Except for a brief period, a few years ago. My wheels had finally found the ruts of a writer’s path: I had a viral essay and New York Times bylines. I had kneeled before Poets & Writers with a writing book and been tapped by their sword on my shoulder, included on their Best Books for Writers list. As a creative writer, a freelancer, and a trusty, older-sis-type coach for newbie writers, I had a map etched out. 

Then the universe shook my Etch-a-sketch. 

The pandemic, plus bonus tragedies that can strike at any time, because life doesn’t give you a reprieve just because your day-to-day sears subheads into the history books. The backsliding of my career barely registered as a blip. 

Last year, just as I was almost upright again, legs trembling beneath me as I tried to take steps toward something that felt like life, I relented and googled this ChatGPT thing I’d been hearing so much about. 

The pity party lasted three days. 

Luckily, around that time, I’d cobbled together a self-funded reporting trip that gave me something to look forward to. In my attempt to chase the travel writer dream, I’d arranged to hitch rides with teams of drivers on the Baja XL, a 10-day off-roading rally down Mexico’s Baja Peninsula. I would hop from Jeep to 4Runner to motorcycle, riding hundreds of miles a day, much of it through desert and rocks, totaling 2,800 miles, approximately the distance from Seattle to Orlando. 

I returned not only proud about what I’d overcome on the dusty adventure, but more confident about making it as a writer. I’d learned a particular attitude on this tire-patched and duct-taped trip. Overlanders, as they’re called, know how to create a path, even when it feels like you can barely trust the land beneath your wheels. 

In the weeks before the trip, I was haunted by the thought that throwing myself into the backroads of a foreign country with strangers with just a backpack was a terrible idea. If I were on the show Naked and Afraid, my Primitive Survival Rating would be about a 1.5. Two days before I left, I checked the online group one more time. A driver who’d arrived had posted about how damn cold it was. Last minute, I bought a sleeping bag rated for 20 degrees. In my tent that first night, my toes holding just below numb, I thanked my previous self for taking good care of me.

You can’t afford to mess up in the desert. Overlanders prepare as best they can, including first checking the weather. If we’re preparing for our writing lives, how do we do this? It’s keeping up with your community, learning from people who have been where you plan to go. 

If we’re planning to make a living as writers, I’d say it’s also looking for what futurists call signals of change — evidence that something will be different, and how it will be different. It’s the first emoji you see in The New Yorker, the first time you see a job post for an AI prompt writer, the first time you recognize something as written by an algorithm. These indicators are to futurists what plot points are to writers: the building blocks of a story.

The weather determines the gear you’ll need, and, as writers, our gear lives mostly in our minds. That’s why, on top of reading and writing, I try to learn something about the business, the tools, whatever gets me traction, at least a little bit every day. I’m upgrading my gear, turning myself into a more powerful vehicle to climb my wilder, more ambitious artistic mountains and keep myself fed and housed and insured along the way. 

How you prepare depends on your resources. One Baja XL driver brought a fancy rig with a $9,000 suspension, and another vroomed in driving a police-car-auction Crown Vic with zip ties holding the bumper together. Some had day-job budgets; others had mechanical knowledge gained over decades tinkering under hoods. Once you’ve prepared as best you can, make do with what you have. 

So often, I’m pouty or paralyzed because I couldn’t afford the fancy MFA or couldn’t pay my bills if I wrote as many hours a day as I’d like. Cheryl Strayed’s words slapped me hard when I read, “You don’t have a right to the cards you believe you should have been dealt with. You have an obligation to play the hell out of the ones you’re holding.”

You have an obligation. 

If your tools include a steady income, take writing classes. If you’re rich in community, arrange a workshop with writer friends. Every moment spent envying the writing life we could have had, if only — and I say this as someone who mentally swats at those moments like mosquitos — wastes the opportunity to get creative with what’s in front of us. 

The word scrappy can mean determined or it can mean made from scraps. My writing life is both. 

On the second day of the rally, a team pulled up next to a fellow off-roader and leaned out to greet him. 

“Hey, you’ve got a flat tire,” someone from inside the vehicle pointed out.

“Oh,” he said, “you do, too.”

No one was surprised. They expected the rocky desert to do what it does, and they brought spares. They planned to spend time with a knee in the dirt, wrenching off lug nuts. They brought gloves. 

Writers are not on life’s main highway. We have veered off where the view is spectacular but the ride is rough. The flat tires of rejections are part of the deal, along with writer’s block, crumpled-up starts, existential flails. 

In the software I made to organize my writing life, a graph tracks my publication attempts. The line for submissions rises high, hugged closely underneath by the one that tracks rejections. Acceptances form tiny bumps.

This is the fun we’ve chosen. It’s not fun like drinking beer and playing video games might be fun; we have to work to get that sense of satisfaction, trusting that the trail of flat tires behind us will make the summit all the sweeter. 

And we can’t be shy about how hard it really is, or how much harder it might get. 

Even the founder of the Baja XL, Andrew Szabo, who named his company The Institute for Unsafe Living Ltd., brings along a medic, prepared for the worst case scenario. One of the most well-respected drivers, Dave, has been known to bring a spare drive shaft, among other parts. It covers one of the worst-case scenarios.

I want to tell writers to be optimistic, but that would be as irresponsible as crossing your fingers and hoping no one rolls a Jeep off a cliffside. So I embrace the Stockdale Paradox. 

Admiral James Stockdale was the highest ranking officer in a POW camp for eight years. When asked afterward how he made it through, he said, “I had unwavering faith that I was going to make it in the end.”

When asked who didn’t, he said, “The optimists.”

The optimists were sure they were going to get out by Christmas, and then Christmas would come and go. Same for Easter, Fourth of July, Thanksgiving, for years. But how was Stockdale different? 

