Career changes can happen for all kinds of reasons — sometimes out of need, sometimes out of frustration. But for Lenell Gross, getting into the trades was about something more personal. After years of rehabbing homes on Chicago’s West Side, he saw an opportunity to take his skills in a new direction. His move into drilling, with help from HIRE360, a workforce development nonprofit, is a story of steady progress, hands-on learning, and finding the right support to take the next step.

“I’m from the West Side of Chicago, the Austin community,” Gross begins. “I’ve been interested in construction since I was a little kid, about 8 years old. My grandfather was a carpenter. He picked up the trade on his own, and I remember as a little boy going to people’s homes with him and learning the trade and how he operated the carpentry side of things.”

It’s a memory that would quietly lay the foundation for a future in skilled trades.

Years later, that early exposure to construction turned into something bigger. Gross began buying condemned properties across Chicago — homes that had been left behind or neglected for years. It wasn’t just about flipping houses for profit; it was about restoring something that had been lost.

“Going through the neighborhood and seeing houses abandoned made me want to bring value back to the community,” he says. “I wanted to show that it can be done with some hard work.”

For Gross, each rehab project was personal. He saw potential where others saw problems — and he put in the time, sweat, and effort to bring these homes back to life. In doing so, he wasn’t just improving properties; he was investing in the neighborhoods he grew up in, sending a message that these places, and the people who live there, still mattered.

But it wasn’t until recently, in his 40s, that Gross decided to shift gears.

“I wanted to do something different,” he says. “HIRE360 came across my desk, and I realized I wanted to be even more hands-on and learn a new trade.”

Gross’s story isn’t just about individual reinvention; it’s about opportunity meeting preparation. Through HIRE360, Gross discovered the world of drilling and a way to transition from general construction to highly specialized, in-demand work.

What is HIRE360? It’s a nonprofit that takes a comprehensive approach to workforce development, bringing together unions, contractors, and developers to open doors for individuals from historically underrepresented communities. With over $100 billion in upcoming construction projects in Illinois, the group is committed to ensuring that these opportunities reach the neighborhoods that need them most. HIRE360 also partners with programs like CEJA and Climate Works to expand access to pre-apprenticeships in the growing clean energy and climate-resilient construction sectors.

The organization’s “demand-driven” approach — aligning training with real job needs — sets it apart. For Gross, this model made all the difference.

“I got all of the certifications that they put in front of me,” he recalls. “And Local 150 is what interested me the most because I enjoy working with heavy equipment, and I’m certified for that.”

That enthusiasm led him to a two-week evaluation with Local 150 in Wilmington, Illinois. From there, things moved quickly: “After filling out applications, I got a call back. Then I did the drilling evaluation for two weeks in Wilmington, and here I am today — a driller helper for Local 150.”

Gross is now in a four-year apprenticeship program where each year brings new responsibilities and deeper expertise. “Currently, I’m a driller’s helper,” he explains. “I enjoy doing something called soil sampling. It’s when we go in, maybe 40–50 feet, and before they do any new construction, we will go down and test the soil and send it to the lab to test the contents and density. That has been really interesting to me.”

Gross has found not only professional growth but also joy in the work. One project stands out in his mind as especially rewarding: a large-scale dewatering operation.

“We just de-watered a project about 30 acres to put new construction on it,” he says. “We were transferring the water from underground to a new location, so we actually made a pond. It was cool to see a pond being dug and then filled with water — you could almost go fishing in it. That was very exciting to see all of that water come from underground to the surface.”

The job is physically demanding, but that’s part of what Gross enjoys. “I love getting dirty every day,” he said.

When Gross talks about HIRE360, there’s a sense that the organization provided more than just training and job placement — it gave him a new community.

“HIRE360 made me feel like I was a part of a family,” he says. “They help everyone out with whatever you need; gas, transportation, bus cards, certifications — anything — they really help you get in the door.”

He also notes how encouraging it was to see younger people going through the same program. In a world where many young people feel disconnected from traditional education or unsure of career paths, programs like HIRE360 provide a real alternative.

“Growing up, I wasn’t really good with school and didn’t want to go to college,” Gross shares. “I knew that school just wasn’t for me. For kids like that, I think it’s worth picking up a trade. It’s cheaper than school, and there are plenty of good organizations and people that will help you get set up for an apprenticeship and career.”

His advice is as practical as it is motivational: “Take advantage of apprenticeship programs. Hone in on your skills and be the best you can be.”

A Model for the Future

Gross’s story is a perfect example of how workforce development can change not only individual lives but also the trajectory of entire communities. Programs like HIRE360, which combine access to industry leaders with hands-on support, mentorship, and real job connections, are essential in addressing both workforce shortages and systemic inequalities in access to good-paying, skilled trades careers.

From fixing up abandoned homes to working on major construction sites, Lenell Gross has stayed focused on building a lasting impact. With certifications under his belt and real-world experience growing every day, he’s setting solid foundations for a new chapter in his career.

His path hasn’t been easy, but with support and a strong work ethic, he’s shown that it’s never too late to learn a new trade or take your life in a different direction.

Gross’s story is a clear reminder: change is possible, especially when you’ve got the right skills, the right support, and the drive to keep moving forward.

For anyone considering a career in the trades or looking to start their next chapter, learn more about workforce development support at HIRE360.