Even the most seasoned travelers come across obstacles while on the road. From forgetting to schedule a payment to losing a credit card hundreds of miles away from home, there are, unfortunately, always opportunities for lessons learned.

We recently learned some very valuable money lessons — at a roadside diner of all places!

Let me explain…

The Diner Debacle

It’s day two of an eighty-day road trip. Yes, eighty. Our anticipation and excitement are so extreme we can almost feel it in the car. On the interstate in southern Illinois, quiet windmills and expansive prairie lands set the scene for an easy day of driving. When our stomachs start to rumble it’s time to stop for lunch.

We’re discussing our plans for the next few weeks, when we pull into the parking lot of a dinky restaurant attached to a gas station. We both order simple sandwiches because we know a non-greasy meal is wise before a long drive. Although the place is packed, the employees are unfazed. Two older women behind the counter bicker back and forth about who is supposed to be cleaning what. An older gentleman sitting across from them chimes in with his two cents, clearly a frequent patron. Other tables are filled with lone truck drivers and weary travelers, like us.

When it’s time to pay our bill, the particularly loud woman behind the counter walks over to the register. My husband reaches for his wallet and fumbles around, patting his back pockets, then his front. He is pulling out every card with the exception of the one he is searching for.

“Can’t we pay yet?” says one of the kids standing in line with the family behind us. “What’s taking so long?” says the other. You can tell they’ve reached their quiet-time quota.

My husband looks over to me, eyes wide, and whispers, “I can’t find my credit card.”

The server gives us a puzzled look as we step aside and let the family go ahead of us.

About a dozen thoughts flashed into my head. And none of them were good. Washing dishes, sweeping floors, operating the deep fryer, or cleaning out the back of the diner (!) were some of the dirty jobs I thought our host might ask us to complete. The place certainly needed all of them done. I imagined having to do these tasks while muscling through the humiliation, glares, snickers, and wisecracks from the diner’s peanut gallery.

After some whispering, we conclude that it must have fallen out in the car. As we walk towards the door, the server shouts in her raspy voice, “And where do you think you’re going?”

All eyes are on us.

Our faces turn bright red. I could swear even the small child propped up in her high chair dropped her noodles to give us a once over.

We exchange telepathic glares, knowing neither of us want to face the embarrassment of sticking around inside while the other leads the search for the missing card.

I lose the imaginary coin toss as my husband shrugs his shoulders and heads toward the door.

When he finally comes back, he has cash in his hands. Thankfully, the restaurant is attached to a gas station with an ATM machine.

Realizing we aren’t going to settle the bill by doing their dirty work, the surly server cracks a smile but seems disappointed that we’re going to be on our way. And that we are. Fast.

We never did find the missing card, but luckily, we had access to the information needed to both cancel and receive a new card while on the road.

Money Tips for the Road

After years on the road, we’ve learned a lot. Managing money and bills while traveling sounds like a daunting task, but there are ways to stay on top of your financial game. Here are some tips you can use whether you are going on an overnight trip or a three-month-long backpacking adventure:

Get Organized

First things first, get organized. It was a big relief when we realized we could easily get in touch with a customer service representative to help us replace the card. Remember to always have your credit card customer service phone number saved for easy access.

Get Mail on the Road

But we had another dilemma: The card was new, and we were trying to hit a certain spend to earn the sign-up bonus before it expired.

Next step was figuring out how we could get a new credit card mailed to us on the road. After some research in the parking lot, we were relieved to learn that the United States Postal Service has what they call “General Delivery.”

The free service lets you to send mail to any post office in the United States that accepts General Delivery. We sighed with relief when we discovered a location along our trip route.

Go Paperless and Sign Up for Online Banking

Choose to go paperless and sign up for online banking for all accounts. Download your bank’s mobile app, which probably allows you to deposit checks, transfer money, and pay bills on the go. Setup autopayments, if possible. This will help you stay on top of your finances no matter where you are.

Access Your Mail 24-7

If you can’t use a mail forwarding service, plan ahead by using a mail scanning service to have the outside of your envelopes and packages scanned for important mail.

Travel is a way of life for us, so we’re excited to share ways to make it as easy as possible. Take these tips and run with them, because who knows, they just might help you avoid cleaning out the back of a diner someday.


Angela Essington is the co-founder of Dang Travelers and a road tripping aficionado that just completed her goal of seeing all 50 states. Her love of travel has created an avenue for captivating readers through storytelling. Follow her adventures on Dang Travelers where she shares her experiences and tips for planning unforgettable journeys.