Lessons From the Road: Herb Windl Reflects on 28 Years of Truck Driving

How do you sum up a career?

That was the question for Herb Windl, a Transport America driver who retired from the company last fall after 28 years as an over-the-road solo driver.

Herb launched his career as a professional truck driver at the ripe age of 50 years old, after he spent more than 30 years as a dairy farmer. Now, at 78, he’s looking forward to spending time with his wife, Bee, whom he married about two-and-a-half years ago, and working on his 35-acre farm near Sullivan, Wisconsin.

“The only reason I retired is because I didn’t want to miss retirement,” says Herb. “Bee is going to retire, too. She’s in the process of selling her dress alteration business in Fort Atkinson.”

By the way, Bee just turned 100-years-old and runs Berdine’s Stitchery, a small business that employs three other seamstresses.

While Herb misses his daily routine of driving for Transport America throughout the Midwest, he’s thinking about a different type of travel – visiting relatives in Texas and Arizona and just relaxing.

Back in the early 1990s, one of Herb’s two sons took over the family dairy farm and encouraged Herb to consider truck driving, which he did.

Herb started his career with a another carrier then switched to a local company, Robert Hanson Trucking, out of Darien, Wisconsin, which would eventually be purchased by Transport America.

“I went from being a driver for a company with 200 drivers to working for Transport America, which had more than 1,000 professional drivers at the time,” says Herb.

“I’ve always enjoyed driving for Transport America,” Herb adds. “They always treated me very well. And their commitment to safety is second to none. They respected me by allowing me to be the captain of my ship and to pull over when I felt driving conditions were not safe.”

It’s that dedication to safety that allowed Herb to reach his first 1 million miles driven safely in the early 2000s, and 2 million miles in 2010. He was just 40,000 miles away from earning 3 million miles when he had a minor driving incident on I-90 near Janesville.

“I hate that you have to start all over,” says Herb. “But I get it. That’s why it’s so hard to achieve.”


Lessons Learned

As he looks back at his career, Herb says there are some lessons he’s learned that he’d like to share with younger drivers, such as his sons Jeff Windl, and Andy Windl, both truck drivers.

First, realize that professional driving is a lifestyle.

“It’s a good life if you like it,” he says, “but you have to like to drive and you have to accept the fact that you’re going to be away from home.”

Second, be well organized and take your time to make sure your truck is operating well.

“I take safety really seriously,” says Herb. “Always take your time. Leave early so you don’t have to rush, and take that extra moment or two to make sure your truck and trailer are working the way they’re supposed to.”

Third, work closely with your fleet leader.

“It’s important to have good communications with your fleet leader,” he adds. “I don’t like waiting around, or not being home when I need to be. That’s why it’s important to be clear about what you need so your fleet leader can help you.”

“I enjoyed my time as a professional driver at Transport America.” said Herb. “I always appreciated their commitment to safety and they got me the miles I needed to earn a good paycheck”. “I really enjoyed that chapter of my life and am enjoying this new chapter too.