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Substack and the Writing Long-Game
Thoughts on slow and diligent writing while balancing the demands of the platform
Quick note: I was honored to be interviewed by journalist for her wonderful newsletter , which explores life after burnout and how to strike a balance between realism and hope. If you like the themes here at Inner Workings, you will definitely find a lot to love in Rosie’s work. It was a joy to reflect on my own story with Rosie, covering a range of topics from ambition to high sensitivity to chronic pain. I felt like I was speaking with a kindred spirit!
I wrote in my latest roundup about our modern relationship with time, and in doing so I started thinking about writing and time, and then, inevitably, the writing on internet. I have always viewed writing as a fundamentally slow act, one where any given day’s work is not likely to be material, but in fifty days I might see some progress. In particular, I hold a very long view when it comes to the project of improving at writing.
My mental model is this: if I write and write and write, then every year I might get just a bit more skilled, almost imperceptibly, like stacking one additional sheet of paper on a small stack. And then years later, I will look at the stack and it will be tall, and that is, I believe, the only possible way to become the writer I want to be.
There are certainly times when this idea feels impossible, or at least tiresome and annoying, times when I wish the process could just happen faster. But also, when I am able to escape for a moment from the Tim Ferris-esq cultural preference for doing everything faster and more efficiently, the notion that I might give whole decades over to slowly improving at something I find worthwhile can feel hugely liberating, like taking a big breath of forest air after a day in an air conditioned office. It releases me from a day-to-day feeling of having to jam everything in; as long as I do this one worthwhile thing diligently, then I can feel confident that I am putting one foot in front of another on this long and winding hike that I have deemed worthwhile. Ah, doesn’t that sound nice.
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My first nine months of writing on the internet have been undeniably rewarding and positive. For the first time in my fifteen years of serious writing, I have people reading and even responding to the ideas that fuel my inner life. This is perhaps the most rewarding possible outcome for a writer. I am regularly encountering other writers with similar interests and whose style I admire. I am building a genuine foundation for a career as a writer, a much more solid one than all my previous attempts, including spending five years writing an unpublished book, and publishing essays in print-only literary magazines.
And also. I have slid smoothly, seamlessly, almost without thinking, into the speed of this platform. I started out with the idea of publishing monthly essays, with a pause in August and December. Ten essays a year, a cadence which at the time sounded difficult to achieve but possible. These essays would be in the vein of this one on infertility and this one on being a woman in Silicon Valley: meaty, long, crafted, workshopped, written and re-written, hammered into shape over many months. For my paid offering, I would send around favorite quotes each week. Simple. Elegant. Plenty of time for slow writing.
Then, a few months in, that offering started to seem a little thin. Regular posting is important on Substack in order to be discovered and featured. So I started writing short essays every week, and one long essay monthly. Then I added a monthly roundup for paid subscribers, because that format seemed valuable and valued on Substack. So suddenly I was doing six posts a month, following all the Substack best practices. Then Notes arrived, and my new weekly cadence quickly took on more of a daily urgency, one that I haven’t been very good at, to be honest. But even if I’m not posting daily, then I’m definitely feeling bad daily about not posting daily.
The games we choose to play
I can’t help but think at this juncture about all the sacrifices I made when I was starting my company, all the little concessions to fit into the system and succeed within it. It turns out that I’m good at adopting the rules of the game set out for me by society, even when they make me miserable. So the cynic in me is saying, “here we go again, Rae.” I am a little disturbed by how naturally and easily I slid into my conformity with this platform’s demands. But then again, I want to be a writer. This is how you do that on Substack.
This is not a new story, the tension between creative work and commercialization, between the demands of your job and the demands of your soul. But it has been instructive to watch it happen once again to me and so quickly. I have been able, this time, to observe it with eyes wide open. As this all was unfolding, I came across this essay byabout being a writer today, which basically makes the case that the most highly rewarded skill now is being able to write anything coherent quickly.
“The cornerstone of internet success is not intelligence or novelty or outrageousness or even speed, but regularity. There are all kinds of things you can do to develop and retain an audience -- break news, loudly talk about your own independence, make your Twitter avatar a photo of a cute girl -- but the single most important thing you can do is post regularly and never stop."
I hated this conclusion, and it also struck me as deeply true.
So, what’s a writer to do?
I could easily and cynically conclude here that we are all doomed to be trapped in whatever platforms capitalism has delivered to us in our particular time and place. But that’s actually not how I feel, and particularly not about Substack. Actually, Substack has opened up a couple really interesting new modes for me as a writer: it has strengthened my ability to compose ideas quickly, and helped me build a habit of listening to reader feedback and responding to it.
If I think about the Venn diagram of “what Substack demands,” and “what I want to do as a writer,” the overlap is pretty significant. I feel really lucky for that.
The other major option for me, the one I’ve tried in the past when I failed to publish a full-on book, is to spend months or years putting my best work on paper, then to lay it at the feet of forty or sixty people in New York City and cross my fingers that one of them likes it. This path has certain advantages, particularly related to pace of work, and a lot of obvious disadvantages.
So to use the favorite phrase of, both are true. All platforms demand certain types of conformity to succeed, including this one. And also, for me, right now, Substack is an awesome place to write. My goal now is to approach the platforms I use with eyes wide open, aware of what types of changes they demand from me, constantly evaluating if these are changes I want to make, and particularly when it comes to my art. I don’t want to be a purist, devoted to my own way or no way at all, but I also don’t want to bend too far, suddenly finding myself to be not an essayist but a rapid snippet creator.
I have heard many times the adage, “the medium is the message,” and this theoretical idea becomes very concrete when I think about the changes I have made to my own writing in order to work well on this particular medium.
We need to be vigilant about how our message is being shaped by our medium, and watch for signs that that shaping is changing our voice beyond our recognition.
For me, right now, Substack’s demands are more helpful than hurtful. They give me a template and push me to try new formats, lengths and styles for my writing. They still allow for some, (though less than I would like), time for the long and tedious process of crafting what I would call Essays with a capital “E,” the work that cannot be done quickly, and which usually strikes much deeper in the hearts of my readers, obviously because it comes from a much deeper place in my own heart.
But, back to the game
Ok, but, let’s be clear, I am still playing the game. It is my nature. This newsletter is devoted to unflinching honesty, so I feel I must tell you. I am now seven paid subscribers away from getting a little “bestseller” checkmark next to my name, a completely arbitrary threshold that has been made extraordinarily significant in my mind because some team of people at this company called Substack decided to attach social proof to this particular number. God, this tactic worked so well on me—good job team. I want that checkmark. I want that checkmark so bad. I want that checkmark like drugs. Grrr I’m hungry for it. Even though I know that after a week the thrill will fade and I will be onto the next incentive provided for me.
But that awareness is my point. Making changes to our work and our rhythms based on the medium we choose doesn’t mean we have no agency with our voices. I think it means that we need to choose our platforms wisely, and use them with full awareness of their demands.
✍️ I’d love to know…
What Substack “demands” are you most consistently aware of?
In your own Venn diagram of “what Substack demands” and “who you want to be as a writer,” what is the amount of overlap?
What threshold are you hungry to reach right now?
Let’s talk about it in the comments!