Part one is here.
1.
There is a lot of good writing and publishing advice on Substack. I like a lot of it.
Any advice I can offer in regards to Literary World is cautionary-tale advice. Things I've learned firsthand, the hard way.
I often wish I had intuitively known the right thing to do when I was young, but I have only learned through trial and error and failure.
The thing you need to understand is that no one knows your life better than you, and no one can help you.
I am not a successful writer.
Among the New York literary milieu I came up with, success-wise, I’d say I am deep in the lower third tier.
Most of those in my cohort have published nonfiction books or mid-range novels, teach writing or journalism at universities, do book-to-film, or edit cool magazines and journals; and many of them are married and/or have kids on top of that.
I have not met the mile markers of a successful life. No kids, no book, no wife—not to say that those things haven’t been on the table or won’t be again, but I didn’t take the reins. I’m holding out for the right lifelong commitments (that’s the lie I tell myself.)
I’ve made my decisions, others made their decisions, we all make our decisions (or we avoid making decisions and have them made for us) and then the factors like luck, chance, timing and skill play their part.
As
put it in an essay I liked a lot: "I identify a lot with Brad Pitt’s character in Moneyball: the highly-touted baseball prospect who turns out to be a dud."As Rachel Cusk noted in Transit, creative problems are inseparable from problems of living.
That is to say: “creative problems” are just personal problems.
It should go without saying that the most important part of any creative endeavor is Doing The Work. No amount of getting to know people or putting yourself out there or hanging out can fix a chronic un-doneness of work.
But what exactly is The Work?
There is The Work that the people want, the work that “you want”, The Work that the gatekeepers want, there is The Work of dreams that is not grounded in practical realities (as Steve Jobs famously said: "real artists ship" ie. even if it's not done, just get it out.)
Writing is communication, and communicating means sharing. I can say I’ve worked hard, but not smart—if you write hundreds of thousands of words but don’t share or don’t publish them, if they turn inward like a nautilus shell, is that work? Perfectionism or obsessiveness is just another way of not-finishing and not communicating.
Am I bitter and mad at myself? Sometimes. Sometimes I seethe.
Sometimes I play the what-if game:
Ohhhhh If I had only done this at that time or not done that, or met this person or that person, or gone here or done that…Can I still turn things around? Yes I can! No I can’t! Oh, this is so navel-gazing, oh I hate myself for being so navel-gazing…
Sometimes I’m filled with deep gratitude for my life experiences. In the end, most things that happen are either your own fault or bad luck. That’s the big-hearted, self-reflective, tired-but-happy-eyes take. But I dunno, maybe it’s bullshit. What about the role of others, what about revenge, don’t I also want the barbarians to storm the gates?
I have to say I feel much more in common with this rising tide of weirdo dissident lit people than the two previous generations. I felt deeply alienated from the popular lit of the 2010s.
At the same time, I can see most of these rising writers are driven almost entirely by petty resentments, by being outsiders, by their little literary populist uprising against gatekeepers.
I don’t believe the platitudes about independence or whatever for a minute, if the big dawgs reached their hand down with a treat and validation, almost all of them would take it. I see them as talented minor-leaguers down in Tampa, each hoping that their talent will be discovered and validated.
2.
I met Don Delillo's editor once at a party. He also discovered David Foster Wallace, but he didn’t talk about him, he talked about Don Delillo. I’m not sure if I asked or he offered, but maybe he sensed I was lost, so he hammered home a piece of advice that has stuck with me. He said1:
Don Delillo never wrote book reviews.
He didn’t do opinion pieces or takedowns.
He didn’t engage in bullshit culture debates like Susan Sontag or William H. Gass, or write criticism.
He just worked on his novels. That was what he did.
I felt this. It seemed so dignified, so proper. To live out away from it all, sauntering down to the rural PO Box once a week like Cormac McCarthy and Henry Miller (in Big Sur and Oranges of Hieronymus Bosch) to send off manuscripts and answer letters from adoring agents and editors who were always saying things like "we sold the rights!" and “they’re eating it up like Thanksgiving dinner.”
At the same time, his advice felt outdated, from the former world. I had just gotten to New York and gotten my foot in the door, that’s how I was meeting people like him—what was I gonna do, ditch it all immediately and run off and become a gentleman-farmer at 24?
