“My past does not define me. I am a man.”

The man himself

“I am a man” are words that Jason takes pride in saying. For Jason, the meaning of being a man is being able to provide for his family; not only their needs but, also, their wants. Therefore, the words “I am a man” are not words that Jason takes lightly. There was a time period when Jason was unable to provide. He was sentenced to 40 years for possession of cocaine and intent to distribute cocaine. Some of his years were suspended. Jason served 5 years, but his past does not define the man that he is today. Statistics show that up to 63-75% of people that have been incarcerated will go back to jail within five years. https://www.nbcnews.com/news/us-news/76-released-inmates-arrested-again-within-5-years-report-n86826. Jason Westmoreland would not become one of these statistics.

The baby of the family

Jason said that his mother always made sure that he and his siblings needs were always met. Jason’s appetite of “wanting more” led him to a different lifestyle. Jason saw finer and fancier things, and he desired them for himself. Instead of working for those things, Jason took the path of selling drugs. “Selling drugs was was the only way that I thought I could I make sufficient amount of money to suppress my appetite,” but it didn’t last long. After 5-6 year of living the lifestyle he desired, Jason was arrested for possession of cocaine, intent to sell, and distribution of cocaine. Jason served 5 years.

A picture of Jason while he was incarcerated

After serving his time, Jason tried working working 9-5 jobs. He even tried work factory jobs, but none of those jobs were for him. He still had a taste for finer things in life, but he wanted to do it a legal way. With limited education, his choices were few that would allow him to make close to the money he had gotten accustomed to making.He was familiar with trucking because his grandfather, uncles, and some cousins were drivers. Jason decided he wanted to make a career in transportation. He said rain, sleet, or snow, you’ll find him behind the wheel of an 18 wheeler. Each time he is behind that wheel, Amber, his wife, is praying for his safety.

Amber, the queen of the house

Just because there is money in the industry, Jason and Amber have made sacrifices for their family for the betterment for their family. Initially, when Jason began to drive trucks, he had to do extremely long hauls on the road. He would be gone for a month or more and would only have two days off. He knew it was a sacrifice that he had to make to gain experience. After a period of time, Jason tried the short haul. He was coming home each day. Of course with the shorter distance, the money wasn’t the same. He and Amber had a discussion. In order for him to provide the lifestyle he desired and what he wanted to be able to give his wife and children{ (Jqwon(16), Gavin(12), and Jaceion (5)} all their needs and their wants, they decided for Jason to go back to long haul. Amber said that she would much rather have Jason on the road and absent during the week versus being prison walls.

The Westmoreland family

I asked Jason what was the hardest thing being on the road. His response was not being there to help his wife. He feels that he puts a burden on her by being on the road. She has to take the kids to their football games, karate, work, and do household chores alone. Jason said on the other aspect if he wasn’t on the road that he’d be at the house looking at them, and what good would that do them? He and Amber understand that sacrifices have to be made with him being in transportation, but it is a sacrifice that they are willing to make together. With the love, communication, and commitment, the Westmorelands are making it work.

My next question to him was what keeps you motivated to drive. One of the benefits is seeing the world for free. Jason said that he is paid to travel the US. He gets to see beautiful sceneries, mountains, and things he might not have ever seen before had he not been a truck driver.

One of the greatest benefits of driving is that Jason loves the fact that he can provide for his family. “It is a blessing not living paycheck to paycheck. I don’t have any worries when it comes to financial stabilities. I wish I’d started driving 20 years ago. I could have been a millionaire and retired by now.” By being in transportation, it has provided him the opportunity to purchase a new home for his family. Amber was desiring a new vehicle. A few Saturdays ago, he left the home with intentions of going to grab a sausage and biscuit. Instead, he came home with two new vehicles for their family. When his kids say “daddy I want this”, Jason said he has to stop himself from buying everything at that moment. Some of the reasoning for going ahead and purchasing what the kids wants is because it is his way of making sure that his sons do not go down the path that he was once on. He encourages and pushes education to them. If they decide on a trade, Jason will encourage them to do that as well. He knows that the 9-5 jobs aren’t for everyone. His oldest son told me that he might become a truck driver whenever he graduates. As we all know, truck drivers make the world go round.

The Westmoreland family

I asked Jason what advice would he give to anyone that is considering driving trucks. He would let anyone know that their are other options besides selling drugs. He said that a career can be made in driving trucks. “You have to leave home freely. If you don’t, you will leave home forcefully, be in a situation that you regret. It is great money, but sacrifices have to be made.” We discussed sacrifices earlier, but one of his sacrifices he made was that he moved away from home. The Westmorelands lived in Nashville for approximately 6 months. It didn’t last long. Jason said “I am a momma’s boy.” The family moved back to Mississippi. He doesn’t criticize the next person because he was once there. That way for him was simply turned into another direction (positive).

Jason now drives for Milan Supply Chain Solutions

If you are looking for Jason Westmoreland, you won’t find him behind a prison wall. Instead, you can look out your window on the highway, you might see him in passing on the highway in his 18 wheeler.

It won’t matter if it’s rain, sleet, or snow, you can count on Jason to be behind the wheel of his 18 wheeler being the man for his family. Be safe driver. You are appreciated.

This is Jason’s truck. He’d gotten stuck in the yard the night before. He was waiting on a tow truck to come pull him out. We got a laugh out of it.

**Here’s the link if you want to see the full interview. https://youtu.be/2_87O94_5Jk

Published by Carman

I am a banker by day, but writing and photography have always been my passion. Writing is therapeutic for me. It gives me peace.

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