 🙂

  7. says

    Great tips and I love your organization – How well I remember the predictions of a “paperless future!” We’re also on the road full-time and have pretty much achieved the paperless goal by using our camera to take photos of receipts (especially medical), business cards, printed brochures with good info, etc. and then uploading them to DropBox where we organize them into files. My sister (we call her our guardian angel!) handles what little bit of mail we still receive and scans anything important. We also gave her power-of-attorney so that she could handle the sale of our house as well as access our safe deposit box. Our accountant files our taxes and all other financial dealings are online. E-tickets for airlines were our final stumbling block as printers and faxes are few and far between in Central & South America. This summer I (finally) figured out how to send them to our tablets and, since we usually have a couple of suitcases to check in we have our boarding passes printed out at the same time. However, the first thing I’ll buy when we settle down in the (hopefully far future!) is a printer/scanner!
    Anita @ No Particular Place To Go has an awesome blog post here: The Unconquerable Castle on the Hill: Castillo San Felipe de Barajas in CartagenaMy Profile

    • Betsy Wuebker says

      Hi Anita – yeah, the checking luggage thing and getting your boarding pass at the same time is the way we’ve done it up until now, too. When we were roadtripping, we did have a nice little portable printer, and I looked into one of those little handheld scanners, too. I’m hoping not to add more tech, though, while we’re in full time travel mode.

  8. says

    My wife loves to make lists; I can’t seem to manage it, relying instead on my digital calendar. We don’t travel full time so there’s always that big pile of mail and paperwork to be handled when I get back home. I do need to get organized!

    • Betsy Wuebker says

      Hi Denis – When we maintained a home base the load of mail to go through upon return was monumental! I sure don’t miss it!

    • Betsy Wuebker says

      Hi Patti – Let us know how it goes and if you discover some other ideas we could all use! 🙂

    • Betsy Wuebker says

      Hi Suzanne – You’re in the perfect position right now while you’re “rightsizing” to make some interesting changes! Let us know what you discover. 🙂

  9. says

    I am impressed!!! I feel organized, but nowhere near as organized as you. What valuable advice not only for full time travelers, but for every travel writing professional!!

    • Betsy Wuebker says

      Hi Alison – it’s funny how satisfying the simplest thing can be, like crossing off a list in a certain way. Evernote is great, but it doesn’t have that dimension.

  10. says

    We are also traveling full-time though only in the US and Mexico (so far). We carry very little paperwork with us, mostly just vet certificates and records for our dog. For our own, it’s mostly all stored on our computers as digital copies. We do have a safe back at my mother’s house where we store some paperwork we don’t need while traveling but may need at some time in the future. We also use SBI as our mail-forwarding service and agree with you — it couldn’t be easier or better for our needs. When we are out of the country, we have mail sent to my step-father, who is able to scan it in for us. Otherwise, if we’re traveling in the US and staying somewhere long enough to receive mail, we have it sent to wherever we are. It has worked fine for us so far!

    • Betsy Wuebker says

      Hi Emily – We have a package en route from SBI in Florida to here where we are staying in Darwin. It has yet to arrive, so fingers crossed. If we were only traveling in the U.S., things would be a little easier, but it’s still not bad. When we were traveling with our little dog before she passed away, her medical records and proof of vaccinations came with us, too. Hope you’re having a wonderful time!