Freckles and I were driving down the interstate on one of our back-and-forth Mississippi to Florida excursions. We started talking about all the trucks on the interstate and what it would be like to see the country and get paid to do it. I had never even stood next to a semi, let alone see the inside of one. I remembered, during this conversation, a sales rep who sold houses with me. He decided to leave sales and drive a long haul truck with his wife. Having no idea what that even was, I asked some questions. He explained that they would be a team, both would drive. One drives, one sleeps. That way the truck never stops moving and makes more money. I told Freckles this story, and we laughed it off with a “someday” wave of the hand. The problem with an idea like that was that we had children at home, and no way we could be away from them for that long. But one day maybe when they are all grown up?

Early in 2015, Freckles worked with a man named Willie. Willie had just gone back on the road driving for an owner operator for one of the large trucking companies. His wife, Elvira, was still working with Freckles and mentioned it to her. Willie heard I might be interested and gave me the owner operator’s phone number. I called him, and he offered me a chance to pay for my school if I fulfilled a year-long contract driving for him. Very common way to get started in trucking, although I had no idea. I talked with Freckles and my (now all grown up) daughters about the idea, and they gave me their blessing. Now all I needed was courage and commitment. We saved up a bit of money, and I’m here to tell you, it’s a damn good thing because the first year is a struggle. I signed my name, scheduled my schooling, and off I went.

Jacksonville was not far from Pensacola, but it was my first taste of being away from my family and everything I had known. February 2, 2015 was the first day and the first time I had ever sat in an 18 wheeler. The first day an instructor asked me what experience I had and I said, “Five minutes ago I sat in one… does that count?”

Well, he smirked and said, “Well, you’ve towed a boat or something, huh?”

“Nope.”

He just kind of shook his head and mumbled something about “we will help.” Well, that’s all I needed: somebody to doubt me. The final piece for me to reach my full motivation, and I don’t even remember his name.

The school was just designed to get us a license. The people that truly thought they were there to learn what they needed to know to make a living driving a truck were very disappointed. The course, after all, was just 2 1/2 weeks, and the only driving was a few miles around town. I found a few like-minded people, and we formed a study group as recommended. A lot of material, and we didn’t sleep much, but we got it digested. I stayed focused and was the first to get randomly selected for final testing. I wasn’t expecting that, but I pulled up my big boy jeans and passed first try. Written test, road test, backing skills. That is a real, real, good feeling, but it was short lived. I realized that night: now I have to go out in the world and not kill people!

I spent the first month with the owner, and he was tough enough on me that I learned some extremely important skills. We also bonded and got along very well, and I will always be grateful for that start. We all have good and bad in us, and spending night and day in a truck together everyday exposes a lot. We helped other truckers and drivers often, and he was very concerned with trucker etiquette. Fuel island times, lane passing, and many more. I actually hear his voice in my head to this day, sometimes. One thing he did moved me and was unexpected. I was in the sleeper and not all the way asleep yet. I felt him sort of swerve and set the brakes. Then I could hear him talking. Next thing you know, he’s digging all around up front and cussing under his breath. I decided this was worth investigating and threw on a shirt and stuck my head out the curtain.

He said, “I’m trying to find some money, you got any change or anything?”

I just started looking and found a few dollars and handed it to him and he had found some as well. We didn’t carry much cash, it’s just not necessary usually. He immediately turns to the driver window and hands an old lady all of it. She was crying, and I found out that her kids left her there, or something, I don’t remember. But I do know that he saw her standing there crying and pulled to the shoulder, she didn’t wave him down. The amount of money we dug up was enough to get a cab home safely.

Elvira and Freckles are at home this whole time and getting restless. Things were not going well in their careers, and they wanted to be with their husbands. Well, I wasn’t surprised about Freckles because that was our plan the whole time. But the fact that she could go through the school with her long-time friend was a bonus to say the least.

Willie was not enjoying his co-driver at all, and so the stage was set. Willie and I would be a team for the month or so it would take the women to get licensed and trained. Willie planned to train his wife as he had a lot of experience. I, on the other hand, was worried about what to do because I did not. I also did not want her in a truck with a complete strange male for a month. So basically, I begged the owners ex-wife (a trainer) to make herself available, and she did. Another thing that I will eternally be grateful for.

I jumped in a truck with my friend Willie and asked him, “Has anybody ever told you that you look like Willie Nelson?”