When the Day Job Calls: Our Mad Dash From Northern Michigan to Chicago

This happened during Fourth of July week in summer 2026, while we were parked in Frankfort, Michigan, on our Oshkosh or Bust RV road trip.

Full-time RV life and a full-time job usually get along just fine. Then there are days like this one.

We were parked in Frankfort, Michigan, driving a dented truck with a taped-up headlight after a run-in with a deer. Safe to drive, said the body shop. Just not pretty. Remember that part.

The Dinner That Kept Moving

Stefan had a client dinner in Chicago on the calendar. Originally, it was planned for our week in Michigan City, Indiana, an easy hop into the city. Then it got pushed. And pushed again.

By Wednesday, with Friday a federal holiday, Stefan sat down for lunch and announced, “Well, guess it’s not happening this week. Who would want to meet for dinner ahead of a long weekend?”

The Slack message came in right after that. Dinner. Chicago. Thursday, 6 p.m. Tomorrow.

We were now about five and a half hours away.

Plan A: Fly

Chicago isn’t a long flight, so Stefan did a quick search for the nearest direct flights out of the regional airports. Booked out. It was Fourth of July week, after all.

Plan B: Rent a Car

The plan was easy. Mack and I would spend the afternoon exploring Traverse City and drop Stefan off at the rental car counter on the way. He’d take his time driving to Chicago, park, catch up on email and still have a comfy safety buffer. He was already dressed for dinner. He had a reservation from a booking site, confirmation in hand. What could go wrong?

At the counter: “Hey, sorry man, we don’t actually have a car available. Somebody should have called you.” They hadn’t.

A confirmation in hand, it turns out, is not the same as a car on the lot.

Plan C: The Dented Truck (and Me)

So with no other options left, I drove. The dinner was in Evanston, just north of Chicago, and we didn’t want to risk Stefan circling for parking at 5:55 in a huge truck. City parking is not easy with an F-350 long bed. And with five-plus hours each way and a dinner running until 10 p.m., driving himself home that night wasn’t a safe option anyway.

First, though, we had to take Mack home, about an hour’s detour. Leaving the dog alone overnight wasn’t an option, so Mack offered to stay home with the dog herself. (She was great with the dog, and perfectly happy on her own.) I grabbed a few things for an overnight hotel stay while we were there.

And just like that, the safety buffer was gone. The ETA, in non-rush-hour traffic, said 5:50 p.m.

Racing the Clock

Traffic was mostly fine. What really got us were the cash toll booths. When we hit the toll booth backup, we looked at each other and thought, well, that’s it. It’s over.

Then came Chicago at rush hour. We watched the ETA and the clock like hawks, and the ETA did not care about our feelings. It now showed 5:57. We prayed we’d make it without a total standstill, navigated through the city and finally arrived.

I dropped Stefan off a block away from the restaurant. Nobody needs their client watching them climb out of a dented F-350 with a taped-on headlight. Just in case.

Dinner was at 6:00. Stefan walked in at 5:59. The client walked in at 6:02.

The client never found out Stefan had driven in from northern Michigan that afternoon just for that meeting. It never came up, and there was no reason to tell. Cool, calm and collected. Nothing to see here.

Meanwhile, Back at the Hotel

While Stefan was charming his client, I checked into the hotel, then made a run to Trader Joe’s to stock up on goodies before heading back into the “wilderness.” Then I took a long hotel shower. After a day like that, nothing beats it.

3 a.m.: It’s Raining. Inside.

I woke up first, then Stefan. Still half asleep, we both scooted over to get away from the wet spot. Then, slowly, the obvious question: why is it wet?

Eyes open. Loud dripping. Feet on the carpet: squish. Stefan stumbled over his briefcase. Me: “I moved it over there. It was a dry spot… sorry.”

The ceiling looked like Swiss cheese, and it was dripping, aggressively, all over the room. The carpet was soaked. The mattress was soaked. We were, at the very least, damp. A big storm had rolled in overnight and dumped a lot of rain in a very short time, and that rain was now finding its way through the holes in the ceiling and into our hotel room.

We’d planned to leave early anyway, so we packed up and checked out. The night clerk looked barely interested. Stefan tried again: “Hey, I don’t want to raise a fuss, we wanted to leave early anyway. But you should really have someone check it out.” Blank stare. “Like, the mattress is soaked. The floor is soaked. It is really raining inside. It’s wet. WET.” It finally seemed to register.

That got us a quick but heartfelt apology. To the hotel’s credit (a well-known chain we won’t name), they called us after someone checked out the room, apologized and comped the room, then called again afterward to apologize one more time.

The Hum of the Open Road

The drive home was not a magical sunrise-over-Lake-Michigan moment. It was gas station coffee and tired silence. We just wanted to get home.

Then the truck started to hum. About 300 miles of, let’s call it, “spirited” highway driving had frayed the tape holding the broken headlight together, and the loose end had caught the wind. Our F-350 now came with its own soundtrack.

So at a gas station somewhere across the Illinois-Indiana border, we filled up and re-taped the headlight. Glamorous, this business travel life.

We rolled back into the campground tired, a little damp and very ready for a nap. But you know what? We still had a good time. Some of our favorite stories come from the days nothing goes to plan.

What We Learned About Business Travel From the Road

• Build in buffer. Then build in more. Three minutes makes a great story. It is not a great plan.
• A reservation is not a car. Especially through a third-party booking site on a holiday week. Call the counter and confirm there’s actually a car on the lot.
• Regional airports fill up fast around holidays. If there’s any chance you’ll need to fly, look early.
• Know your tolls. Cash toll booths can eat your buffer in a hurry.
• Someone has to hold down the fort. When your house is on wheels, the pets don’t come with you to the client dinner. Thank you, Mack.
• Keep good tape in the truck. You never know.

This post is part of our stories about mixing full-time RV life with a job that still needs you in person every so often. Find more on our Life on the Road page, including The Travel-Free Week That Wasn’t.

Have you had a road-warrior scramble like this? Tell us about it in the comments!