one of the weird paradoxes of sending newsletters is that not sending newsletters for a long time will not really affect your subscriber base, but if and when you start sending them again, people will unsubscribe, and the more newsletters you send to them, the more people will unsubscribe, because, it turns out, most people do not actually want more newsletters (or at least not more newsletters from me, but i understand this to be a more common phenomenon).

i mentioned the shedding to Deborah and she said something that i also heard from a kind reader long ago during my paid newsletter experiment in the summer of [croaking old man voice] 2012, when i charged $2.22 a month for (near) daily emails with typewritten attachments, as described in this old Awl newsletter:

which was that maybe it would be better for me and better for my audience if i wrote and sent emails less frequently. i think that's 100% true and also it's just kind incompatible with how my process, as far as i have a process, has ever worked! every time i stop writing as a regular practice, starting it again becomes harder to do every day, so i have to be regular at doing it if i want to do it at all. this is paired with the fact as someone who started from a position of instantly publishing myself whenever i wanted, i have no patience for delayed gratification! even if the gratification, in this case, is mostly just people unsubscribing.

Deborah just built a new personal website with an archive of all her amazing comics and started up a newsletter on Substack. they both make me so happy and you have to check them out!!!

• Deborah's newsletter
• Deborah's art site (start here and swipe (mobile) or use arrow keys (desktop) to seamlessly read her comics from the very beginning)

the other day she and i were taking a long walk and chatting about it and she revealed that she was planning to add a soft paywall to her newsletter. when she mentioned it, i had a too-strong reflexive negative reaction to this choice and started, as usual, running my mouth, saying that i just didn't understand why she would start with a paywall instead of building a larger audience with free content first? we worked through it in the moment but this made her feel judged: as her therapist put it later, "to you, it sounded like he was saying your writing is not worth the money." i eventually realized that a) that there was no need for me to offer this unsolicited advice (a fact i keep trying to learn: there really basically never is!*), and also b) i have never actually been that successful at building, growing, and sustaining an audience for my creative work, so what do i even fucking know in order to give someone advice!

in 2012, a month into doing my paid newsletter experiment, aping the then-fresh language of Patreon, i sent a "backer update" talking about how the experiment was going, which from my perspective was "not as good as i'd hoped". you can read the email in full here

as mentioned in my stories newsletter earlier this week, a few years before the paid newsletter experiment, i got on Tumblr. i got on Tumblr as someone who thought that Tumblr was the end of blogging/writing/thought in a kind of Idiocracy type way. in particular, i had a level of completely disproportionate incandescent rage about the existence of Jessica Grose and Doree Shafrir's "Postcards from Yo Momma" blog-to-book deal to the point where i was in blog comments basically doing Peter Thiel calling Greta Thunberg the Antichrist except my Antichrist was a user-generated content gift book of nice messages people's mothers sent them to be sold from the book table in Urban Outfitters. (i was also having my first real nervous breakdown at the time, which may have contributed to how excessive this reaction to usage of a microblogging platform was!)

but as much as i thought Tumblr was horrible, i also felt, especially because of said first nervous breakdown, that i just couldn't keep doing the thing i was doing at the time (manically write obscure many thousand word posts in all lowercase in a tiny font on a Wordpress blog that would only get read by more than a handful of people if they were good enough to get picked up by the Awl) and it seemed like the energy of the zeitgeist had shifted to Tumblr and i wanted to be part of the energy, to have a community, so i went there. and it turned out to be my happiest time on the internet.

i think maybe the most effective gesture i ever did myself for growing my audience was when i first signed up for Tumblr. most of the Tumblr layouts had lists in the sidebar of everyone who an account was following and/or followed by. one of the few Tumblrs i read at the time was agrammar, which belonged to the music critic Nitsuh Abebe. He seemed like a smart person who would have smart people following him, not these other illiterate idiots, so in order to bootstrap myself onto the platform, I just opened a new tab with every one of his subscribers' tumblrs and if any of them seemed relatively interesting, i followed them and started liking their posts if they were likable. combined with clutch shares and praise from important writers i respected and a regular posting cadence enabled by being unemployed and living wiht my parents, i really felt like i was growing my audience. as a deeply anxious person who has always felt discomfort with self-promotion, this flywheel, which just required me to consume content and click a heart button, was perfect.

