It was Christmas Eve 2016. I’d just moved to NYC in September and by December, I could be honest with myself about how things didn’t seem to be going to plan. Case in point: there I was, on Christmas Eve, nowhere to go and nothing to do except buy a large cheese pizza, a 4-pack of Yuengling tall boys, and a bag of chips to get me through tonight and Christmas Day.
“Worst Christmas Ever chugs along,” I’d written in my journal on Dec. 11, 2016. It’s not as if I’d expected a welcome parade when I arrived. But my presence barely registered with anybody at all, even with the college friends in town. But why should it? It’d been over 5 years since we’d all been undergrads. I also didn’t have a lot of law school friends and big law firms aren’t conducive for socializing. I was trying to meet more writerly friends, but nothing had come of it yet.1 So dating apps provided the bulk of my social life. Some of my favourite dating memories are from that time.
Actually, late on Christmas Eve, a woman I’d gone on a date with a couple of months ago texted me. I was surprised to hear from her because we’d had a nice first date, until I tried to kiss her, at which point she leaned away from me as if she were doing the limbo. I’d gotten the message and awkwardly walked her back to her subway station. But it turned out I must’ve misread the situation! I excitedly invited her over for hot cocoa and Christmas TV specials. We did kiss this time and it ended up being a sweet, rescued night.
So the night could’ve been a lot worse. But it was still pretty sad. However, I thought of it more as funny. First Christmas in a big city, so what could one expect? So I decided to take the photo below with the utmost confidence that it’d be a comical memento by next year, and a good reminder of how far I would have come along in establishing myself. As Christmas Eve was turning into Christmas, when I was alone again, I went to a local dive bar, The Cherry Tavern, to drink whisky at the bar by myself. Kind of like George Bailey as he contemplates suicide in It’s A Wonderful Life. If you’re going to be pathetic, might as well make it as cinematic as possible.
We hear and read all the time now about how we’re in an unprecedented age of loneliness, especially as you get older, and especially in this era of digital atomization. Sometimes with some smugness, I think of myself as a counterpoint to that claim. It was only after moving to NYC in my late 20s that I really started to make more of the friends I truly felt connected with. Why is it so hard for other people?
But then, I think of my first Christmas here in NYC and see a downward path I most likely would’ve followed had I not started writing online. I’d been trying and failing to find a like-minded circle of friends. I’d only been in my first apartment in NYC for 1 month before my roommate asked me to move out because he wasn’t “feeling it.” With my next roommate, I had a great interview and I thought we might become friends. But that didn’t pan out. I’d go to literary readings and try to meet people there, or I’d chat up the baristas at the café where I liked to write to try to be a known regular, but to no avail. It was 9 months of this kind of loneliness.
Things began to change around May 2017, I met the friends with whom I’d start a magazine (Plan A) and podcast and that was when I actually began to have a real social life. Many of my closest friends today were those I met through my writings or podcasts. And since starting my Substack, I’ve recaptured that feeling and energy that I had back then during Plan A’s heyday. I’ve met a lot of good people here, some of whom have also written about the joys of writing on the internet2 or, as I will do further below, about Substack discourse.3
A wise ex-girlfriend once told me that I hated everything about myself except my writing. While I do have more self-esteem than that, she was onto something in that my writing is what I value most in myself. It’s no coincidence that only by sharing such writing have I been able to meet the friends I’ve wanted all my life. I’ve met many people who want to write but are afraid they have nothing to say and that writing would just be an exercise in narcissism. The thing is writing is indeed narcissistic. But it’s also a generous narcissism, to expose some part of you in hopes that total strangers will connect with what you’ve written.
I’m not someone who’s very open about my feelings, at least in person. But there’s also nearly a decade’s worth of my writing on the internet. When I’m dating someone new, I wonder when to tell her about these writings. On one hand, my writing is what I’m most proud of, so I want to share that with people I like. But then she’ll know so much more about me than vice versa. Isn’t that kind of asymmetric information unfair? But if love is about appreciating and understanding the most personal and even very dark parts of each other, what am I being afraid of?
It may be a harsh truth, but people don’t want to get to know you unless you have something to offer. For a lucky few, they may be so wealthy or so attractive or so charming that they draw people to them with minimal effort. For the rest of us, what do we bring to the table? It wasn’t if I’d only started writing in 2017, but prior efforts were very private (my first novel) or semi-private (like a blog that only my law school classmates read). But what widespread good does that kind of hidden writing do? In a superficial society with short attention spans, where people nevertheless do crave to experience authenticity, you are doing something much-needed if you not only write honestly and introspectively, but are generous enough to share that. To hell with the risks of criticism or ridicule.
Recently, I had dinner with my friend Jackie, who told me about some friends of hers who had secret blogs. I said that deep down, they wanted to be read. Otherwise, why put it online when you could hide it in a notebook or app? I hope they publicize their writings one day. I’m sympathetic to arguments that too many writers and too much writing can result in homogenization.4 But people’s writing can always improve and we all have to start from somewhere.
A few weeks ago, I went to Red Hook to see a literary panel that featured Lauren Oyler and Brandon Taylor, where they discussed the rising popularity of take-down book reviews. The topic of Substack also came up, and Oyler and Taylor’s disdain for it was palpable. Oyler dismissed it as a “tech bro” way to foster a literary culture. But given that Amazon and TikTok rule publishing these days, what part of literary culture isn’t greatly influenced by tech? Taylor didn’t say much about Substack, but he recently announced he’s going to leave.