His advice, I think, boiled down to “don’t be a literary person.” Or maybe, “don’t be a person-of-letters—a New York literary world gadfly—if you wanna write novels.”
Later, I saw a bit more what he meant.
When you meet people who have published books, there are usually two kinds—ones that show up in New York to do some business and have a wonderful kind of “aw shucks, this city crazy” naivete—they’ve been living entirely separate lives from the publishing organism, and you know, writing their books.2
Then there are the others, the literary people—they’ve hung around long enough and know enough people and got the MFA and published here and there, which apparently entitles you to get a job teaching writing. They have paid their dues as an editor for some small journal, they go to AWP every year, all their friends are literary people, they review books positively so that when they publish their book they’ll get a nice review. Then they are a “person of letters” and then they’ve written a book.
3.
Though I heard it and it penetrated my soul, I didn't follow the editor’s advice at all. I felt like it was meant for other people.
I knew I had to get some articles out there (they were called “clips” at the time), so I did a takedown of Christopher Hitchens. My argument basically boiled down to—Hitchens used to be a real communist and now he’s not. (God forbid anyone ever change their views!)
I found out Christopher Hitchens had cancer shortly after my very-mean takedown got published.
The editors of the site I wrote it for were happy with the numbers and wanted more numbers and wanted me to go "confront" Christopher Hitchens at a public event. I said hell no, I'm not doing that. It felt dirty. I felt like the whole thing had been a poor use of my time, and I felt bad for hating a person that people clearly loved. (I also received random hate letters for years, from his devoted fans.)
Over endless beers, I gossiped and talked shop with the boys, the Aspiring Literary Journalists. I loved drinking beer and talking shit with the boys in Greenpoint. It was romantic. But I was also frittering away my agent friend's time about a non-fiction, reported book that I said I was going to write a proposal for—a book about American utopias, the Oneidas and the Shakers and the Free-Love Midwestern Commune people.
I did endless research for this project, reading the dullest academic books imaginable cover-to-cover, and in the end, it was clear to me (even though I continued lying to myself that it was "right up my alley") that I didn't want to do it. I did not find “communes” romantic, I found them sad and depressing. By that point in my life I had been through enough squats and "temporary autonomous zones" and punk houses to know there was no such thing as utopia, there were just people destroying each other in new and innovative ways.
I then decided to send out my "novel" (which was just a repackaging of my punk zines, presented as fiction) to editors and agents. Why not me? I thought. If Keith Gessen and Benjamin Kunkel were able to publish navel-gazey, rambly first-person novels, why couldn’t I?
The reasons were obvious. Gessen and Kunkel were beloved editors of an important literary journal and I was not.
I only sent the manuscript to a couple of people and when it was greeted with what I imagined to be befuddled silence, I felt ashamed and embarrassed.
First off, you are not supposed to send your manuscript to editors, you send query letters to agents. I did not know how things were done and did not do my own research to find out. I could have found out, I had the access, but I never bothered.
I still had the zine, DIY mindset. If you want to do something do it; just call people up, ask to play the show.
I did not persevere and send my manuscript down the line to other agents or editors. No, I withdrew and decided it was not good and that I could do better, and I honestly didn't like the idea of just repackaging something I had already done in one world for another world. It reminded me of the zine-writer Dishwasher—he wrote a popular zine that people liked about being a dishwasher, and out of the hundreds of talented zine writers, for some reason he got a major label debut. They put out a book about his life as a... dishwasher. Typical Book-Pitch Mindset. I flipped through it once. It was boring. And I think it sold poorly.
I got asked to report on things, I was given shots by a few big editors and wrote book reviews for small journals—some of them got published, some got "killed" with a “kill fee” in the parlance of the industry, and that was always crushing. They never told you why a piece got killed; all your work, all your effort, it just died on the vine.
I decided I had to further sublimate my grand ambitions and eat shit for a while longer.
But I still found myself thinking about the editor’s advice. I thought of it every time I spent weeks writing a “take” or months devouring six books to write a 3,000-word book review. Or did months of boring research and dozens of interviews for a piece of reportage; it bothered me when, years later, I had still failed to establish a “beat” or “subject expertise.” And it bothers me even now as I publish these little memoir-essays on Substack.
4.
The Very Reasonable Idea is that you’re just not ready to do what needs to be done yet. But if you just write enough book reviews or takes or takedowns, or edit or fact-check long enough, then one day—after you’ve paid your dues—you’ll get to do something real.
