Trading a prestigious job known to occasionally turn down Harvard grads to go trucking isn’t an easy thing to do. But I did it. Sure, things like abundant college debt or feeling like you don’t really fit in with the corporate American business culture can make you feel the need for a drastic change. But in the end, those weren’t my reasons.

This longtime pink pant-wearing preppy traded in the boat shoes for cowboy boots and a freer life. What’s it really like? Is there a bigger goal in mind? What about all your suits and ties? Aren’t you going to miss your friends? These are the questions I faced, and so many more. Sometimes you just have to go to Walmart, buy some Dickies white tube socks, and make a change. That’s what I did.

Not long after I left the “normal” world of educated, middle to upper class folks, my friends became fascinated with the idealism of being able to leave the corporate world, so much so that I received tons of calls and messages wondering what it must feel like to be free from it all. That’s when I knew I wasn’t alone. I was living the dream alright, my own for a change, but I quickly discovered that my new dream represented something a whole lot bigger.

You’ve probably heard, “the mass of men lead lives of quiet desperation.” When Henry David Thoreau wrote those words, he had returned from life in the woods and was again living a regular modern life under the common comforts of a decent city dwelling, sit down meals, updated fashions, and regular conversations with friends and colleagues. But those words reflected his general discontent with living a life just like everyone else. He was recounting the meaning of his brief hiatus in those lonely woods, where he discovered that there was more to life than what most people thought. Whether or not it was pure privilege for Thoreau to take a break and experience something else, that’s beside the point. He stepped away from the “normal” for a moment to look deeper at the meaning of life, to decide for himself what was truly important. That’s what The Preppy Trucker is all about.

Let’s face it, most people don’t think twice to care much about truckers. This weird bunch of folks live in rolling boxes, they don’t have much money, they aren’t college educated, they don’t hold season tickets to ball games, and they don’t have résumés. Truckers aren’t normal.

To most people, trucking feels almost completely irrelevant. The average person might know if asked that trucking is important, but that’s about it. Behind the scenes, trucking does more for the average person than just about any other industry. The vast majority of daily-use goods arrive via truck, and most of those are transported by OTR (“over-the-road”) truckers. OTR truckers are the people you think of when you think of trucking. They drive 18-wheelers across the country wearing ratty t-shirts and greasy denim. They carry around two 64 oz. coffee mugs ready for regular mid-day refills. They hang out at truck stops, jumbo size gas stations with showers and laundry machines. And they eat at Denny’s. Truckers are the people “out there” on the road, and for the most part, they stay out there.

Life in the corporate fast-lane is about as polar opposite to trucking as anything else. It takes a lot for someone to trade pressed trousers and Eton dress shirts for torn up jeans and non-politically correct t-shirts. Before getting into trucking, I worked with some of the largest public and private organizations in the world. I’ve seen a lot of wardrobes and, by extension, a lot of people. But trucking is unlike every other experience I’ve had.

A recent article by the New York Times showcased a series of conversations with long-haul truckers from the central United States. It’s main point: truckers feel like “throwaway people.” Though the article does well to highlight the dismal, lonely life of over-the-road truckers, it fails to address the nuances of life-options available to them. Leaving the “lifers” (people who’ve been trucking for a long time, their only job) for another discussion, new entrants to the trucking industry these days tend to be immigrants or folks nearing retirement. These are the people who are forced to go into trucking because they don’t have many other options. And they’re not the only ones. These truckers are quite literally the throwaways of society.

The Preppy Trucker conceptually brings into focus issues like these to accomplish at least two things: 1) start a conversation that virtually nobody takes the time to start, and 2) craft solutions that can create better lives for an entirely forgotten subset of American society. This blog will drive down the life-roads of everyday truckers in hopes of making their lonely lives a bit better and more in sync with the rest of us (or us more in sync with them).

In a way The Preppy Trucker is a blend of two strangers: one like the deep inside of the protagonist of Billy Joel’s famous song and the other like the indifferent Meursault of Camus’ popular novel. The posts that follow will highlight some of the chains that bear weight on my own conscience about how our society works (and doesn’t) and will come from the powerful position of a true outsider. I didn’t come from a family of truckers. It wasn’t my only life-option. I’m more a parvenu of sorts, achieving a personal economic goal through leaching onto a foreign industry. Embedding my personal story within an analysis of the trucking world, each of my posts will look at controversial subjects to address many of the tacit assumptions people have about truckers and American life in general.

As you read, you may already be familiar with some issues. A recognizable discussion, for example, on autonomous self-driving trucks may seem familiar because of the presence of a similar public debate going on about self-driving cars. A likely more foreign example though, truckers suffer from an inadequate mail infrastructure. Tell me you’ve stayed up at night thinking about that. Many truckers would be considered “homeless” by a strict economic definition of the word. So how do they receive mail? How do they have credit cards? Bank accounts? Cars? The average American doesn’t face these issues, but truckers do. Deep infrastructural problems lie at the base of why truckers live the lives they do, and I will take a close look at them.

And that gets at exactly what a “preppy trucker” really is. It’s someone who examines something from the inside, yet while in ways remaining a true outsider. Get this. It’s really OK to wear pink pants and drive a truck. But why don’t we see truck drivers wearing pink pants? Because our world requires us to be practical, and that same world has different ways of prescribing what “practical” should mean in any given circumstance. Even more, why truckers don’t wear pink pants is coupled to broad, systemic things like economic and educational class status, race, gender, politics, and religion–all the things we’re scared of bringing up at the dinner table. Wait…truckers don’t have dinner tables. Well regardless, all these factors shape the trucking industry and how the average person sees it (or doesn’t).

So hop into the cab with me. We’ll be looking through pinstriped windows at a complex world of truckers and their everyday problems. Where a solution can be found, we will find it. I will aim at adding a new post every two weeks to pay justice to my cause and keep you excited about the issues. Your comments and participation will be much appreciated along the way. Please feel free to email me or publish respectable comments to the blog at any time.

Keep on preppy truckin’.


T.C. Dankers

T.C. Dankers

Sociologist, management consultant, entrepreneur, and blogger, Tom is the original “preppy trucker.” He sees things differently. Living the odd double life of both trucker and social theorist, he offers a unique perspective on a wide range of American business, culture, and social justice issues.


  • Tanya says:

    If your travels bring you down I44 half way between St Louis and Springfield, MO to a small town called St Robert, MO please look us up. Mike and I would LOVE to see you for a bit. Maybe even offer you a home cooked meal and/or a soft bed for the night. 🙂
    Blessings and Peace on your journey!
    Tanya (and MIke) Ryen

  • Regi says:

    So that’s “the long story”. I like it and will definitly stay tuned. Safe travels.

    BTW… you were very much misinformed earlier…

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