“I also never shied away from the brutal facts of our reality.”

And so the Stockdale Paradox instructs us to maintain unwavering faith that we will prevail — finish this novel, publish that chapbook, live the artist’s life — regardless of the difficulties; and, at the same time, it tells us to have the discipline to confront the most brutal facts of our current reality.

The reality is, I don’t know what AI is going to do to my creative or freelance writing career. I don’t know what the future of books looks like. 

But I have a plan for the worst case. AI can’t coach writers, lead retreats, or build community like I love to. I can actually play the corporate game quite well, if it comes to that. I can cook. 

Looking the worst of it in the eye gives me a sense of control and calm. 

I didn’t land the pitches for the Baja XL piece I’d envisioned. I wrote it anyway, on Medium. I’ll be a traveler, and I’ll be a writer, but it looks like I’ll have to do it my own way. 

Riding with a crew that had teamed up in a string of half a dozen trucks, we came upon a few motorcyclists stuck with busted wheels. Everyone pulled over. We stood in a circle, offering advice, patches, a hand to brace the tire against the rim while the bond dried. We hung around for more than an hour, just helping and hanging out. No one got left behind.

Before I started my online writing group, A Very Important Meeting, and became a part of that community, I used to think that I, as an artist, had to be the singular flower in the vase. (And of course, it would be a humiliation to be anything less than the most award-winning flower.) But seeing everyone write together and afterward commiserate or celebrate helped me see myself as just one in a swath of wildflowers, all blooming on our own time. I was able to enjoy other people’s success and feel more supported in my own struggles. We can at least make each other laugh about it all, and offer to listen, towing each other out of the sand of self-doubt.

Ocean Vuong reportedly encouraged students to think of competitiveness among artists as a racetrack, something synthetic. Remove the man-made elements, the enclosure and the numbers, and all you have are horses running in a field. 

The camaraderie of the road is not only the joy, it’s the comfort, the ability to give when someone needs help, to ask for it when you do, trusting that someone will stop with you, make sure you don’t get left behind. 

I was riding with Andrew, the creator of the rally, to the hot springs one day. The road there, however, was not, indeed there. In the desert, the land moves. 

This was the refrain of the trip: 

“Is this a road?” 

“Are we on a road?” 

“Where’s the road?”

“Where’s the road?” is the essence of what writers are going through right now. We’ve thrown it into park, and we’re standing in front of our idling cars, hands shielding our eyes from the sun, staring at a pile of rocks, saying, “There used to be a road here.” 

I’m writing in the morning, doing client work, coaching writers, designing software, reading in snippets, reporting a bit, running retreats, teaching classes, sharing a one-bedroom in New York — is this a road?

One of my favorite quotes from Game of Thrones is: “Chaos isn’t a pit. Chaos is a ladder. Some are given the chance to climb, but they refuse. They cling to the realm.”

I can be guilty of clinging to the realm. I want my ’90s publishing budgets. There used to be a road there. 

We are tasked, then, with making new roads. Perhaps it’s taking a corporate job so you don’t have to think about money, waking up at 5 a.m. to write. Perhaps living cheaply in a tiny place or somewhere rural. Hell, it could be starting a side hustle as a wood soup ASMR influencer.

You might be flinging up sand and dirt, branches thwacking your windshield, saying to yourself, “I don’t think anyone’s come this way before. Is this a road?” 

Overlanders know: If you can make it a road, it’s a road. You make it one by driving it. 

At camp each night, Dave unhooked the yellow jerrycan — a color that’s supposed to signify that it contains diesel — from which instead he poured everyone margaritas. 

Along the road, we passed an SUV with a gigantic inflatable rubber ducky strapped to the top, smiled every time. 

When we saw an especially gorgeous view, we stopped to just breathe it in. 

Not everyone made it to the finish. Axles broke and teams disbanded. Sometimes all people had were the first few days. 

Not all of us will make it in writing, either. Amid my career in short form, there’s this novel I’ve spent about a decade trying to get right. I don’t know if I ever will, but I’m comforted by the times I’ve made myself cackle at my desk. I’m simply enjoying the view.

I know we writers are a very serious bunch, but as it turns out, having fun in your work has been shown to help you get more done and do it more creatively. Fun provides solace when you consider that our performance might only pay off in the moment it’s lived. 

This year the Baja XL was missing a driver. Dave’s friend and former teammate, Phil, had died of Covid. Dave and a few other drivers carried a memento mori coin, which some had made into a keychain. The front had a skull and an hourglass. The back said, “You could leave life right now.”

We have no idea how long our roads are. So whenever I’m stressing, which is only multiple times a day with a nightcap around 3 a.m., I try to remind myself to come back. Don’t worry so much about the destination. Celebrate the little wins along the way. Enjoy the company. Eat a taco. Make it a road trip. 

The most entertaining driver I rode with, Wilson, told me about how he had planned a trip to Baja outside of the rally with just one other friend. Five days before they were set to head down, the friend told him, “This is just so far out of my comfort zone that I’m just, I’m freaking out.”

His friend backed out and Wilson went alone, which he could do because he’d already been, had already pushed himself past the freak out, expanded what he knew he could handle. 

I was also freaked out about going to Baja, and now all I want to do is go again. I was scared to pursue a writing life, but having figured it out up until now gives me the confidence to continue making my path.

You may have heard the E.L. Doctorow quote, “Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.” Off-roading told me: You can only see the road or the rocks in your headlights now. You can only make a path with the tools and the friends you’ve brought along. But you’re going to make it that way, trusting yourself to do the best you can with what you’ve got, taking care of yourself and fellow writers on the path, and rerouting when you need to, to create your most important story — that of the writer’s life you’ll live.