This idea is based on delusional notions of infinite time and infinite ability and infinite will. It doesn’t account for the possibility that you might be used up.
The problem is that sometimes you never get there.
You can get stuck inside the walls of the house.
You can keep cranking stuff out, but none of it leads to anything.
You can go for decades in the wrong direction and live the wrong life. (read Michael Rance’s essay.)
You can pour your blood and sweat into writing for magazines and websites and little journals and then one day when you go to their websites, you see they’re defunct, and your heart breaks a little bit (I’m looking at you, Al Jazeera America, Vice).
The self-help people say: strivers and aspirers and perfectionists are driven by fear. Doers just do and accept the consequences. They follow through even when their heart’s no longer in it.
But therein lies the rub—there are so many different kinds of doing!
Doing that leads you upward and outward. And doing that leads you deeper into the fog and muck of confusion.
Take the great James Agee—Let Us Now Praise Famous Men, his half-finished novel Death in the Family—published from drafts after he died.
In life, he wrote movie reviews. (I think he probably took prescription speed to write the movie reviews.) He died in a New York cab from a heart attack at 45.
I remember
and I once talking about the well-respected longform magazine reporter and essayist Matt Power, a person I liked and admired, who was a kind of model for me.Christian said, “He’s doing great. All he needs to do now is buckle down and write a book!”
He didn’t get around to it. He died while on an assignment for Men’s Journal, in some godforsaken place, from dehydration.
And those are just two people that are remembered.
I have always had a soft spot for the failures and the forgotten and the obscure. Those who, for whatever reason, couldn’t make it, and disappeared, half-remembered. You could fill an encyclopedia with them. An encyclopedia of forgotten journalists and critics. I actually thought about undertaking this as a real project at one point, but it was too overwhelming.
The big danger of romanticizing failures is that you subconsciously or semi-consciously drift towards it in your own life.
5.
I will now recount a few more mistakes I made professionally—things that still make me cringe and think “Oh my god, what was I thinking.” My advice, aspiring writers of Substack, is don’t be like me. I was warbling between brash, unearned self-confidence and a deep sense of inferiority:
—I published one article in The New York Times and all of a sudden felt like I was hot shit. I never wrote for The New York Times again.
—I went to an interview for an assistant editor job at a Big Five publisher. I think a friend of mine helped me get the interview. In the glass-walled office room during the interview, I proceeded to talk shit about most of what they published.
—I wouldn’t say I was an enfant terrible. That implies a big personality and lots of dramatic public scenes. But I talked a lot of shit about people, and it got around, and then people talked shit about me.
—I was presumptuous and mingling at a fancy Eyes Wide Shut-feeling Central Park West party and "introduced" some big time editor to some other Ivy League editors—they all knew each other already, of course. The magazine editor looked at me like, "I can’t believe the gall of this kid!”
—I proposed to the publisher and president of Harper's that I could go through the archives and select and edit a book of the best Harper’s pieces of all-time. Again, I was an intern. You have to earn it, baby.
—When a person who later became a big-time New York Times Magazine editor asked me what I thought of his big recent piece, I gave him my honest opinion (always a bad idea). I think it sounded like I was negging him. I was still naive enough to believe in honest and open dialogue, I thought people wanted honest opinions.
Amazingly, he later asked me to write something for another big magazine he edited for, about online dating—he wanted me to do a “submersion journalism” first person article about online dating. I had a girlfriend at the time, so I never answered or followed up (it was actually a great opportunity being handed to me on a platter, I should have done it just for the clip in that magazine).
—I wrote emails with bad grammar and very little punctuation and lowercase sentences and exclamation points and then at the end signed off in all capital letters—AARON like the email was a fucking piece of art written by Christo or Picasso.
That's all I can think of for now.
6.
There is a little koan in Nelson Algren’s wonderful and bitter 1953 book, Nonconformity:
The less [a writer] sees of other writers the more of a writer he will ultimately become. When he sees scarcely anyone except other writers, he is ready for New York. If he is already there, he will go to work for Fleur Cowles. (the editor of Look and Flair magazines, the fancy, vapid Condé Nast Travelers of their time)
Look Magazine and Fleur Cowles was, for me, the fact-checking department of GQ magazine, at the Condé Nast building.
