The disappearing dream of a writing career

Watching the ladder crumble. Figuring out plan b

The biggest break I ever got as a writer came one night in late 2015.

I’d written an essay about my mortgage payment for a tiny personal finance website called The Billfold, and that evening, my Facebook inbox pinged with a DM. It was from a senior editor at New York magazine.

“Pitch me,” she said.

This was a big BIG deal because, at that point, I’d been pitching freelance articles to major media outlets for years. And getting nowhere.

But the DM changed everything. I sent the editor some pitches the very next morning. She took one, slating it for The Cut, the magazine’s women’s vertical.

That essay—about, of all things, my blond highlights—went modestly viral. If I recall correctly, the editor told me it got around 200,000 views in its first 24 hours.

A check for the princessly sum of $400 arrived. So did my first-ever bits of internet hate—spitballs lobbed via Twitter, comments sections, and the sort of piggyback/reaction pieces that Yahoo! published a lot of in those days.

I shared this clip in emails to other editors. I started getting more responses. Pitches accepted at more places.

Eventually, I got a book deal on the back of another modestly viral essay, all while I slowly, slowly racked up the bylines I’d craved for so long. Oh my God, so long.

Slate. The WSJ. Lit Hub. All the outlets of my wildest freelancer dreams, or at least some of them.

If you’re thinking “hmm, this sounds like a story she’s told before,” you’re right. A lot of writers—especially those about my age, generation, gender—have a similar story.

My point is that I climbed a certain career ladder. As far as I could tell, it was THE ladder—the only way to establish the literary career I wanted. Back in the roaring 2010s, there were these online publications paying for essays, i.e. a market. Likewise, there were various cool-girl writers producing such essays, and I envied their careers, how they sometimes wrote about their own lives and at other times published more esoteric sorts of essays, journalism, novels. I’ll have what she’s having, basically, that was my thought.

This media phenomenon became known as “the first-person industrial complex” and it grew semi-notorious enough to be mocked on the HBO series Girls.

You wrote about your life for print but mostly internet publications, on a freelance basis. Depending on how lucky you were and how entertaining or provocative you were, you might also get rewarded with bigger opportunities. A staff job. A deal for a whole book of essays.

While dubious, deeply flawed, only ever a quasi kind of thing, this career path did have one advantage: It existed, like at all.

And not even that long ago. We’re speaking of the recent past, people! Not 1979. Not 1992. Not 2006.

But now the text-based internet has given way to the video-first internet, and many of the publications I once contributed to (or only hoped to contribute to) have gone dark. Died out. The media business has bottomed. B O T T O M E D. Several months ago, the two big freelance-opportunities newsletters consolidated, which tells you how many such opportunities remain.¹

Leigh Stein, the novelist and newsletter writer, put a fine point on it when I interviewed her this past June, saying:

“Today, pitching and publishing essays in digital media outlets gets you nowhere.”

She went on to say that your time is much better spent building your own audience. Maybe through Substack, or TikTok, or another platform.

Is she right about this? Yes, of course. Abundantly. The value of audience-building was clear to me before, but watching my interview with her become, overnight, my most-viewed post ever, it just got clearer to me. And this when I’m part of her audience myself. Her Substack is the best one about this topic: how to have a creative career, right now.

And yet! I still struggle so hard to put her advice into practice! And the reasons multiply the longer I brood over them. I don’t love publishing anything without an editor. I spent years honing skills that are now at least in part superannuated, anachronistic. Doesn’t feel great!

Also, the newer way of doing things makes for a fuzzy diagram. What’s the ladder? Where’s the path?

Maybe that resonates with you.

This is a very easy historical moment in which to feel as if the ladder is disappearing, and with it, the dream. AI is changing everything so completely and so rapidly that I don’t really need to do more than handwave at it here, do I?

But the longer I sit with my resentment, banging pans together in my mind, the more I realize the ladder is always disappearing. It’s always disappearing. What is always disappearing? The ladder. And not just because there is no more reliable phenomenon than changing content models, but because the sensation of the ladder disappearing is the sensation of having a career. It’s less a description of circumstances than it is a description of your personality in contact with your project, whatever your project may be.

Like Tennyson wrote in “Ulysses,” my all-time favorite poem:

Yet all experience is an arch wherethro'
Gleams that untravell'd world whose margin fades
For ever and forever when I move.

Translation: If you’re a striver, your fate is to somehow live with the feeling that all your best chances are evaporating and that there’s so much more you want to accomplish, all while time is slip-sliding away and the hour of our death approacheth like a pizza in the Domino’s Tracker.

Related: If I’m honest with myself, I felt the same damn way in the 2010s. The path forward has never been clear. Not really. Not for any length of time.

Such is the territory, the whole deal. My feelings of hideous defeat, imminent doom, and bottomless, craven hunger? Your feelings—if I may presume—of hideous defeat, imminent doom, and bottomless, craven hunger? They’re the attention-economy equivalent of Nietzsche’s eternal return. More generally, the business of making stuff is not a venture that’s going to make you feel all fuzzy, warm, and totally secure. You keep going, anyway. In fact, here’s Tennyson, in the last line of the poem, urging us on:

To strive, to seek, to find, and not to yield. 

I cannot tell you how many times I’ve muttered that line to myself in moments of crisis. More than 1,000,000,000,000. It’s so stirring. So resoundingly iambic. I unironically suggest you try muttering it to yourself in moments of crisis, too. Can’t hurt.

Meanwhile, back at the ranch…

The first-person industrial complex is dead. Long live the first-person industrial complex.

Would you believe that as I was slowly drafting this post, this whole topic went viral? A couple of Substack posts made the rounds in a big way, talking about how the old media world, long threatening to give way to the new media world, has finally, for real given way to the new media world.

Ted Goia wrote about the death of magazines, which he argues is not the same thing as the death of journalism. Emily Sundberg wrote critically about the sort of posts that go viral on Substack, essentially identifying Substack as the new version of the first-person industrial complex, the new version of blogging, and the new version of whatever came before blogging. And for us practitioners, Leigh Stein wrote about writing vs. content. A useful distinction.

Thank you for reading, as always. I’m wishing you the best with your striving, seeking, finding, and not yielding.

Cat

P.S. One more link: If you’re an aspiring nonfiction author, you should check out the newly released book Hungry Authors. Ariel Curry and Liz Morrow have put together a fantastic guide to both writing and selling NF. Highly recommend.

1. All this has arguably been true for at least 10 years already. It’s just more true now, has never been truer, etc.