The Heuristic Traps of the Writing Life

why do we do this to ourselves?

Last week I did a bunch of research on going back to school to be a high school English teacher. A month ago it was nursing, but then I panicked about being bad at math and how a simple mistake in nurse-math can kill someone. No thank you to that. Teaching seems like another impactful option. Life-or-death situations are tragically not absent from schools, but at least they’d never hinge on my ability to do math without a calculator.

This happens every six months or so. Doula, physical therapist, arborist, lactation consultant, tradesperson of some sort… I’ve flirted with possible career changes again and again. I even wrote a feature on career changes as an excuse to ask people about theirs.

This panicky urge arises at moments in my professional life when the path suddenly quakes or crumbles beneath my feet. I lose an anchor client. I spend hours on a pre-reported pitch that goes unanswered. An editor ghosts me after asking a bunch of questions that made me think they were definitely interested in my pitch. Then, perhaps, it’s time to veer off, to go looking for more stable ground: a new dream, a new set of goals, a new kind of work with guard rails like health insurance and paid vacations.

Inevitably, my panic circles back to the fact that I love writing. It’s the only thing I’ve ever really wanted to do. And I really like the freedom of working myself. I need to work for myself to if I want to pursue the stories I’m most passionate about! And Blah blah blah. (I roll my eyes here at my own impassioned self-destruction.)

But let’s back up. Take a deep breath. I’ve been here before.

I know how to hustle. I know how to struggle. I’ve known stretches of success, and I’ve made it this far. Why not keep going? I can almost—I think—see the summit from here. And the summit looks like a big story that leads to a book deal. Or a viral Substack post that turns these many hours of barely paid labor into a dependable income stream. Surely, one of these breathtaking vistas is just around the next bend. So I put one tired foot in front of the other and keep trudging forward.

So many of us do, leaving footprints of encouragement for others to follow.

A very fun but very hard run around Mount Saint Helens, just doing whatever the runners in front of me do.

What we can’t see on our professional writing paths

If you happen to be a mountaineer or backcountry skiier or a hiker, you might be familiar with heuristic traps. I didn’t know the term until a recent episode of the You’re Wrong About podcast in which Sarah Marshall and Blair Braverman talk about Aron Ralston, that guy who was pinned by a fallen boulder in a Utah slot canyon and had to saw his arm off with a multi-tool.

Braverman explained that heuristic traps are cognitive shortcuts we develop through experience and confidence, applied inappropriately to challenging situations. In outdoor pursuits, quick decision-making based on cognitive shortcuts can lead to terrible consequences—like needing to saw off your arm.

While experience and confidence are often good things, heuristic traps propel us forward despite conditions that should give us pause.

Here are a few examples of heuristic traps:

Commitment. You’ve planned to do something, so now you must complete the task. You push forward on a big hike because you told people you were going to summit today. And you’re not a quitter, so you’re going to do it. Even though you just saw a flash of lightning in the distance.

Familiarity: You know this route, so you can do it again. A familiar path offers a sense of safety, even if something unexpected changes everything. When you start to feel sick or run out of water, halfway to your destination, you tell yourself to keep going because you’ve done this before so what’s the big deal?

Social Proof: You’ve seen other people do it, so you can, too. The trail is marked. There are cars in the parking lot. Certainly, if all these people can handle a rain-slick, scrambly summit, so can you.

Now that I know about these cognitive shortcuts, I’m seeing them everywhere, especially in my work. Probably because conditions haven’t been great lately.

The edge of a trail I know well.

I just spent the last two weeks anxiously refreshing my email every thirty (er, ten?) minutes, waiting for the details of a big book project that would have filled my whole summer. When the editor finally let me know this project is being postponed till next year, she signed off with a chipper, “I hope this frees up space for other projects you’ve put on hold!” which almost made me cry because the truth is—I don’t have any.

