michael-dean-k/

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).

It's a mistake to think of effort as a single spectrum between a Gary Vaynerchuk grind-till-you-die flip-slop-on-Facebook-marketplace vibe and a Wu-Wei, non-effort, sabbatical-brained, Netflix-and-chill vibe. Something not on that spectrum is obsession. It's not work for work's sake, or work for status climbing, but work by seduction, by tinkering, by vision, by purpose or duty or whatever. It often can look like grind work in terms of focus and intensity and prolificness and hours spent, but it feels different because it comes from a different place.

I framed this question to my cousins: would you rather work hard for 8+ hours a day on something you feel compelled and intrinsically motivated towards, or, go into an office for 8 hours a day for a bullshit job that only requires 1-2 hours of simple work, mindless and purposeless work, and then spend the rest of the time socializing?

The word "work" itself is a bit tainted, because there's a sense of obligation ("I have to do this to get paid"), sacrifice ("I'm doing this at the expense of things I love to support us"), and utility ("I'm making things that are functional for other people"). The work that I'm most drawn to is something like the inverse of this. It's pleasurable ("I lose track of time doing this"), primary ("There's nothing else I'd rather do"), and visionary ("I'm doing this because I see the value in it, and even if others can't see it now, they may eventually.")

A big shift in my way of working: instead of trying to scope a specific and ambitious batch of tasks I think should be done in a given day or week, all I commit to is time towards specific areas. The deadlines are less important (generally) than making sure I show up and do high-leverage work with 100% embodiment and enthusiasm. I just set up the Streaks app, and aim for 2.5 hours of work per day over 6 areas: writing, coding, reading, outreach, business, and culture. Each is a simple target: 20-45 minutes per day. At the very least, it gets me started. If I’m in a flow, I go over as long as I want (1-2 hours or more). If not, I just stop. The goal here is to rethink what work might look like while caring for my daughter (and my post-labor wife). I could potentially knock out 2.5 hours in a single nap cycle, or maybe it’s spread over 3-4 sessions at random times. It forces me to prioritize an important thing per day in an area that is an infinite game. It feels slightly unambitious, but I actually think an OS of this nature might be something I continue even when I “get my time back.” There’s a forced prioritization, as well as open space to either (a) diverge/explore, or (b) drill deep on things that actually matter.

Intuition is romanticized, as if all thinking is too controlling, and all the answers we need are simply waiting inside us. I think this is wrong. I mean, of course, intuition could be the secret sauce, if it’s well-trained. Your intuition lets you think and do without thinking; this covers gut decisions, but also fears, procrastinations, biases, etc. 

So how do you train it? (1) Practice, repetition, mantras; (2) Metacognition: the ability to know when reason or intuition serves/betrays you; (3) Journal analysis: dumping thoughts is the beginning of the process, but I don’t believe getting it out is enough. The point is to look at your feelings and make sense of them.

What these 3 have in common is that they all require thought. By analyzing and running experiments on yourself, you train your intuition so that you don’t have to think in the moment.

If you want better intuition (a state of non-thinking), you will have to first do a lot of hard, deliberate thinking.

Act as if every minute you scroll drains half your day’s potential. It’s not just a break, but a minute you’re not meditating, reflecting, journaling, creating, practicing, etc. A bad break is a minute you’re not reviving your systems. Instead you atrophy your attention and trend in the negative direction. It affects the nature of your focus for the rest of the day. After just 5 minutes scrolling, you’ve shot 97% of your days potential. This isn’t literal, but act as if it’s the case. More so: realize the returns of taking good breaks (of actual leisure).

In my first 100 days post-WOP, I wrote every day and basically published nothing.

What helped me snap out of that rut was to take on a mindset of "single session publishing." This means I sit down for a writing session and don't stop until it goes on my site (sessions were 2-4 hours). They were effectively first drafts, and sometimes I'd come back to revise them. I didn't "blast" them to my email list, but DM'd them to specific people to start a conversation. There was something about having a body of work on my website that took the pressure off (eventually) sending essays to my larger list.

I'm 100% a perfectionist, and think it's worth having a rigorous, increasing quality standard, but it's important to also have places with much lower standards to serve as your release valve.

Also, publishing under my legal/professional identity came with all sorts of psychological blocks that were completely invisible to me until I started publishing under a pseudonym. Every situation is different, but I wonder if shifting to semi-pseudonymous Substack would help take the pressure off everyeone.

I’m sort of inspired now to create a section on my own Substack called “Drafts.” You can customize that so new subscribers by default aren’t on that list. I currently have an “Experiments” section on my site, but “Drafts” feels a lot more self-explanatory. (Some of these drafts will eventually reach “peak” form and get reposted in the Essay section, but that won’t happen with most of them).

Some points to consider for the age of AI:

• Have a bold vision for your life and art.
• Don’t compete with commodities or status.
• Make yourself legible to machines.
• Turn your frameworks into code.
• Start a vlog.
• Go off-script.
• Take leisure seriously.
• Meditate multiple times per day.
• Join the Boy Scouts.
• Stop watching porn.
• Aim to be sublimely well-rounded.
• Embrace for the weirdest possible future.
• Be humble as you lose your edge.
• Accept death in this hour.