The habits that keep trucking businesses alive

Sure, anyone can buy a truck. But successfully running a trucking business, day in and day out, through market highs and sustained lows—that's an entirely different challenge.

Deb LaBree is the founder and trucking coach of A Woman Trucker and an owner-operator herself. In today's newsletter, she shares the clear signs that a trucking business will succeed in the long haul (pun intended) and why she learned early on to never get too comfortable. 

—Interview by Shefali Kapadia, edited by Bianca Prieto

What do you think is the hardest part of growing and maintaining a trucking business in today’s market? 

Freight volatility paired with rising equipment and operating costs are the biggest challenge right now. Rates shift quickly, and trucks, trailers, maintenance and insurance are more expensive than ever. The real difficulty isn’t just navigating a downturn—it’s having the discipline during strong markets to prepare for one. Trucking runs in cycles. I’ve seen many owner-operators expand too quickly when cash is flowing, only to struggle when rates soften.

It takes maturity not to chase shiny things when money is in your pocket. Sustainable growth requires cash reserves, conservative decision-making and long-term thinking. Stability in this industry comes from discipline, not momentum.

From your personal experience as an owner-operator, what’s one big lesson you learned that you’ll never forget?

Never get too comfortable. Early in our business, we secured dedicated freight, and it created stability. For a few years, we didn’t have to watch the load board or monitor market rates closely. Then one day, we were notified that another carrier had underbid the lanes and the contracts were gone. I wasn’t actively tracking alternative freight opportunities, and we had to pivot quickly.

That experience taught me that no lane, no contract and no customer is guaranteed. Even when business feels steady, you must stay aware of the broader market. Monitor trends. Build relationships. Keep options open. Security in trucking doesn’t come from a single contract—it comes from staying engaged and prepared.

What advice would you offer to someone starting a trucking company or building their fleet?

Find a successful mentor in the area you want to grow into. Learn from people who have already walked through both the strong years and the tough ones. Ask questions. Listen closely. Pay attention to how they handled challenges, not just how they talk about success. Trucking has highs and lows, and experience shortens the learning curve.

No one builds a sustainable business alone. Surrounding yourself with seasoned operators who are willing to share honest insight can help you avoid costly mistakes and build something that lasts.

What’s the No. 1 indicator to you that someone starting a trucking business will be successful?

Coachability and long-term thinking. The individuals who succeed aren’t just asking how to get loads—they’re asking how to build a sustainable business. They seek advice from experienced operators, study financial fundamentals, and apply what they learn in a way that fits their own model.

Anyone can buy a truck and run freight. Some are very good at it. But growth requires more than movement—it requires planning for change, managing cash flow and understanding margins.

The most successful new owner-operators are willing to learn, adjust and make disciplined decisions early. They treat trucking as a business from day one, not just a driving job with a higher payment attached.

What challenges do women still face in the trucking industry?

While the industry has made significant progress, perception can still be a challenge. I’ve experienced situations where I introduce myself clearly as the owner and driver, yet the conversation shifts to, “Tell the driver…”—not realizing they’re already speaking to one. It’s not always intentional. Often it’s a habit or assumption. But it highlights that visibility and representation still matter.

Progress is happening. More women are entering ownership and leadership roles. Continued visibility, competence and collaboration will keep moving the industry forward.

What can the industry do to better support and attract more women into trucking?

Support starts with practical decisions, not slogans. Safety is the top concern for most women entering this industry. That means providing well-maintained, reliable equipment and addressing repair issues promptly. When drivers feel physically secure in their trucks, everything else improves.

Representation also shows up in small but meaningful ways. If uniforms are provided, offering proper women’s sizing matters. Professionalism includes ensuring that women are equipped to do the job without feeling like an afterthought.

Flexibility around scheduling and home-life balance is another factor. Many women manage family responsibilities alongside their careers, and creative operational solutions can make a difference. At its core, support comes down to respect, safety and thoughtful policies. When those are in place, recruitment takes care of itself.

Thanks for reading today's edition! You can reach the newsletter team at editor@theinsidelane.co. We enjoy hearing from you.

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The Inside Lane is curated and written by Shefali Kapadia and edited by Bianca Prieto.