On deBoer on Tolentino

Who can afford to be ambitious when all we have is posting?

Pete Tosiello
13 min readAug 5, 2021


A ~trick mirror~.

Although the apology post has since been removed for dubious reasons, to the best of my recollection it boiled down to this. In the heat of bipolar mania, Freddie deBoer, a socialist academic and prolific essayist, falsely accused a fellow writer of sexual harassment; the hoax was swiftly exposed, and deBoer retreated into self-imposed internet exile, promising to seek treatment. Like much of the last half-decade, my memory of this incident lacks any real texture — I can’t tell you where or when I read about it, and little evidence remains, the offending posts and reprisal long since scrubbed from their feeds. It was a grisly episode, but I can’t say I was especially upset. While I’d enjoyed the work of both deBoer and his target, their personal lives impacted mine only insofar as they were successful internet writers and I was not, and surely there were any number of genuine atrocities occurring on the same website that day. I’m trying to be better, too.

I think I first became aware of deBoer because we grew up in adjacent New Haven suburbs, and his writing on Connecticut’s faux-liberalism resonated with me around the time my childhood friends started applying for their own country club memberships. As a younger reader, I liked him for the same reasons I liked Richard Ford and Frederick Exley: he was a warts-and-all writer who left it all on the field, even when you wished he wouldn’t. Although it is, again, expunged in its original context, I remember his apology (and his subsequent musings on the subject) struck me as patronizing, not because I’m unsympathetic to his plight, but because it was one of those circular non-apologies. My mental illness makes me a herculean poster capable of churning out 10,000-word treatises overnight, which is good; it also makes me a vindictive troll, which is bad.

Anyway, to invoke what was surely the tagline of at least one Nightmare on Elm Street sequel, Freddie’s back. His Substack is going about as you’d expect: he posts intermittently perceptive stuff and is in desperate need of an editor, a friend, or both. He seems to relish his new status as a Shitty Media Man, writing diatribes about Sarah Jones and Lauren Oyler while unable or unwilling to name any of their male peers. There’s a lot of Yglesias karaoke that reads as reactionary for reactionary’s sake; he gets so worked up about free speech and identity politics that he inevitably has to backtrack and swear that he doesn’t actually hate women. Once in a while he posts these squeamish bloodlettings about how antipsychotics turned him from a bodybuilding, sex-addicted Adonis into another whiny fat guy, an individual penance meted out by a wrathful God. The whole exercise feels like a meta-commentary on this fretful moment: a disgraced member of the once-ascendant Online Left is drawn back into the maw of outrage blogging, tail between his legs, because his mental illness—itself triggered by exposure to the internet—renders him otherwise unemployable.

How it’s going.

When his free posts turn up in my inbox, I find myself cursoring over with skittish absorption. There’s a nostalgic element for sure, but for all his grouchiness his prose style remains thrilling. He’s so long-winded that he tends to sneak up on you, and then a million lightbulbs go off in your head because he articulated this suddenly obvious thing you’d felt deeply but couldn’t put into words. I haven’t encountered his brand of verbose argumentation anywhere else on the internet — at his best, he could convince you of practically anything.

When political contrarianism is not turning you into a lunatic.

So it was with some reservation that I opened his recent 6,000-word essay on Jia Tolentino, who is exactly the sort of younger, more popular, more telegenic, more…well, feminine writer who incurs deBoer’s ire these days. His career envy manifests in the usual ways, but I appreciated the way he articulates Tolentino’s peculiar talent:

There’s this constant presence of self-deprecation in Tolentino’s work which is straightforwardly phony — she, the writer, and you, the reader, know precisely how estimable she is, and you both know these swipes at humility are fundamentally bogus — and yet which is charming nonetheless, which is a real accomplishment. I say that with zero cynicism, truly. False humility should be deadly for anyone, but I think there’s a certain verve in Tolentino’s best work that compels you to admire her for advancing a critical reading of herself that’s so transparently untrue.

This is classic deBoer, building a head of steam with breathless sentences so long you forget what they’re about. Although his assessment of Tolentino’s “charm” and “verve” feels characteristically objectifying, I think he’s getting at something most critics—especially the ones who likened Tolentino to Didion and Sontag—didn’t grasp. Tolentino’s greater project, if she can be said to have one, is calling her own bullshit; she knows that writing is a narcissistic endeavor, and sometimes she fucking hates herself for it.