Since leaving a full-time job and returning to freelance writing last year, in preparation for my family’s cross-country move, work has been so slow. I thought I’d jump right back in. Reconnect with old clients, pitch editors who know me, relaunch this newsletter. But things have been so much harder than the last time I was freelancing. The old clients aren’t producing new content right now, and if they are, there’s a good chance AI is involved. Editors I’ve written for have started freelancing themselves or moved to beats I don’t cover. And there are approximately 10,000,000 Substacks now, all vying for attention and $5 from readers who are probably writers, too, and therefore unlikely to have a ton of expendable income.

I’ve already pivoted to looking for full-time writing work again. But even the jobs I’m overqualified for have 100+ applicants on Linkedin, an hour after being posted. And I still send off my cover letter into a distant field of crickets.

So. What’s a committed, passionate, experienced writer to do?

If you hang out in groups of writers (in person or here on Substack) then you probably receive a lot of advice about persistence and the feast-or-famine nature of this work. Encouragement, you might call it. Or, you could call it a heuristic trap.

In writing work, the heuristic trap of commitment might look like that journalism degree you’re still paying off, or the fact that you’ve been telling people about the book you’re working on for years now. Familiarity might look like your comfort level with the ups and downs, telling yourself this is normal because you’ve had slow stretches before. Social proof looks like the many stories of success, the writer friends who are still out there pitching and publishing, the debut books hitting bestseller lists, the many Substack notes about sticking with it till you’re 60 and finally getting a book deal. (Nevermind the decades of crippling financial anxiety that get you there.)

Guess which path I always take?

I am familiar with the hustle. But ten years ago, I did things like rent my house out on Airbnb and move into a campervan for weeks at a time to save money. I can’t do that with a three-year-old. She would like to take a tumbling class this summer. My husband and I would like to take a vacation that involves really nice pillows.

Maybe part of why we love calling ourselves writers is because it’s hard. Look at us, doing the hard things because we are so committed to our craft.

The truth is, I’m tired of hard.

Then again, I know for most of us it’s also about the stories and the truths we only know how to reach through a persistent reconfiguring of language and ideas. Stories require conflict and tension. A narrative arc can not exist on flat, stable ground. Again: Bring on the hard. Eventually, it feels so good.

So here we are! Steeped in an industry that has been in crisis since before many of us arrived, working on hard stories about hard things, telling each other it’s ok if an editor doesn’t respond to your pitch—it has nothing to do with you and probably nothing to do with the story, even! Just keep trying. Credit card debt be damned.

I’ve added to this rallying cry as part of my own newsletter brand in the past, encouraging fellow writers to keep pitching, keep applying, keep at it, despite the challenges. But I don’t really want to do that anymore.

I’m not walking away to become a nurse or a teacher just yet. But I am looking at the freelance writing landscape more critically than I have in the past. AI is completely reshaping our industry, and I know it will continue to do so faster than I care to pivot. I still stand firmly in the camp of Not Touching ChatGPT, or whatever large language model people are playing with these days. On this point, I don’t buy-in to adaptation being key to survival. But that’s a topic for another day. (Basically, what Tove said.)

I realize admitting that writing work isn’t working for me lately is not a great look for someone with a newsletter about writing. But I’ve never been here to tell you how to make it work. I’m here to be honest about what it looks like along the way.

Place-based writing, in this case, is about the feeling of exhaustion and desperation as you make your way to the summit. But it’s also about noticing the view. There are still birds and wildflowers along the way. Maybe we should be paying attention to those things, and spending less effort on a specific destination.

I went to a talk to the other day with Laura Marris, author of The Age of Loneliness (a gorgeous book I’d like to write more about soon), and she spoke about the importance of ground truths. When reliable radars tell us that a storm is approaching, it’s still important to get someone out there, on the ground, to confirm that clouds are indeed rolling in—that it actually starts raining.

Each of us is the only one who can see the ground truths of this writing life for ourselves. Substack and other digital writer hangouts will always be pumped full of advice and encouragement most days because we do need those things from each other. But then you have to go back to your real life and see what’s working. What did you actually get paid, per hour, for that big story you spent months on? How much unpaid labor are you still devoting to the work of placing stories? Are you happy?

There’s no arguing with the precarity of making a living as a freelance writer these days. There are fewer and fewer publications to pitch and the whole industry teeters on a pivot point of mistrust between conflicting realities.

