Steven Greig: From Second Chances to Teaching the Next Generation

After growing up in Toronto and spending decades working in family-run construction and heavy equipment businesses, everything changed when Steven’s company closed. What was once steady work turned into uncertainty. His family relocated to the Kawarthas, and suddenly, after more than 20 years in the workforce, he found himself without a job and without a high school diploma.

“I never worked for anyone else,” he says. “I didn’t even know how to make a resume.”

One day, driving past the Adult Education Centre in Lindsay, something clicked. Encouraged by his partner, he decided to walk in and ask a simple question: Could I finish high school?

Returning to school later in life was intimidating. He enrolled full-time, committing from September to June, while balancing family responsibilities and raising a young daughter.

“It was nerve-wracking,” he recalls. “I was older than the teacher.”

After finishing high school, he visited the Vocational & Career Counselling Services (VCCS) for help building a resume. During that meeting, a counsellor asked him a question that would change his life:

“Do you want to go to college?”

“It had never crossed my mind,” he says.

With guidance from VCCS, he applied for funding through Better Jobs Ontario and was accepted into Fleming’s Heavy Equipment Operator (HEO) program.

Although he had years of experience operating heavy equipment on job sites, the HEO program filled in critical gaps he’d never had the chance to learn.

“I’d run machines my whole life, but no one ever explained how they worked,” he explains. “Now I understood the mechanics, the maintenance, the safety, and the why, not just the how.”

The hands-on learning, supportive instructors, and real-world training transformed his confidence. Instructors stood out not just for their expertise, but for their calm, patient approach. They helped students realize that complex machines were manageable and that learning was possible.

“It wasn’t as out of reach as I thought,” he says. “That was huge.”

Steven then went from student to faculty, almost overnight.

After graduating, he began looking for work when something unexpected happened. An instructor reached out and encouraged him to apply for a teaching position at Fleming.

“At first, I ignored it,” he admits. “I thought there was no way I’d ever qualify for something like that.”

When the encouragement came again, he applied. Within days, he was interviewed and hired. He started the following week.

Today, he’s back at Fleming, not as a student, but as faculty.

“I’m still in shock,” he says. “My friends didn’t believe me. My daughter didn’t believe me. I had to show them my staff card.”

His journey gives him a unique connection with students, many of whom are fresh out of high school or unsure of their next steps.

“I can read them,” he says. “I’ve been where they are, nervous, unsure, wondering if they belong.” He prepares students for the realities of the field while encouraging them to believe in themselves.

“It’s a tough industry,” he tells them honestly. “But it’s a good one. And you can do this.”

For anyone sitting in an Adult Education classroom wondering if more is possible, his message is simple:

“It wasn’t out of reach. While finishing high school at the adult learning centre, which looks directly onto Fleming’s HEO program, he would look across and think, ‘That would be cool.’ Now, here he is.”