This tension propels Trick Mirror, which is at its core an apology—an apology for being young and brilliant, an apology for being a sorority girl and a Peace Corps volunteer, an apology for being an attention-seeking blogger and an American. By her own account, Tolentino was a preternatural beneficiary of Web 2.0’s self-promotional incentives, selling herself out before she even knew what she was doing. Trick Mirror is a riveting, heartbreaking book because Tolentino knows that she’s cursed to contend not only with her own phoniness, but with the vapor trail she’s left across the internet.

deBoer’s main gripe with Trick Mirror is that it’s a genius on autopilot, and I guess that’s a fair criticism, if only because we’re conditioned to receive literary debuts as go-for-broke manifestos. It’s true that it’s a book of personal essays by the writer who’d declared the death of the personal essay 30 months prior. deBoer cites a 2015 piece in which Tolentino admits to scrapping an early novel about her experience in the Peace Corps, and suggests that her cowed diffidence is emblematic of a generation of internet writers:

We are to take it as given that the title of her failed novel, The Earth is a Small Place for Fugitives, is achingly pretentious, and as it’s taken from a Kyrgyz proverb, I suppose it’s cultural appropriation or whatever the fuck we’re into these days. Personally, I think it’s a lovely name for your first book. Yes, it announces ambition. But then, that was once the purpose of first novel titles, to announce something to the world that you couldn’t take back. No more. Now such titles are for ironic deflection of the embarrassing reality that the author is such a pompous creature that they would publish a first novel and take it more seriously than a TV recap.

Again, fair enough—deBoer would rather Tolentino grapple with, like, globalism than with last month’s memes. But still, “announcing something to the world that you can’t take back” is kind of her whole thing, right? She’s Jia Tolentino!

Like Lauren Oyler’s takedown from 2020, deBoer’s essay drones with the latent implication that Tolentino is too cool or too frivolous to be an important writer, that in her popularity she’s been co-opted by institutions and grown too big to fail. I don’t think this charge is worth anybody’s time—once again, I’m shocked that a white person can write 6,000 words on The Unbearable Privilege Of Jia Tolentino without once using the term “woman of color”— but deBoer’s fiercest critique is that Tolentino is, like most of her peers, too cynical and browbeaten to attempt a work of literary merit:

Give me the ambition of 2010 Jia Tolentino, not the sad indifference of aspiring Inside Hollywood host 2021 Jia Tolentino. For fuck’s sake, ambition in a writer is good. The pathetic literary culture we have today, with its allergy to the most basic desire to do great work and the endless ironizing of the artistic esteem that writers both desperately covet and showily reject… who is it for? What does it serve? Do you know how rarely books earn out now? Why not call your shot and swing for the fences? This endless disdain for wanting to write good and important stuff is not helping anyone.

For someone with deBoer’s socialist cred, I’m struck by how romantic this is, and how shallow its material analysis. Tolentino is famous and successful because, against all odds, she found an eager market for her work. Put bluntly: who the fuck can afford the ambition of 2010 Jia Tolentino? Literally imagine a 28-year-old sitting down and writing, like, The Corrections. Are you kidding me? This is why we’ve ended up with sheepish, self-effacing little novels like Early Work, which are alternately admired for their modesty and ignored because what’s the point.

deBoer continues:

The past 25 years or so of media and literary culture has ruthlessly undercut the idea that writers should be proud of writing, ambition equated simplistically with pretension by endless Spy magazine clones, spurred on initially by resentful younger writers watching people like Tom Wolfe getting comped at the Four Seasons while the basic economics of books and magazines crumbled. But that was a long time ago. Perhaps those who witnessed the Tina Brown excess of an earlier era can be forgiven for this visceral hatred of writerly self-importance, but I’m never sure what to think when I see it in young Millennials. There are now no big timers whose condition you should envy, not really. So why bother? Why ironize and undermine that which has already been ironized and undermined beyond rescue? It seems, at times, like the literary internet will never leave the comments section of Gawker circa 2009.

I think the attitude he’s describing is the logical conclusion of Gawker-era snark, so it makes sense to me. The Gawker commentariat was mad that untalented hacks were clinging to diminishing media jobs. Today, there are even fewer media gigs to go around, and writing as a profession pays worse, but every time you open The New York Times you’re faced with a reminder that Thomas Friedman still pulls a salary. Why wouldn’t everybody spend all day sniping at David Brooks on Twitter? Not only is he a buffoon, he’s proof positive that meritocracy is a sham.

It’s easy to wax nostalgic for a time when people wrote just to write, but I’m not sure it ever existed. Editors and publishers once held the keys to audiences; today, platforms do. It used to be that if you wrote a great book (or story, or essay, or column) it paid off—perhaps not right away, but there were staff jobs and publishing deals and tenured professorships to be had. deBoer’s correct that those financial incentives don’t exist anymore, but the result is a radical diminution of literature within American culture. There’s hardly any apparatus by which a young writer can get an ambitious book into readers’ hands. Money’s been off the table for a while, and now even clout is virtually unattainable. Imagine a person who, at a time when writing pays nothing and affords zero cultural cachet, elects to do it anyway. Jia Tolentino agonizes over this every time she sits down to write: it takes a special type of sociopath.

There’s an old tweet I can’t find about how if Bob Costas were born in the ’80s he’d work at the mall and have a podcast no one listened to. The joke is self-explanatory: Costas is such a categorical boob, his success so obviously circumstantial, the only explanation is that no one ever told him no when he decided his gutless opinions deserved an audience. Don DeLillo is not, for the record, such a hack, but he supported a family (in Bronxville!) working odd jobs until he was 50 and then, whammo, he published White Noise. Does that sound like a realistic path to follow? The money moved on, then the culture moved on, and now everyone has a podcast.

