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.
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.
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.
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!
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.
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!