Driver Spotlight: How Will Kling Brings Old School Values into the Modern Era of Truck Driving

Driver Spotlight: How Will Kling Brings Old School Values into the Modern Era of Truck Driving

A legacy driver’s journey into the industry

When you ask most people when they got their start in their career, their answer will typically involve when they studied in college or that job in their 20s that set them on their path. Will Kling’s story goes a little bit differently, though.

Kling (aka Lil Dawg) began his career as a truck driver when he was 8 years old. Yes. 8. He didn’t realize it at the time, of course, but qualities of respect and appreciation for the truck driver were instilled in him by his grandfather, William, who also gave him his name. It is that respect and appreciation that would serve him greatly in his adult life and eventually lead him to follow the same career path.

In the passenger seat

From the age of 8 until 14, Kling spent just about every summer riding in his grandfather’s truck all over the Northeast—and not just as a passive passenger.

He would carry his own little briefcase to match his grandfather’s and even kept his own logbook. “While my grandfather was working in his logbook, I was coloring in mine.” These summers spent on the road would come in handy many years later when Kling felt unsure of what to do with his life.

Before we get to that, though, it’s important to understand that Kling is a veteran. He joined the Navy at the age of 17 on a waiver. While many of us were making all of our dumb teenage decisions, Kling was already serving his country. After serving for six years in Aviation Ordnance, Kling re-entered civilian life and began that difficult transition from military to civilian life.

“There’s nothing in the real world that compares to your life in the military. You can’t go get a job at Walmart detonating bombs. There’s just nothing like that. It’s hard to fit back in.”

The difficult road back to civilian life

That struggle sent Kling on quite a journey to find where he belonged in the civilian world. He spent years trying out a number of jobs and career paths.

He got his GED, worked in the concrete and steel industries, ended up on unemployment for a time when the steel company shut down, started his own business, went back to college to study criminal justice, learned software development, worked in marketing and advertising, and got a job at a sheriff’s office.

Despite all that effort, though, Kling could not escape a feeling of monotony and a sense that he did not belong.

This brings us to that moment when those summers with his grandfather come in handy. While thinking on what his next move should be in his search for contentment, he found himself reminiscing about those times on the open road, and it suddenly made sense. He should drive a truck. He realized that truck driving could give him as a sense of independence and freedom that an office job couldn’t, so he decided to get his CDL.

He was able to qualify for a veteran’s program that would pay for his training, and with that, he was back on the road just like when he was a young boy. Without the briefcase, of course. Technology has changed quite a bit since those days with his grandfather.

Giving truck drivers an online community

In fact, technology now plays a significant role in Kling’s life as a driver as the creator of his own Youtube channel, Lil Dawg.

When asked why he decided to start a YouTube channel in the first place, he responded, “I saw another guy doing it, and I knew I could do better.” That display of confidence has carried him far.

His channel receives 350,000 to 400,000 views per month. It seems that those post-military years of wandering and picking up video marketing skills served him well.

He may have started his channel because he knew he could do it better, but he continues for a new reason. Growing up in the industry, he has seen the camaraderie among drivers dissipate. He wants to reinvigorate this sense of community among drivers and believes that by answering questions and giving viewers a look at what it’s really like to work as a driver, he can help other drivers feel less alone. In this way, he uses modern technology to help revive the old-school values that he got to experience with his grandfather.

His online presence has also helped raise awareness of scam companies who are taking advantage of drivers and has even helped raise money for a driver who fell on hard times while working for one of these companies. “I see now that I can really make a difference with my videos,” Will says.

More to be done for drivers

Beyond YouTube videos, Kling believes that much more can and should be done by us all to improve a driver’s life.

“People need to remember that everything you touch, eat or wear at one point was on the back of a truck, and a person had to work hard to get it to you.”

He wants more public awareness around the issues faced by drivers so that they can get the help they need and the respect they deserve that they used to see years ago. “Truck drivers used to receive a lot of respect as professional drivers. Right now, though, they are underpaid, overworked, and unappreciated.”

Despite the hardships faced by drivers, he appreciates the life it provides for him and his family. Now that he’s in the driver’s seat, he brings his four daughters along on the road in the summer—just like his grandfather did when he was a kid.

He’s continuing the legacy of instilling hard work and an appreciation for the industry that serves us all.

Be sure to read a story that Will’s wife, Becky, wrote—from the wife’s point of view: The Top 4 Lessons I Learned on My First Overnight Trip on My Husband’s Truck.


Katlyn Whittenburg

This story was written by Katlyn Whittenburg (@katlynisit), who is a technology writer specializing in logistics and transportation. She accidentally discovered her love for logistics after working for a startup. Katlyn strives to make the industry that drives our economy as interesting to everyday people as it is to her.

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