A 38-Year Trucking Career That Began With a Career Change in Wisconsin

When a planned business purchase fell through and factory work looked unreliable, a Wisconsin gas station dealer chose trucking as a path to steady work. He began training while still running his station, then spent 38 years driving before retiring in 2018. The change wasn’t a straight line from one secure job to another: it began with a failed sale, uncertain local employment and doubts about whether life behind the wheel would suit him.

His account is useful for what it says about how people enter trucking. A driving qualification can create another option when a small business or local job market stops looking dependable, but the credential alone can’t settle whether the work will fit. In his case, he tested the idea while keeping his existing business open.

Leaving the gasoline business

His career change started in 1980, after a difficult stretch in the gasoline business. During the 1970s, he had operated a franchised Clark Oil and Refining station in Milwaukee. He says the company’s efforts to remove franchise dealers and put salaried managers in their place followed a legal dispute that the dealers won in court. That shift left him looking for a new way to earn a living.

The dispute mattered to him as more than a disagreement over how a station should be run. A franchise arrangement can tie a dealer’s livelihood to decisions made by the company behind the brand, so changes in that relationship can unsettle plans built around the business. His account presents that period as the point when the station stopped looking like a reliable long-term answer.

He also wanted to move to a small town in northern Wisconsin. He considered buying two local businesses: a pizza restaurant and a liquor store. He negotiated a price for the liquor store, but couldn’t secure bank financing, so the deal ended there.

That failed purchase narrowed his choices in a practical way. He had identified a business he was prepared to buy, but a negotiated price didn’t mean he had the financing to complete the sale. For someone changing towns and trying to establish a livelihood, that gap between agreement and funding can be decisive.

Training while running the station

The alternatives nearby appeared limited. In 1980, he says, rural northern Wisconsin had few factory jobs, and those available paid modestly. Layoffs tied to changing economic conditions made factory work seem uncertain. At 28, he wanted a line of work that could provide more dependable income without requiring years of waiting for an opportunity.

That calculation helps explain why trucking drew his attention. Driving offered a specific qualification he could pursue, while the local factory market looked exposed to layoffs and offered limited pay. It wasn’t a promise of easy work; it was a route he could investigate while other plans were no longer viable.

He decided to qualify to drive tractor-trailers. His earlier experience offered a starting point: he had trained as a straight truck driver in the Army Reserve and had some familiarity with diesel engines. Still, knowing how to drive wasn’t the same as knowing whether he could handle trucking as a full-time occupation. He was unsure about doing the work day after day.

That uncertainty is a useful distinction for anyone weighing a move into commercial driving. Familiarity with vehicles may make training less foreign, but the daily demands of a job are another matter. The question wasn’t simply whether he could learn to operate a truck; it was whether he could make the work a career.

Rather than closing the station before he knew whether trucking would suit him, he enrolled at Diesel Truck Driving School in Sun Prairie, Wisconsin, and began training while continuing to operate the business. That choice gave him a chance to test the career before making the transition fully. For workers changing industries, training alongside existing work can provide a practical way to build skills while managing the risk of a new direction.

There’s a broader lesson in the sequence. Training can serve as a trial period as well as a route to a qualification, especially when a worker can’t afford to abandon current income before knowing what comes next. Here’s the thing: keeping the station open didn’t remove the uncertainty, but it let him approach the decision in stages.

A long career, with a difficult start

The training led to a 38-year driving career, which ended with his retirement in 2018. He describes the early part of the transition as having a couple of “stutter steps,” and says the work wasn’t always easy. Even so, he made what he calls a decent living over the course of his career and saved enough to retire comfortably.

Those “stutter steps” keep the story from reading like a simple success formula. The career lasted, but he doesn’t describe the beginning as smooth, and his account doesn’t claim that every driver will find the same outcome. The result depended on a combination of training, persistence and a willingness to take up work that remained difficult at times.

That experience offers a grounded view of trucking as a career choice. A commercial driving qualification can open a route into work for someone whose local options are narrow, but it doesn’t guarantee an easy start or smooth years on the road. In this account, prior driving experience helped, while training provided a way to assess the work and prepare for a larger commitment.

This is more significant than it looks: the story is as much about managing a transition as it is about choosing an occupation. He didn’t have a fully funded business purchase waiting for him, and he didn’t treat trucking as a sure thing before trying it. A measured start gave him room to find out whether the work could support him.

His story also shows how a career decision can be shaped by several pressures at once: a business relationship changing, financing falling through, a move to a rural area, and limited alternatives for stable employment. Trucking became the workable option after other plans failed, and it ultimately supported a career lasting nearly four decades.

What the experience says about career changes

If you’re working in this space, the practical point is that a career change often begins with constraints rather than a clean opportunity. A worker may have experience that transfers only partly, local options that pay less than hoped, and financial limits that rule out a preferred business. Training can make another path possible, though it can’t guarantee that the job itself will prove sustainable.

And yet. His experience ended with a long career and a comfortable retirement, even though the transition began amid uncertainty. That outcome offers a personal example, not a forecast for every new driver. It suggests that a deliberate entry into trucking can be workable when other routes have narrowed, while leaving the hard parts of the job in view.

Book recounts the experience

In 2020, he published a book about his experiences, My Truck Driving Life. It is available as an eBook, paperback, and hardcover through the links below. The book gives readers a way to follow the account beyond the career change described here, including the long stretch of driving that followed.

My Amazon Author Page

My Truck Driving Life