michael-dean-k/

On Monday 6/15, I'm hosting a workshop to kick off a reading group for classic essays: RSVP here.

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Advice to a writer

· 655 words

Hey [ * ],

Don’t apologize for rambling; a good part of essay writing is just following a train of thought to see where it leads (and editing after). I enjoy your letters. You can articulate things well, and shouldn’t feel insecure about your words, or feel like you need to use AI.

I think your problem might be the need for certainty before you start. It sounds like you want to know your topic in advance (*), frameworks on how to make an essay, and the standards on what makes it great. These are all important, but I think you’re clinging to them pre-maturely; I don’t think you need to worry about topic, process, or quality until you’ve published 50-100 things. To start, it’s more about establishing the routine of becoming a writer, and once that is flowing, and once it’s almost guaranteed that you will publish something at your ideal interval, then you can start tinkering with other variables, testing if you can incorporate some new goal without interrupting the momentum.

I went through a very similar thing. I took a writing course, Write of Passage, published 2-3 essays, but then stalled. After it was over, I showed up for 100 days straight to my small writing group, and even though I thought, wrote, and edited every day for 1-2 hours, I didn’t publish anything. The core realization is that the process was getting in the way, and I was held back by my own standards prematurely. It’s all about publishing. Thinking and editing don’t count unless you bring a thought to a point where you’re willing to share it. Starting January 2021, I published 1 idea every single day for 45 days, and from there I’ve been publishing semi-regularly for 5.5 years (and through that time, the process continually evolves, and the quality bar varies but generally averages upwards). I’m almost at a million words now. All my thoughts from 2020 and before are mysterious and fuzzy, because I never froze them, and so I can’t know exactly what I thought back then. My most important thoughts since are all legible, and even if they’re poorly written and wrong, I’m happy I have them, for they’re a record of my own evolution.

My advice to you is to start a simple website where you can publish your thoughts every day. Daily publishing is a strong way to break out of a rut. It’s surprisingly doable, and forces you to get out of your head. You should have no expectation for it to be good, no sense of process (imagine writing a stream of consciousness letter like you did to me, but every day, on different topics), and no commitment to a topic (no more than 25-50% on X or Y). These don’t have to be good. Most of them won’t be. But by having them in public, you’ll care about them more, you’ll re-read them, maybe retroactively edit them; but of your first 30, you might have 3 that you’re really proud of, which is 3x more than if you tried to make 1 perfect piece per month.

I don’t think Substack is a conducive place to start this project, personally. If you publish 30 times and get 0-2 likes on each, it will feel like a failed project; if you do that same thing on your own website, it will feel like a massive success. If you don’t have an idea of where you would host your writing, let me know and I can offer suggestions. I’ve created my own site recently with Obsidian/Claude/Github/Netlify, but to start it’s not worth getting hung up on infrastructure. Spend no more than 15 minutes on your setup. There are plenty of minimal blogging platforms that will let you get started.

Let me know if you’re up to experiment with hyper-publishing. It’s about publishing every day, regardless of length (could be 40 words or 400 words).