that was such a smaller, simpler internet, though (and as the hero image of this newsletter issue shows, it's not like i still didn't feel status anxiety at the time). it just seems like these kind of plays just don't really work anymore: the scale is different in kind rather than in degree. there are so many interesting people doing and saying and writing interesting things all around the world. that's wonderful and horrible at the same time: wonderful because "look at all this cool stuff!!" and horrible because there's so much cool stuff that nobody has time to look at much of it (especially while trying to get people to look at theirs). i feel very lucky that i still have you all reading these emails of mine after so many years and that, in periods like this when i want to write, i can write to you instead of having to start finding readers from scratch.

i remember the first time i went over to Deborah's apartment when we started dating, in my first semester of graduate school. she was the associate editor-in-chief of the school literary magazine and i was incredibly dismissive of literary magazines because i had way more Tumblr followers than our school's magazine had subscribers so why the fuck would i go through waiting months in a slush pile in order to maybe publish something i could just definitely publish myself right now. luckily, she didn't find me so totally obnoxious she didn't want to continue dating me (i also went on to be the nonfiction editor of the magazine and published things i was proud of, even though i'd never submit my own work anywhere like that). my feelings about a paywall for my own writing have always been that i want to be read and paywalls are an impediment to readers and i'm never going to earn enough from the kind of writing i like to do that i don't have to have a full-time job for salary and benefits, and if i have to have a full-time job anyway, i'd rather do whatever i can to be read as widely as possible.

but like also i don't actually really believe that, because if i did, i'd, at the very least, have a Substack! they pitched me multiple times over the years and sometimes i think: could i have gotten a hundred thousand dollars? could i have gotten a book deal? my artistic career has been a history of saying no to things that in retrospect i probably should have said yes to. in the past, saying no was often because (unmedicated) anxiety made the things that were being proposed feel impossible to me as much as it was any kind of principle or commitment to the idiosyncracy of my art. when people ask me about starting a newsletter now, i tell them in one breath that, personally, i hate Substack

and then, in the next breath, i tell them that if they want to start a newsletter from scratch and don't have an existing audience, Substack is basically the only rational choice. the network effects they can provide are too powerful, especially for shy people (like me) who want promotion to be a more ambient thing they can do by liking and commenting and not something that requires actively selling yourself. i hate Substack (in addition to the previous clip, celebrating Richard Hanania, and you know, making money off Nazis, their biggest success story is metastasizing the national cancer that is Bari Weiss!) but i still pay them money every month anyway because there are writers i love there trying to make things and i want to support them and experience their work. i don't believe in purity tests; most platforms worth being on are compromised in some way or another **. that sucks, but we do what we can on the margins to try to lift up good things from the muck.

so, one more plug: if you want to support my favorite writer and artist, check out Deborah's newsletter and her comics archive!!! i will close with one of my favorite of her comics, which is about our dog Miso misunderstanding cottage cheese as a place she can go:

* okay no unsolicited advice except last week we were sitting al fresco at No Saint eating some incredible sandwiches next to two women and one of them was talking about not having a good spot for Detroit-style pizza here and i did something i have maybe never done in my entire life which was to interrupt her and say "sorry, i overheard you and i just have to say the best Detroit style pizza in Portland is Wild Child" and the fact that i did this totally out of character thing is a testament to how much i fucking love that pizza.

** that said, if you have an audience already and you want to get off Substack, Buttondown, the service i'm using to send you this, is cheap, easy to use (but with a very powerful public API as opposed to Substack's nonexistent one), and run by good people. i like how Sasha Frere-Jones put it: