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Family tradition: Love for trucking, family drives Tyler Woolley to excellence

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Family tradition: Love for trucking, family drives Tyler Woolley to excellence
Illinois driver Tyler Woolley is a third-generation trucker, following in the footsteps of his father and grandfather. (Courtesy: Tyler Woolley)

An honest living doing something he loves — that’s how Tyler Woolley describes his trucking career. Working from Wyanet, a community on the famous Hennepin Canal in north central Illinois, Woolley hauls eggs and other temperature-controlled products for Arteberry Transportation.

Tyler Woolley's Rig
Trucker Tyler Woolley takes pride in keeping his bright red 2016 Peterbilt Model 389 glider sparkling clean. The rig is paired with a Great Dane temperature-controlled trailer. (Courtesy: Tyler Woolley)

Woolley’s bright red 2016 Peterbilt Model 389 glider, which is teamed with a matching 53-foot chrome refrigerated trailer, is featured on the Arteberry website. The truck features an extended frame, a 20-inch chrome bumper and stainless battery boxes, and Hogebuilt half fenders. The Great Dane trailer features a Carrier refrigeration unit, spread axles and — as Woolley’s 2-year old daughter Ray likes to point out — a “shiny hiney” (chrome cargo doors).

“It’s not overdone; it’s not underdone,” Woolley said. “It’s practical to get to everything and easy to keep clean.”

Keeping his truck clean could be seen as an obsession on Woolley’s part.

“That’s something I pride myself on, is being clean all the time, even in the winter,” he said. “Sometimes I check the mail before my wife does, so I can get the bank statements (and) she doesn’t see how many times I get (the rig) washed. I might get a wash four times a week if I run in the rain or the salt on the road.

“I mean, I don’t know but it’s just an image,” he said of his desire to make the truck look its best.

Like many drivers, Woolley’s trucking career started at an early age.

“I was a baby, riding around in trucks with my dad and grandpa,” he said. “If I was given a project at school, I’d write about trucks or make truck projects in art class. I was always ‘that’ kid.”

As a teen, Woolley began to live his dream.

“When I turned 18, my dad took me to get my CDL and I started hauling,” he said. “I was still in high school.”

Woolley’s grandfather farmed and drove trucks, so much of his early trucking experience was agricultural, hauling either grain or livestock. There was flatbed work, too, before moving on to asphalt and hauling “hot rock” for a local company.

Soon after that, he discovered temperature-controlled trucking.

“I started pulling for Del Monte in Mendota, Illinois. That’s where I got my feet wet in the reefer deal,” he said. “We used to run from Mendota down to Dallas quite a bit and just keep on turning them. I fell in love with it, and that’s all I want to do now, to be honest.”

Woolley joined Arteberry seven years ago and says he loves what he does.

“I haul a lot of eggs for the Amish communities down in Missouri and in Colorado,” he said. “There’s a lot of LTL (less-than-truckload) stuff, little mom-and-pop drops — and of course I get the big warehouses and Walmarts, too.”

Some drivers don’t care for the amount of freight handling refrigerated loads can require, but it’s no problem for Woolley.

“I like getting out of the truck for a minute, breaking it down,” he said. “I go to the same places, do the same stuff. So, it’s kind of like you’re on personal levels with everybody at the places you deliver.”

Relating to customers on a personal level is a great perk of the job, according to Woolley.

“I love working with the Amish on the eggs,” he said. “I mean, they’re like family now. We talk on the phone, send text messages back and forth, and I get invited to weddings and all that. They’re like family now.”

Tyler Woolley and Family
When he’s not on the road, Tyler Woolley treasures time spent with his family, which includes wife Breanna, son Brayden (far left), daughter Rae and the family’s newest addition, 1-year-old son Rowan. (Courtesy: Tyler Woolley)

Wooley’s wife, Breanna, comes from a trucking background; her father and several of her uncles are drivers. Her relatives, however, drive mostly local or regional routes that bring them home every night, so adapting to Woolley’s over-the-road schedule presented a challenge.

“I tell her this is not a ‘nine-to-five’ job,” he explained. “I don’t come home every night. It’s not just a job — it’s a lifestyle.”

Eventually, she adapted to Woolley’s work schedule, and now she often helps clean and polish the truck.

“She’ll try to get me going every once in a while,” he said. “She sees a picture of a truck and tells me, ‘You should do this’ or ‘Why don’t you do that?’ That’s a pretty easy thing to answer since I like to keep the expenses down.”

The couple’s son Brayden, who soon turns 12, is already showing signs of inheriting his dad’s interest in trucking.

“He can drive it down the road,” Woolley said. “I don’t even have to shift gears for him — and I’m trying to teach him to back in now. With a long truck and a 53-foot trailer, it can be intimidating.”

Brayden frequently rides along with his dad in the summer months when school is out, and he has his own favorite customers, Woolley said.

“They’ll send him shirts or hats in the mail, and he’s even got to do way cooler stuff than I’ve gotten to. One guy took him out in a crane, just for the experience,” he said.

Woolley has no plans to change his job or his life any time soon.

“This is this is what I plan to do,” he said. “There’s nothing else I could ever picture myself doing. I always tell people I wouldn’t trade my worst day trucking for their best day at their nine-to-five.”

When he’s not trucking, polishing his truck or talking to friends about trucking over a couple of beers, Woolley enjoys camping with his family, which includes the newest addition, 1-year old son Rowan.

“My wife’s family has a cabin up in Eagle River, Wisconsin, and we have a makeshift campground right outside of the town where we live,” he said. “We’ll get eight or 10 campers in there and have a good weekend.”

Woolley is also proud that his children — especially his oldest — are taking an interest in trucking.

“I kind of know what my grandpa and my dad felt like watching me do that kind of stuff,” he said. “I tell them to never just scrape by, but give it their best.”

The trucking industry may be very different by the time the next generation of Woolleys is ready to take the wheel — but there’s a good chance they’ll do it with the pride and determination taught to them by their father.

Cliff Abbott

Cliff Abbott is an experienced commercial vehicle driver and owner-operator who still holds a CDL in his home state of Alabama. In nearly 40 years in trucking, he’s been an instructor and trainer and has managed safety and recruiting operations for several carriers. Having never lost his love of the road, Cliff has written a book and hundreds of songs and has been writing for The Trucker for more than a decade.

Avatar for Cliff Abbott
Cliff Abbott is an experienced commercial vehicle driver and owner-operator who still holds a CDL in his home state of Alabama. In nearly 40 years in trucking, he’s been an instructor and trainer and has managed safety and recruiting operations for several carriers. Having never lost his love of the road, Cliff has written a book and hundreds of songs and has been writing for The Trucker for more than a decade.
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