When most drivers enter the trucking industry, they start out behind the wheel for a company. This provides a stable income, benefits, and a chance to gain valuable experience without the heavy financial responsibility of owning a truck. After a few years on the road, many drivers begin to wonder if it’s worth going out on their own as an owner-operator.

We spoke with seasoned professional drivers who have logged years in both roles to weigh the pros and cons.

Pros of Being an Owner-Operator

One of the biggest draws to becoming an owner-operator is the income potential. Depending on how specialized the freight is, an owner operator can make three to four times the annual income of a company driver.

For Jeremy and Tiffany Wallin, a husband-and-wife trucking team, this was a major motivator. The Wallins shared, “For us, it’s all about long-term financial goals and the desire to retire early while still maintaining financial security.”

Beyond the paycheck, being an owner-operator allows you to build equity in your truck and create a business that fits your lifestyle. For financially disciplined drivers, having a strong emergency and maintenance fund provides a safety net for when breakdowns occur. With proper planning, the highs of independence can outweigh the risks.

Cons of Being an Owner-Operator

Higher earnings come with trade-offs. As an owner-operator, you lose out on company benefits like health insurance, paid vacation, and coverage for truck maintenance and fuel. Every expense comes out of your pocket.

You’re not just a truck driver - you’re a business owner. That means handling paperwork, taxes, compliance, and maintenance schedules is all your responsibility. Many underestimate how much time and effort go into managing the business side of trucking.

As drivers Jim and Kellie Doyle put it, “When you drive for a company, they decide where you go and when, but you carry zero financial risk or liability.”

Freedom and Control

The biggest benefit of becoming an owner-operator is the freedom and control it brings. You decide what load to take, what routes to run, and when you go home.

Jeremy Wallin described his journey:

“I was introduced to trucking when I was five years old, riding with my dad in a ’77 International Transtar cabover. By the time I was 21, I had my CDL, but in less than six months of driving for a company, I realized it wasn’t for me. I didn’t like not having any say in my life. That’s when I met an older owner-operator who became my mentor in trucking. He sold me my first truck, a 1984 Peterbilt 362 Cabover. I immediately took it and had it painted Candy Apple red at my cousin's paint shop for free. I found a company to lease onto out of Scottsboro, AL. From there, I learned the business firsthand. I’ve had successes and failures, but I never fell out of love with being an owner-operator, and I always will be until my last mile. Everyone’s path is different. Give it 3-5 years to learn the business and research the niche you want to be in. Become an expert, then you can be successful.”

Advice Before Making the Jump

Not every driver is ready to dive into being a business owner right away. Veteran driver Jenn Kohl offers this advice:

“Everyone is different, but I’ve always maintained that anyone who wants to be an owner-operator should spend at least five years as a company driver to learn the industry. I also suggest that before you make the jump, pretend to run your company truck as an owner-operator and track all your expenses. If you can be profitable on paper, and that includes a fair salary for yourself, then you might make it. I also suggest saving money, building credit, and buying or leasing your truck from a company unrelated to the carrier you plan to sign on with.”

Jeremy Wallin summed it up well: “Everyone is different. Some people have resources, some don’t. But if you’re passionate, willing to learn the business, and prepared to handle challenges, being an owner-operator can be one of the most rewarding paths in trucking.”