Rules of the Writing Road

About an hour east of Chicago, I looked at my college roommate, who was at that moment driving a large moving truck towing a car, and said, “There’s 106 miles to Chicago, we’ve got a full tank of gas, half a pack of cigarettes, it’s dark out, and we’re wearing sunglasses. Hit it.”

If you’re on a road trip, especially one anywhere in the general vicinity of the great city of Chicago, you’re pretty much contractually obligated to quote The Blues Brothers.

Whether you’re “on a mission from God,” hitting the road with your best friend to escape a sedate life, or headed to a drag queen pageant, road trips are the basis for a lot of stories, both personal and fictionalized.

Sure, people in other countries travel around by car, but the concept of a road trip is a uniquely American thing. In September 1957, Jack Kerouac published On The Road, which gave voice to a whole generation of writers and artists.

The themes Kerouac used in the novel — being spontaneous, open to adventure, not part of the “normal” crowd — are ones we still hear a lot about today.

The open road, after all, is all about being different from everyone else. It’s still a source of inspiration to writers and creatives.

When you’re a writer, the open road can be an opportunity to find stories or to create your own.

Kerouac would tell us to simply get on the road and embrace whatever happens; I find road trips work better in practice with at least a little bit of structure. So I have a few “rules” of the road that help me get to where I’m going and still have inspiring adventures along the way.

These five rules can help you experience life firsthand — and they can shape your writing, too.

Follow these rules to prepare yourself both for getting behind the wheel and for finding inspiration to write wherever you go.

Road Rule #1: Be Prepared

Sure, some of the best road trip stories come from not being prepared. But so do some of the worst stories (ahem, Donner Party).

Getting on the road for more than a few hours at a time needs a bit of planning. What’s your route? Where are you stopping? Do you have enough snacks?

Obviously, snacks are a priority (see above re: worst stories).

One day, I’ll find amusement in the story of standing in a parking lot at about 11 p.m., looking at one of the tires on the car trailer while my friend checked three different hotels within walking distance, finally getting the last room at the third.

You might not plan every stop, but you probably have an idea of how long you plan to drive that day and how often you need to stop along the way.

Knowing your route (or a variety of potential routes) is useful. Knowing where construction is and how to get around it is helpful. Knowing where the interstate roads are in bad condition (I’m looking at you, Indiana), and how to get around them, if you can, is good.

Road trips are, in many ways, about self-reliance. Can you read a map or make a nutritious meal out of things you find at a gas station?

Being prepared can also mean having time built-in to see things you didn’t plan for. Some of my best road trip stories start with: “Hey, what’s that?” Little farmers markets, the World’s Largest Truck Stop, gas stations with giant coffee pot signs and super fancy Japanese toilets: You don’t want to miss these random stops on the road.

Building some extra hours (or a whole day) into the trip can help you make sure you have time for those unexpected roadside adventures. The worst that can happen is you arrive a whole day before you’re supposed to.

It helps to be prepared when you’re writing, too.

It’s more than just having the right tools (pen, notebook, computer, etc.); it’s about having the right mindset. (And snacks, still.) A little bit of planning can make the inspiration easier to find.

Have a destination — that is, a goal — in mind when you write. Are you aiming for a certain number of words, a chapter, or the complete outline for your article? Knowing in advance how far you need to get that day, and maybe building in some extra time for detours, can help you focus on the journey.

What are you writing? Happy, sad, argumentative — put yourself in the right frame of mind for these emotions.

Where are you writing? Do you need a quiet space or some noise to help energize you?

A little bit of preparation can make the inspiration easier to find.

Road Rule #2: Be Flexible

Rolling along somewhere in upstate New York, my co-pilot and navigator said, “Huh. I think we missed Connecticut.” Given that the signs for upcoming towns said Buffalo and Syracuse, I think she was right.

Turns out, there are a few different ways to drive west from Boston, so our plan was to take a middle route through Connecticut.

Reader, we did not take that route.

Because we were prepared with maps, GPS, and multiple possible routes, it wasn’t a big deal that we accidentally rerouted ourselves. But ending up with a tire that needed to be changed the next morning really threw off our plans. An expected early morning and a big chunk of road under our belts turned into a half day to kill.

So, instead of sitting around doing nothing, we went to Niagara Falls. Because we’d missed Connecticut, we were only a short drive away from there. And we had the time, so instead of worrying about the tire, we distracted ourselves with something fun. In doing so, we had a chance to see one of the great sites of our country, which we wouldn’t have been able to do otherwise.

When you’re writing, stuff is going to happen, too. A chapter doesn’t turn out like you planned. Characters don’t behave. Editors ask for a complete re-write. Writer’s block strikes.

The best thing you can do is roll with it, even when all you want to do is find a nice quiet corner and fret over the time and effort you’ve lost.

Sometimes, you just have to say “screw it” and go have a little fun.

You might even find some inspiration from your unexpected change of plans. “What if” can be a great start to a story. And simply building the pathways of flexibility can help you think of ways out when you write yourself into a corner or when you discover a tangent in your story you really want to explore.

Road Rule #3: Be Open

A trope of road trip stories is unexpected encounters with interesting people. It might be a hitchhiking ghost, an asshole cop, or a whole town of good-hearted people.