For some established stars of the literary industry, as talented as they may be, Substack is troublesome because it muddies the hierarchy too much. These stars are the precious few winners of a grueling game and their reward was to be exalted status and access to elite publications like The Paris Review. They may have and use other social media like Twitter or Instagram, but there, we could only interact with them using degraded forms of literary expression, like tweets or photos or comments. But long-form writing—the most prestigious form of writing—remained the exclusive domain of the winners. Sure, anyone could start a Wordpress, but nobody would read it.
Some very popular writers on Substack, like Clara5, seem to have similar thoughts:
On Substack, there’s no superficial or functional difference between a 4000-word essay by a literary star vs. one written by a total nobody. And the total nobody’s piece might end up being more popular. The orange star lacks even a fraction of the social cachet that the Twitter blue check used to hold, further flattening the playing field in terms of status.
I get that Substack, or at least the parts I’m familiar with, can sometimes seem like a really irritating AP Lit class. But given how much more brutal other social media platforms are, shouldn’t that be a plus in Substack’s favour? Unless, of course, what makes it unbearable is precisely because it’s full of those supposedly less-gifted bookworms that ought to have been weeded out by the game long ago. For whatever flaws Substack might have, it has brought writers of all sorts together. I find it very suspicious when there are writers who are unhappy about that.
When I was younger, like in my 20s, I did dream of big literary success as the most important thing. As I finished the first draft of my novel in the months leading up to law school, I fantasized about the book quickly getting published and becoming such a bestseller that I could drop out. Now, I have more tempered dreams. I still want to get books published, and if they do well, that’d be great. But more importantly, through those books, I want to meet and connect with people I wouldn’t have otherwise. I figure I’ll be working a day job for the foreseeable future (it’s nice not having to worry too much about money). I don’t plan on ever charging for my Substack, mainly because I don’t want that kind of financial obligation to any paid subscribers.
What I’m mainly looking for is community. Quality friends. And quality enemies, too. Because what else is there? Even the top-level money in writing is not that great. Some friends and I were talking about various authors’ big advances for their books, and even the notable ones aren’t much more than what some middling i-banker makes every single year. We’re not talking about Ohtani-level contracts here.
One of my favourite Substack pieces is Freddie deBoer’s The Party’s Over,6 which I first read sometime in 2022. I was feeling adrift as a writer and found some sour-grapes comfort in the essay:
What Substack and Patreon and assorted other forms of independent publishing can’t do, though, and aren’t attempting to, is to congeal into a community, which is what people really want. Not just a job that pays the bills, but a social world. The kind of social world that was once such an indelible part of media. I’m glad you moved to a cheaper town and I’m glad you got that day job. I’m afraid in adult life there aren’t any parties that don’t involve pinatas and shitty pizza, though. You’ve heard it from me before - an aging workforce, insane rents in major cities, and stubbornly low wages ensures diaspora makes more and more sense to people who are brave enough to keep trying to do this. Then Covid comes and whatever tether there might have been to some such thing as a “scene” is gone. It won’t come back, not in anything like the form it once existed. Is that worth mourning? For me, no. But for others, sure, and they are entitled to feel a little cheated.
This passage was soothing because if I was feeling out on an island by myself, then so was everybody else. At least I wasn’t missing out on anything. But a couple of years later, I think deBoer was wrong. Or he was right at the time, but what he said is no longer correct. It could very well be true that what literary communities we have today pale in comparison to what existed then. But it’s at least a community, and since I was never part of the Millennial media glory days of the 2010s, it’s all I’ve known.
Not everyone wants to write, and it is a bit of that writer’s self-centeredness to think that everybody ought to want what he wants. But what’s always drawn me to writing is that it’s such an old and basic skill that we all learn from a young age. If we are indeed living in uniquely disconnected times, why shouldn’t we use such a skill to try to connect with others? To write is to light a beacon, and so often, we are little boats, drifting on the vast waters in the dark.
Merry Christmas, everyone!
The Party’s Over by Freddie deBoer
Nice article, Chris. This stuck out to me: "What I’m mainly looking for is community. Quality friends. And quality enemies, too. Because what else is there?" And your acknowledgement of the monetary reality has been something that I've always accepted and never tried to consider in my own time. The "fame", the recognition, the communication between others who loved what you wrote and want to discuss it with you? Yes, of course. Slightly different from your direct desire for community, but shaded in the same color. That is to say, in my mind, we both desire the same thing from people.
When I tell people I'd happily spend $1000 (to pick a number) on formatting and cover art for a novel I wrote, I inevitably get the comment "But how are you going to make that money back on sales?" And the answer is: I don't expect to. I want to make something that I'm proud of, that I can share, and that will always be mine. When I'm very old and looking at my shelf, I'll see books that I worked hard on years ago that still look just as I desired them to look when I wrote it. You can't put a price on that and you can't expect money back from that. It's not about the money. It's about the craft, the art. That matters more than anything else.
In any case, cheers from me. This topic has been on my mind a bit recently, likely because of the holiday season. Thanks for writing it.
"A wise ex-girlfriend once told me that I hated everything about myself except my writing. While I do have more self-esteem than that, she was onto something in that my writing is what I value most in myself. It’s no coincidence that only by sharing such writing have I been able to meet the friends I’ve wanted all my life."
I relate to this 110%. I came to NYC in 2019 and online dating supplied friendships until the 12-step recovery world stepped in (I'm 14 years sober). It's a tough racket, especially in Manhattan.