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How to Take Long Working Road Trips

This is a photo of a sign post with 17 directional signs, symbolizing a long extended journey.

A six month road trip? It’s easier than you think.

To have a long “working” road trip vacation, read these expert tips to digitize, automate and make it easy.

The longer you stay away, the more complicated things can become. It doesn’t have to be difficult though, if you automate everything possible before you leave.

We’ve already covered road trips with pets and preparing your home for a vacation. You’ll either bring your pet, send it to grandma’s house, or make arrangements to have it lodged. You’ll also have someone come by to clear flyers and phone books from your doorstep, water the plants, cut the grass, and empty the mailbox.

All the bulk mail can go to your UPS or post box. But what about paying the bills and all the other “life stuff” that seems to come up?

One thing you can do is automate payments. That means putting everything you can on your credit card and paying it off automatically, at the end of every month. You can’t carry a balance on this particular card though, it has to be paid off every month.


First, sign into each and every one of your utility accounts. They are the monthly bills like phone, hydro, internet, medical, cellular, etc. Set them all to auto bill your cash back credit card. Then go to your bank and have the card auto paid from your checking account. Now everything gets billed to the credit card, which gets paid automatically from the bank account. Set it and forget it.

Not every utility company is on the ball though. Many government ones lag behind and you’ll still have to pay those manually. Where I live, it’s the hydro company that provides the power. I pay them $200 four or five times a year, so I don’t have to think about it every month.

Sometimes you can put your services on hold, or disconnect them while you’re gone. After all, you won’t be needing cable TV, home phone, or the internet while you’re gone.

Phone the utility and tell them about your trip. Ask about disconnect and reconnect charges, or if they have other options. It might be worth canceling, or putting certain services on hold, while you’re away. My internet company gave me a two month credit. I wouldn’t have got it if I hadn’t called them.

Check your car insurance and health insurance policies. You may be covered while out of the state or province, but only for three to six months. So if you’re planning on going away for a long time, be sure to contact them to find out what your options are.

If you want to cross any borders, check when your passport expires. It must be valid for at least six more months after arrival at customs, otherwise they might turn you back. If it does need to be renewed, start the process at least two months before your trip. 

Paying personal tax is something that everyone is familiar with. You can either avoid going on extended vacations during that time, or hire a digital savvy accountant to do most of the work for you. 

The way I do it, is to have all paperless statements sent to my email. I markup the PDF files on the computer with expense codes that my accountant gave me. When tax time comes, I zip up the PDF files and email them to my accountant.

A couple of weeks later, the tax returns are complete. All I need to do is digitally sign a copy of the return and she does the online filing. This lets me minimize the amount of time I spend on tax issues.


It’s the same deal with my corporation. (I know it sounds impressive, but anyone can own a limited liability company for tax purposes.) The accountant does the tax and its all digital.

So is company’s annual report, that I need to file through my lawyer. (Again, it sounds impressive, but it’s just a once a year formality.) It’s all digital, using PDF files and the virtual signing of documents. It just takes a little preparation.

For example, before my first long road trip, I scanned in three copies of my signature and three sets of my initials. That made it easy to copy and paste them into any documents that needed signing while I was on the road. 

These days, it is even easier to digitally sign documents. All that’s needed is the built in camera on the Mac laptop and the Preview app that comes with every Mac.

Just load the PDF document you need to sign into Preview. Sign your name on a blank piece of paper and hold it in front of camera.

Now under the Tools menu, choose Annotate, Signature, and it will photograph your signature into the document. Very cool and very handy to have when on the road.

Last but not least, is another “gotcha” especially for Canadians (your country may vary) is that you cannot stay in the USA for more than six months. If you do, you must file an American tax return, even if it’s a zero balance. And once you do file, they expect a return, every year, for the rest of your life.

So if you want to have a long road trip vacation, and get work done, it’s easier than you think. It just takes a little preparation. Automate all your bill payments. Find digital savvy accountants and lawyers familiar with PDF files and digital documents. Scan your signature into the laptop. And be sure to check your insurance coverage. If you do all that, a six month working vacation can be productive and fun.

Did you like this article? Here’s a similar one, “How to Work from Hotels on a Road Trip.” It has all sorts of tips for a successful working road trip.


QR Code for Driving Road Trips
This is the QR Code for https://drivingroadtrips.com so people can easily scan and transfer a page displayed on a laptop to their phone. It makes for easy sharing too.