A New Road Ahead: Scholarship Helps Former IT Pro Train for a Truck Driving Career

For nearly three decades, Madison Harper built a career in information technology. As a client success manager, he helped businesses maintain relationships, solve problems, and keep their systems running smoothly. It was steady work for 27 years, but changes within the industry led to his layoff last fall.

Since then, Madison has faced repeated rounds of job interviews in the field, often making it to the final stages before being passed over.

“I’ve made it to the fifth and sixth round of interviews multiple times, and then not getting picked,” Madison said. “The market is just flooded right now.”

After watching the IT hiring landscape shrink and teams being dramatically reduced in size, Madison began to see the writing on the wall. It was time for a career change, but in which direction? What skill could he learn today that would still be valuable tomorrow, no matter what happened in the tech world?

His answer? Hauling freight.

Now training at Sage in San Antonio, Madison was recently named the recipient of a $1,000 Howes Truckers of Tomorrow Scholarship. This financial boost will help him as he builds a new professional foundation—one that trades home offices and virtual meetings for nighttime highways and 18 wheels.

A Skill That Travels Across Industries

Madison didn’t arrive at trucking out of desperation. He approached it the same way he would evaluate a business strategy or a client roadmap. He researched industries that consistently need workers, even during economic downturns.

“Freight is one of those industries,” he said. “There’s always going to be demand.”

There was also a personal connection. Since childhood, Madison has been fascinated by large trucks and the idea of the open road. That early curiosity resurfaced as he considered practical options for his new career.

“My goal was to get a skill that transcends whatever industry I’m in,” he said. “If I have a CDL, I always have the potential for a job.”

Madison approached selecting a school with the same diligence. He researched multiple CDL programs throughout the San Antonio area, from large institutions to smaller local options. What ultimately drew him to Sage was its administrative team.

“Summer Ferguson did a phenomenal job answering my questions,” Madison said of his Sage a
admissions representative. “She was personal, and I wasn’t just a number.”

He also valued the school’s industry reputation and the sense that instructors and staff were invested in student outcomes beyond graduation. “But mainly it was the people,” he said. “That’s what stood out the most to me.”

From Scholarship to Career Training

Madison came across the Howes Truckers of Tomorrow Scholarship while he researched different truck driving schools in the San Antonio area. He read stories about past recipients, and seeing others—especially those who, like him, were changing careers—helped him believe the opportunity might be worth pursuing. Still, he remained cautiously optimistic.

“I honestly didn’t think I was going to get it,” he said. “Scholarships usually go to younger people, not someone my age.”

So, when he received the call saying he’d been selected for the $1,000 award, he felt both surprise and gratitude.

“I was shocked. Honored,” Madison said. “I’ve been on unemployment since October, so every dollar matters.”

“We are proud to recognize Madison as a recipient of the Howes Truckers of Tomorrow Scholarship,” said Rob Howes II, President of Howes Products. “His excitement and commitment to pursuing a career in trucking embodies the very spirit of this program and we look forward to seeing him succeed as part of the next generation of trucking professionals.”

Beyond financial support, the scholarship served as validation that starting over was the right choice. His experience so far at Sage has also helped put his career anxieties at ease. Three weeks into training, Madison has already completed his first driving sessions and says the learning curve feels manageable. While he had some experience around trucks and trailers, handling a full tractor-trailer is entirely new territory.

“I’m picking it up pretty quickly,” he said. “Though I didn’t have the experience, I knew I could do it.”

He credits much of his confidence to driving instructors Kenny McElveen, Ervin Shearer, Jeff Trigg, and Rick Lopez, who he says focus on the mechanics of driving as well as the reasoning behind each maneuver.

“They’re patient,” Madison said. “They don’t just tell you what to do. They explain the how and the why. And when you mess up, they teach you how to work your way out of it.”

Starting Over with Confidence

Madison expects the first few years of his trucking career to involve long stretches on the road while building experience. Over the long term, he’s interested in becoming an owner-operator and potentially starting his own company, perhaps one that specializes in tanker hauling or heavy transport.

“The more technical, the better,” he said.

In the meantime, he feels comfortable embracing his new path despite having been forced to reconsider his future.

“This wasn’t the plan,” Madison said. “But you have to be flexible. Stuff happens. The question is how you react. At the end of the day, I’m getting a skill I can leverage for years to come, and that makes starting over okay.”