Mechanic turned trucker Dustin shares why he left the shop for the road, chasing a better life for his family and reflecting on what people still don’t understand about truck drivers.

Jerry’s job puts him in the middle of the most dangerous road conditions imaginable, working long hours on a 24/7 standby schedule whenever storms hit. He shares stories from the highway, the accidents he’s witnessed, the reckless things drivers do in winter conditions, and the constant pressure of keeping roads safe while everyone else is trying to get home.

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Sandra reflects on what it means to be a woman in trucking for decades, the subtle comments, the assumptions, and the strength it takes to keep showing up, especially balancing a life in a family-run operation and balancing motherhood with miles on the road, later to open up about the emotional toll of selling a truck she poured years of work into, only to later learn it had been burned down, and how that loss hit harder than expected.

Jeff reflects on the old-school mentors who taught him the trade, the “last of the real cowboys” who lived through the toughest eras of trucking when communication meant pagers, payphones, and maybe a call home once a week. The feelings of being underappreciated are real, and not just by the public, but sometimes even by family, and the personal toll that decades on the road can take.

We’re honoured to welcome Shelly Walker, CEO and founder of the Women’s Trucking Federation of Canada, for a powerful conversation about life on the road and the realities of being a woman in the trucking industry. Shelly shares her firsthand experiences from years behind the wheel; from long-haul driving to navigating a male-dominated space, and opens up about the personal challenges that ultimately pushed her to build a national support network for women in blue-collar work.

Ali chats with 23-year-old trucker Jarrett, whose entire family is immersed in the industry. They dive into Jarrett's experiences as a young driver, the evolution (and decline) of trucking, family life on the road, favorite routes, pet peeves like cattle haulers, and the future of the profession—from electric trucks to autonomous vehicles. Filled with humor, controversy, and insider insights.

Matt is a truck driver in Ontario with 13 years in the industry, to talk about what trucking is really like as a career, not the fantasy version. From long haul to short haul, Matt breaks down the differences, the lifestyle shifts, and the real money side of the job.

Bir opens up about the realities he’s faced in a highly competitive industry; rate undercutting, price squeezing, and the frustration of watching wages barely move since 2014 while costs keep climbing. Bir reflects on the drive that brought so many Indians into trucking, rooted in social status, stability, and the promise of building something better, and how that promise has shifted over time.

Abraham breaks down the contrast in trucking standards, safety, fuel access, pay structures, and the everyday realities drivers face. Abraham reflects on how moving to North America reshaped his life, why many drivers here don’t realize how much opportunity and protection they have, and where the industry still falls short, especially when it comes to respect and racism on the road.

Will shares his reflections on the trucking industry as it stands today, the political climate surrounding it, and the kinds of questions drivers naturally wrestle with over time. Will also talks openly about whether he’d want his kids to follow in his footsteps.