Before getting a job there, I had never picked up a copy of GQ magazine in my life.
My prejudice was that only gay men or insecure urbane straight men cared deeply about mens' fashion.
But GQ’s reporting section is highly respected, they have a big budget for reporters and good editors with great instincts.
I was grateful for the work, and the camaraderie. The hours were flexible, the pay was good, the company was good, lunch was delivery food from fancy Times Square places—what more could I have asked for?
So why did it feel like all the fact-checkers were so on-edge and eager to get out of there?
I suppose it's because, while we were very comfortable, it was also a kind of holding pen for developing talent. Most people didn’t want to fact-check forever. It was a stepping stone in a longer trajectory.
I don't know any sport well enough to do an analogy, but I imagine that for many fact-checkers, it was like getting a great job as a communications coordinator in the front office when what you really wanted to do was to be a player (writer) or a coach (editor.)
Some of my colleagues immediately made it out, skyrocketing into the literary stratosphere with a story or reported piece in The New Yorker (the biggest break that could possibly come to a person.)
Some of them grinded their way out, a small piece here, a small piece there, finally a big piece, etc.
Some used the time to work on a book proposal, put out a non-fic book, but kept the job because the advance was not a mega-advance.
Some had no ambitions at all as writers or editors, they wanted to be musicians or designers or just live their life comfortably, and they seemed the happiest.
I’m paraphrasing a very brief conversation from fifteen years ago, so I hope this is reasonably accurate.
New Yorkers love a charming outsider. There is something so nice about someone who comes to New York but is not OF New York. People can sniff out their fundamental separateness, otherworldliness, and they are somehow sweeter, more open. The charming-outsider-in-the-big-city narrative is probably best depicted in the John Waters film Pecker—a life-loving photographer from a vibrant working-class community in Baltimore is snatched up and drafted into a commoditized art scene in New York. But the reality of publishing is often more like the great movie Julie & Julia—a blogger with an editor boyfriend consciously undertakes a project that is specifically framed to snag a big book deal; there are struggles and setbacks, the couple fights and almost breaks up, but then the glowing review in the Times redeems all, widespread acclaim follows.
Aaron,
This is an excellent piece. You're a good writer. It's really hard to write with this kind of honesty and I really appreciate your sharing it here.
A few thoughts:
- You tend to write as if you're at the end of something, like it didn't work out for you. My suspicion is that you're actually at the beginning of your writing life.
- I've had a lot of the same kinds of thoughts that you've had, about these hard-and-fixed literary statuses ("deep in the lower third tier," that kind of thing), and I know how immutable all that can seem, but there's a point where if you're really putting a lot of time into writing and enjoying the writing, that goes away - and it's very interesting how it goes away. In the end, writing is interesting. The politics of writing is not.
- I know a lot of the kinds of people you seem to know and, in the end, they're lightweights with warped values. Yes, they manage to maneuver their way through the system, and they get opportunities and they get accolades and they may even be remembered (because the gatekeepers can also control posterity), but their books are bad....and necessarily bad because they're based in cowardice, because they didn't do the actual Thing of accessing and trusting the deep part of themselves. Good readers can always tell. And I've read enough of what's come out of this era of literary work to see how little any of it is based in actual interest or desire.
- When you look back at your various career flubs, what I think you'll at some point discover is that it likely was something in your system letting you know that that wasn't really for you, that that wasn't the right path for your spirit. Hopefully, the real path is something that allows you to write with all of yourself and all of your courage.
- I know you're a bit skeptical of Substack (as in the paragraph that you deleted lol!). I would say that the actual Substack platform isn't so important - it's just what happens to be available to writers at this moment in time. The important point is the ability to write infinitely and also to reach actual readers - although without necessarily passing through the gates of status to do so. My favorite analogy about writing is that it's like sea travel. Lit mags, reviews, scenes, status, readers for that matter are all just the coast. The actual Thing is when you set your sails and you're out in the deep sea. You may well never reach the other side, you may well never see land again, but that's not so important. What's important is doing the Thing. And, in the end, that's what everybody, at a deep intuitive level, respects.
All best,
Sam
“By that point in my life I had been through enough squats and "temporary autonomous zones" and punk houses to know there was no such thing as utopia, there were just people destroying each other in new and innovative ways.” - This is a hell of a line!