In our case, it was a kind truck driver who helped us get out of a hotel parking lot early one morning.

We could have kept trying to turn that darn truck and trailer around, and he could have gone on his merry way, but instead, he took a few minutes to offer his assistance. He jumped in the cab of our truck and in no time, we were pointed in the right direction. We chatted with him for a few minutes, swapping stories, and then headed out.

Being open to other people on the road can be an inspiration. If we’re supposed to write what we know, well, most of the time, that turns out to be a pretty narrow swath of knowledge.

But when we take the time to listen and be open to the stories of other people, it gives us new stories to tell.

Really pay attention to your interactions with other people on the road. These moments can inspire you. Keep a journal with the details and with ideas that you have based on these little vignettes. Look for stories wherever you go.

Road Rule #4: Be Fearless

Across the country, when learning that we were driving a moving truck all that way by ourselves, people commented about how brave we were (though I think they might have had a different word in mind, but they were just polite enough not to say it).

And while road trips are often more fun if you have a Thelma to your Louise, solitary road trips can be a great experience, too.

It takes a bit of fearlessness to jump in a car and head off into the wild blue yonder by yourself. At the end of my cross-country road trip, I jumped in a car to head off in a different direction. I had an endpoint in mind, a couple of possible routes, and, of course, the all-important snacks.

It was 10 hours of driving round trip for a 15-minute stop, but what a stop. Seeing the solar eclipse from the path of totality was an experience like no other.

If I’d applied the rules of common sense (10 hours in a car to make a round trip of about 350 miles which should have taken no more than six hours with stops, by myself, in incredible traffic, not knowing exactly where I was going to stop, etc.), I probably would have said the trip was too difficult, with too many unknowns, too much potential for trouble, and the possibility that I wouldn’t make the path of totality.

But I prepared as much as I could, was flexible and open, and it turned out to be an amazing trip.

Being fearless can be a great source of inspiration. The confidence it takes to go someplace far away on your own or with one or two other people translates into having the confidence to take chances with your writing, some of which won’t work out.

That pitch you loved might not find a home. The perfect line in your novel might get cut by an editor because it doesn’t make sense for that narrative.

And it’s the confidence to get back in the driver’s seat when those chances fail or fall short. Send out that pitch again or craft another one. Take that perfect line and build a whole new story around it.

Being fearless doesn’t mean being careless. On a road trip, tell someone where you’re going and have a backup plan.

Same thing with writing. Be smart about the chances you take — if you’re going to craft a pitch, don’t just wing it. Do your research and make it a solid pitch. If you’re going to write a novel, set aside specific times to write instead of just hoping you’ll find five minutes here and there.

Yeah, from time to time being fearless means you’re going to get caught in a miles-long traffic jam. But keep your eyes and mind open; inspiration comes from strange places, and having the confidence to seize that inspiration will change your life and your writing.

Road Rule #5: Be Thoughtful

The open road is a great place to reinvent yourself or to figure out who you really are.

That’s the heart of almost every road trip story, right? Discover what you care about, who you love, or what you want to do with your life.

Even if you’re traveling with someone, you spend a lot of time with your thoughts, staring out the window. After all, there are only so many deep conversations you can have in 40 hours of travel.

Letting your mind wander gives it a break. If you’re like most people, it’s probably a much-needed break. You can’t check email or Facebook or Twitter while you’re driving. (Note: Please don’t do those things. Please don’t text, either.)

It’s you and the open road. There’s nothing you can do but drive and take in the natural beauty around you. Or the crowded cities. Or the cornfields (nothing but cornfields for miles).

It’s a great time to ask questions of yourself, of your traveling companion, or of the world around you. Observe and think about what you see or the people you encounter.

It’s space to listen to new things or go back to old favorites. Several years ago, somewhere along I-40 after starting out on the road at about 5 a.m., I discovered that the perfect time to listen to the podcast Welcome to Night Vale was when it was dark outside. Early morning, late night — either works, but there’s something about a dark and lonely road that makes this lovely show set in a small community radio station come alive for me.

Road trips are great for trying out new music, podcasts, or long audiobooks, assuming you won’t be too distracted by those things while you drive.

It’s also a great place to make up stories. The characters, who are the people you encounter along the way, or the settings you find yourself in, are all fodder for a creative mind.

For a Western-themed story, there’s inspiration in the Pony Express Museum or on the high plains of Wyoming. For a romance novel, there’s the cute guy at the next gas pump. For a mystery, there’s the collection of cop cars gathered on the side of the interstate for what looks like no reason.

Even when you’re not on the road, be mindful of what’s around you. Look for opportunities to step away from the “normal” routine of life and let your mind wander. Make up stories in your head about the people on the train or standing in line in your coffee shop. Listen to music on your evening commute or sit and stare out the window for a little while.

Let your mind roam the road with you, and who knows what you’ll come up with?

On the Road

Kerouac defined a generation of writers and creatives by using the road trip to explore the idea that life should be experienced firsthand, embraced with open arms and an open mind.

Writers have built on that concept for 60 years now with countless stories built on the idea of traveling long distances by car.

If you’re prepared, flexible, open, fearless, and thoughtful, your road trips will be fun and memorable. If you apply those same rules to your writing, you can find new ideas and inspiration on the road.