Do you know what happens to people with ambition? They go into debt paying for useless MFAs, then pass their golden years working as baristas and copywriters and SAT tutors for children of hedge fund managers. These material conditions have reduced writing to a hobby. Writing a novel will not pay your bills or cultivate a following, but posting might. Jia Tolentino posted her way into a job at The New Yorker, which, from where I’m sitting, is the only path left, even for someone as remarkable as she. And she feels lousy about it! You can’t ask people to be ambitious, dick-swinging writers and then call them vain for trying.

If Tolentino is one of the most accomplished writers of her generation, she is also—and she’d be the first to admit it—hopelessly of her generation. She’s an empathic critic and perceptive journalist who loves unscripted television and Britney Spears. She’s ingenious but rarely transcendent. This, I think, is why Trick Mirror was met with such rapturous acclaim. It was a celebration that Jia Tolentino, vanguard of the new literary vogue, was one of our own, a person who’d rather write navel-gazing essays than highfalutin systems novels.

First-person time. I’ve been writing semi-seriously for a few years now, and I’m not very good at it. This isn’t cheeky false humility like deBoer accuses Tolentino of: I read enough to know quality writing when I see it. I don’t think I have a great book in me, but there’s probably a passable one that could have been quietly published in the ’80s, back when being an anonymous white guy with a pseudo-fancy bachelor’s degree was enough. If my rent weren’t $2,500 and healthcare were considered a human right, I might be able to hone my plotting and character development in service of a methodical, wryly humorous narrative. I’d likely add some superfluous psychosexual trauma and white-ethnic identity to make it all seem more profound than it actually was. Perhaps Freddie deBoer would like it. Thank God I’ll never do it.

Here’s the thing: ambition, like writing itself, is fucking embarrassing. Ambition is a synonym for sniffing your own farts and validating your own opinions. No one remembers this, but five years ago every literary novel was a coming-of-age ensemble story about four college friends — an artist, an architect, a sensitive lawyer, and a conflicted banker — taking on New York City and struggling to balance authenticity and passion with their blooming careers. I don’t know if deBoer is a big Jeffrey Eugenides fan, but this is what passed for literary ambition in the Obama years. These books were bad, but mostly they were tone-deaf. People are dying! No one gives a shit about your Dartmouth love triangle.

If the decline in material conditions has resulted in a paucity of writing opportunities, what remains should be considered essential. Trick Mirror may not have been a very difficult stretch for Jia Tolentino, but at the time it seemed important. (Fucking Jeffrey Eugenides certainly couldn’t have written it!) In this context, Tolentino is essential because of the perspective she applies to current events. This market will not produce a Ford or an Exley—both of whom were, by the old standard, pretty ambitious—because those perspectives are not pertinent to the world burning around us. Tolentino’s ambition, to that end, is immaterial.

There’s a Jezebel post from 2015 titled “Who You Write For Is Who You Love,” a nice little On Writing-style blog in which Tolentino concludes:

Who do you write for? Both to my gain and my detriment, my only answer is myself […] In life and in writing, it’s immensely seductive to feel personally responsible to an audience. But in life we’re responsible only to the people who love us — and in writing, to the people we choose to be responsible to, which is one way to figure out who we love.

I’d argue Tolentino’s corpus suggests she’s in fact writing for any number of different people, but regardless, I struggle with this. I love the maximalist, masculine writing of William Kennedy, Edwin O’Connor, and Robert Penn Warren. (Fuck it, I think Infinite Jest is a heartbreaking work of staggering genius.) Their work makes me feel seen. I also think there’s a type of writing that exists on a higher plane—writing that works to inform and inspire rather than corroborate, writing that provokes compassion and equity. This is the kind of work Tolentino regularly produces, and if that makes her unambitious, more power to her. She scrapped the Kyrgyzstan novel because she realized it wasn’t her story to tell, and that it might embarrass her later. I disagree with deBoer’s assertion that there is “inherent nobility in the work of being a writer.” Words have no inherent value just because they’re words.

deBoer implores writers to think about what kind of writer they want to be, because “no one else can take us seriously for us.” Maybe this is one of those Gen X/Millennial divides, but that’s totally fine by me. There’s probably a reason no one writes books like Roth and Wolfe anymore: people older than us read that shit and took it to heart, and now look. No one needs a book about why I’m the way I am — for all my endless complaining, I’m fine. deBoer thinks we can finally sit and write our big books now that the stakes have been lowered, when the reality is there aren’t any stakes at all. I wish people had more shame.

Like a lot of folks exhausted from a decade on Twitter, I’ve been trying to post less and generally succeeding. Part of it is the economics behind it: it’s true that Twitter makes us perform free labor in service of a company’s shareholders. But it’s more the fact that it’s needy and pathetic. The problem with Twitter is the problem with Substack is the problem with Andrew Martin books — the assholes on these platforms are just writing too fucking much, to the point where it’s masturbatory and offensive and sucks all the air out of the room. I’ll close by quoting Raymond Carver, perhaps the best counterargument to the big, wordy books deBoer treasures: Will You Please Be Quiet, Please?



Pete Tosiello

writer, on good days. NYC. @tosiello