Episode 1 24 min August 6, 2026

01: The Trip That Almost Didn’t Happen

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Some trips begin with a carefully planned itinerary.

This one began with a gate change, a dead phone battery, and the slow realization that our rental car reservation existed everywhere except the rental car counter.

In this episode, Ric Wayland and Jennifer Do revisit a trip that started badly, got stranger by the hour, and eventually became one of those stories that improves every time it is told.

In this episode

We talk about:

  • the airport delay that set everything in motion
  • how one small booking mistake became a much larger problem
  • the rental car that did not inspire confidence
  • the wrong turn that led somewhere unexpectedly worthwhile
  • what we would do differently next time
  • why difficult trips often become the most memorable ones

A few things we learned

Always screenshot the reservation confirmation before leaving home.

Never assume the last rental car in the lot is the one you reserved.

A place does not need to be famous to become the best part of a trip.

And when someone says, “This road probably reconnects with the highway,” ask to see the map.

Places and resources mentioned

  • Example hotel or destination
  • Example restaurant
  • Example roadside attraction
  • Example travel app
  • Example airline or booking service

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Photo gallery

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Transcript

Ric: At what point did you realize the reservation was not actually in their system?

Jennifer: Somewhere between the third confirmation number and the employee asking whether I was sure I had booked the correct city.

Ric: Which was not a confidence-building question.

Jennifer: No. Especially because we were standing in the correct city.

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Have you ever had a trip go wrong before it really started?

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