Tell us about the worst trip you ever took.

One of the best trips that I have ever been on also contained the worst motel experience I have ever encountered. The year was 2008, and my divorce had been final for a little more than a month. I went in to work one day and decided that I needed some time off, so I scheduled vacation for the following week. I didn’t know what I was going to do or where I was going to go, but I knew I wanted to get out for a few days.

I’m not sure how it all came about, but I decided to go to Chicago. I had been to Chicago one other time in the summer of 2001 for a Pampered Chef convention when I was a consultant. I spent a few days in the Windy City being bused back and forth between the hotel and the convention center, but I never saw anything beyond the bus and hotel windows. My mom thought it was a terrible idea for me to go on this trip alone (despite me telling her that after my divorce, I just wanted to be free), so she made my brother go with me. In hindsight, it was a good idea, but you know how that goes.

We made several stops to and from Chicago and made a huge trip out of it that included Louisville, Dayton, Sikeston and Martin, but I’ll talk about those another time because those were the good parts. We’re here to talk about the worst part, right?

I made no/zero/zilch/nada reservations for this trip. I was going to be FREE, remember? We drove into Chicago in the evening, and headed toward the O’Hare area. My dad had suggested that we stay in that area and to avoid the Cicero/Midway area like the plague because he said it wasn’t the safest area in town.

I also knew I wanted to stay in an area near the train so that we wouldn’t have to drive into Chicago for tourist stuff and sightseeing, so we ended up in the Rosemont area. If you’re not familiar with the area (and I’m still not), there’s a convention center nearby that apparently drew in billions of people to the area who booked up all of the rooms in the nearby hotels.

What happened next? Read Part II of the story!

Have you ever been faced the possibility of having nowhere to stay when going out of town? 

Has your life been shaped by a mentor or have you been a mentor to someone else? Tell me about your experiences!