This is the third article in a series about The Birthday Project. You can read part two here.

As we walked along the back of the lines waiting at the Southwest Airlines ticket booths, looking for the right clerk, I knew that there was a real possibility that the plan might not work. Only a week earlier I had pitched my birthday idea to my friend a Kevin. Now we were in Orlando, actually getting ready to do it.

The plan was to let the airline clerks at airports across the country choose the destinations of our one-week U.S. tour. We would simply present our credit cards to the ticket sales clerks, and ask them to choose. City to city. Around the country we would go. Travel Roulette, if you will. I had talked a friend of mine named Kevin (it didn’t take much arm-twisting) into joining me, and here we were.

Southwest was the largest carrier at the Orlando airport, and Kevin chose a young lady clerk, because we thought she might tolerate the proposal, all being recorded on video, mind you. We knew that if we chose the wrong clerk we could end up explaining our plan to the TSA all afternoon, rather than flying out.

Kevin chose the first clerk well. Mandy was her name. As soon as we explained that we wanted her to choose the first destination on our trip, charge our credit cards, and give us tickets without telling us where we were going, she agreed. I was shocked that it had worked. In the back of my mind, I’m not sure I really thought we could pull it off.

But she was into it. Mandy began scouring the computer screen for the right destination. The only constraint we gave her was that we needed to stay in the U.S. We only had a week. And we knew multiple one-way tickets would add up fast. This wasn’t a world tour. Just the U.S.. Other than that limitation, it was completely up to her.

Having heard the excitement over what we were doing, as she chose our first destination, other ticket clerks came over to see where she was sending us. They all seemed to agree it was a good choice.

Soon she had charged our credit cards, printed the tickets, and was explaining that she loved food. I love food too. This was sounding promising. If your going to be in the south, she explained, you’ve got to have bar-b-que. “Sounds awesome to me, I thought. “I love bar-b-que.”

Dallas, Texas it was.

At first I was a little surprised she chose Dallas. All week long I had imagined the different places we might end up. My thinking was that it would be a major city. When you ask people to name a fun place to visit, big cities come to mind. I just knew that it would be New York, or San Fransisco, or Vegas. A major destination. But now that I look back, we told her it was our first stop on a one-week adventure. It makes sense that she only took us to the first step. I always wanted to go to Dallas, but had never been. So I was excited about her choice.

It was about this point that I let Kevin in on a little secret. I was afraid to fly.

My whole life I had only been on three planes, and one of those trips was as a child. A flight I didn’t remember. The other two included a flight from Gainesville, Florida to Miami to interview with a law firm, right after law school. And the third flight was to Chicago about 15 years ago to launch a magazine that I founded. Neither of those flights could be avoided.

Over the years, I had often avoided flying by driving. I loved to take road trips, and managed to drive wherever I needed to go for work, fairly easily. And, as a family, we had traveled every inch of the eastern seaboard. Always by car. But in recent years it had become apparent that if I and my family were going to see the world, I would have to get past my fear of flying. For my 50th birthday I wanted to take some risks. Do something that scared me. This trip was, at least in part, to put that fear behind me once and for all. It was time to open up the world.

Kevin was not amused when I explained to him that I had a fear of flying. But I assured him I would be fine. We got some lunch and waited for our flight which was scheduled to board in about two hours. It had been a long, fast-paced week. This was the first opportunity I had to relax since pitching the idea to Kevin the week before.

We sat at the Macaroni Grill restaurant in the Orlando terminal completely beside ourselves. It had worked. The clerk chose our destination. And we were almost on our way. There was a sense of success in the air. We had no idea what we had gotten ourselves into.

Our that day flight left Orlando in the late afternoon. We were off to Dallas. Having not been on a plane for fifteen years, I was nervous. I recorded everything. The people, the seats, the window. It was a whole new world.

Part 4 of the story is coming soon.