And yet, to reevaluate our professional options might be more like stocking up on supplies than returning to the parking lot. Because fine. I hate the burn of this incline but I love the fresh air and just being out here. I love the one story I’m working on, even though it’s doesn’t pay enough and I won’t see that paycheck for at least a month after I hand it in.

Maybe we should drop this hiking metaphor?

Maybe. But first, there’s another heuristic trap I haven’t mentioned.

The Expert Halo trap, which is to place too much trust in the opinions of experts, even when they are no longer relevant. Like how I never pay attention to directions when a knowledgeable friend is leading the way on a windy network of forest trails and suddenly I have no idea where we are or how to get back to the car. You could apply this to the saturation of writing advice on Substack. But I think I might also be Expert Halo-ing myself out here.

You see, I have done the hustle-and-struggle and write-my-little-heart-out thing for so long, that I’ve gotten used to it looking a certain way. I have become some kind of expert in a very specific way of doing things as a professional writer. My formula has always looked like a few journalism pieces a month backed by a regular content writing client who probably found me through a referral.

I know one path really well, and I just keep going back to it, even though there are dozens of trails out here.

Times have changed since I was last freelancing. And there’s still a whole freaking forest out here to work and play in. We’re not on a steep, single track trail making our way to a singular summit. We’re just trying to be professional writers who make enough money to live comfortable, happy lives and do work we’re proud of, frolicking in the endless expanse of stories and different ways to be a writer.

It might be time to look beyond my own expertise. It’s definitely time to cold pitch some new clients, revamp my website, and consider different types of writing work that free me from the anxiety of bills and make brain space for more creative projects.

Regardless of what happens next, I don’t regret the journey that led me to this point. Despite all the frustrations and stress, this is a very cool thing about being a writer: No matter what mix of writing work you’re doing, it’s your job to be curious along the way. You meet new people and ask them questions and do new things and gain new knowledge and stumble upon new ideas to be curious about. Even if it’s in pursuit of a modest paycheck and not a beautiful piece of writing to live at the top of your portfolio, you’re always learning. Every single thing we collect on whatever path we take—whether it’s mountain path or city sidewalk or bushwhacking through a field!—becomes the ground truth of our writing work. We just have to stay aware and take in the whole picture. Enjoy the view and watch the weather.

I might still become a high school English teacher someday. Or some other profession I haven’t thought of yet. Today, I’m going to keep writing. But I don’t mean for that to be encouragement or advice. It’s just what this weeks looks like, on the ground of my own writing life. I’m also looking at the surrounding landscape more critically, and I’m trying to stay aware of the risks, without relying too much on an assumption that I can handle this. I might not want to stay on the hard path, even if I can. Regardless, I know I’ll never not be a writer. Maybe when I stop pushing for the summit, I’ll catch my breath, look around, and some captivating detail will come into focus, and it’ll make for a really good story.

Upcoming Deadlines

The Master’s Review Best Emerging Writers 2025 | Submit by 6/9

Artist Trust Grants for Artist Projects | Apply by 6/23

Essential Voices Editorial Fellowship | Apply by 7/2

Writing the Unseen: Multi-genre workshop with Laura Marris | Apply by 6/5

David Burnham-TRAC Data Reporting Fellowship | Apply by 6/16

Ucross Residency | Apply by 7/25

Willapa Bay AiR Writing Residency | 8/25

Events and Education Opportunities

• The National Press Foundation is hosting a webinar on How to Cover Education Cuts In Your Community on June 10.

• The Pulitzer Center will present the webinar Unburdening the Climate Generation on June 11. “The event will begin with a short discussion among panelists on what it takes to defend climate research, support Gen Z in tackling climate issues, and the oversimplification of the term "climate anxiety." This sounds so important and interesting and I will definitely be there!

• Talking Travel Writing and Adventure Travel Networking will present From pitch to publish (and everything in between): What can writers AND editors do to improve the process? The webinar takes place on June 18 and costs $8.

That’s all for today friends!

Stay inspired,

Britany