facing reality, pt 1

people can be remarkably skilled at NOT learning from experience

REMEMBER, a meditation by wanderweird

here’s a little challenge for myself: i wonder if i could write something in 30 minutes while sleepy and be satisfied with it enough to hit publish on it. the first thing that seems to go out the window is capitalization, though the moment I say that I find myself reaching for the capital I, semi-reflexively. I wonder if I intend the i to be read differently each time. is it a purposeful choice? i’m sort of feeling it out. writing is music. i don’t know in advance where i’m going, and i might switch back and forth a little bit to see how i feel. there isn’t actually a correct answer re: how to do this, the correctness is something that emerges. and that emergence is interesting to me, which is a big part of what compels me to keep writing.

which reminds me– recently i got a DM from a random stranger asking why I don’t use “proper punctuation” when I tweet. I experimented with typing out several different answers and i wasn’t quite satisfied with any of them. what i wanted to say was that i reject the premise– I don’t believe in the notion of “proper punctuation” in some fixed universal sense, but I wanted to say that without saying directly that I reject the premise– that would’ve been more brusque than i’d have liked, in that context. let me check for what i ended up saying… I wrote back “my tweets are punctuated as my tastes and style dictate”. Which i think is quite a clever bit of “focus on what you want to see more of’– i didn’t directly agree or disagree, but rather put forward my own interpretation of how and why i tweet the way i do. He responded with “😔 it diminishes the readability”, to which I replied with “i don’t care”.

“Would you care if I wasn't just 0.0012% of your followers?
”i didn't care even when i had 0 followers”

the conversation predictably kinda dried up from there¹, but i do actually have more to say on the topic. which is that i believe that it can be very worthwhile to sacrifice readability to prioritize ‘writability’. which is another way of stating the title of one of my previous essays on here, resonance over coherence.

WRITABILITY OVER READABILITY

obviously one can go too far with this. I don’t want to be incapable of coherence. and I don’t want to write stuff that is absolutely unreadable. but once i can trust myself to produce output that is moderately coherent and moderately readable, i want to optimize for resonance, and in parallel, for quantity of output. it’s complex. it’s ecological. i don’t have a singular metric and a singular monomaniacal focus. i believe that that’s part of why i’m interesting to read, because it’s not always obvious from the start where i’m going and what i’m trying to achieve– not even to myself. now: the capitalization and punctuation in this essay might not be super reader-friendly. i know. the reader-as-consumer might see such a post and think “ugh, this post was decent, made some good points, helped me look at something from a fresh point of view, but god was it annoying to read”, and they could be right on all counts, and yet not quite appreciate that if the writer had to make it less annoying to read they might not have written it at all.

few people really appreciate this, apart from seasoned creators and practitioners with lots of experience. to use some sports/fitness analogies, i’ve heard from a lot of serious longterm players that you want to do whatever it takes to avoid injury, and then beyond that you mostly want to have a good time. this is so that you feel compelled to do it again. it’s the training volume that gives you something to tinker with. there’s little value in going hard for 3 months if you then get burnt out and can’t compel yourself to keep going. it’s over years that the real gains start to accrue. and fitness is one of the riskier domains! if you attempt something too strenous when you’re exhausted, you might get a bad injury that throws you out of the game, and still continues hurting you even when you’re out of it. thankfully there’s almost nothing like that in the creative spheres. except maybe if you say something so egregious that you get ‘cancelled’. but that’s fairly easy to avoid if you have any sense. maybe people struggle because they’re not sure if they have any sense. it’s rarely the uncertain who get cancelled, though. it’s those who are erroneously sure of themselves. all my homies are full of self-doubt. we question ourselves a lot, that’s a big part of what makes our work any good.

but yeah, what i wanted to say here, mainly as an affirmation to myself, is that i want to prioritize writability over readability.² I want to WRITE, goddamnit! and here a part of me wants to say “yea ideally all of my stuff would be beautifully readable, well-formatted, perfectly paced, beatific, no wasteful sentences…” but immediately i find myself in conflict, because (1) i know that that takes a lot of time and effort, which may be better allocated elsewhere, and (2) i’m not even sure if i believe that to be always desirable.

there are circumstances in which sketchy unpolished work is actually superior to perfectly polished work, maybe roughly akin to how there are some contexts where you can be overdressed to the point of being stiff and awkward, or otherwise forced, fake and so on. when i wrote my 2nd book Introspect, I was very much torn up about how the recommendations I was making had a polished confidence to them, and I wanted to find a way to emphasize that the actual process of introspection in my experience tends to be halting, tentative, kinda awkward even. but i didn’t want to write a halting, tentative book. that would be a pain to read. i can’t remember how precisely i arrived at the compromise that i now love: i split the book up into 5 acts, and in between the acts i would have these “unedited ramblings” sections, where i would write roughly like i’m writing now. actually even more chaotic than i’m writing now. and many people have DM’d me to tell me that those are their favorite sections of the book– because you just don’t encounter anything like that in the polished tomes you find at airport bookstores and on bestseller lists. it’s honest. it’s earnest. someone said “it’s almost too real”. to which I say fuck yeah, if it’s not real then why are we even here, ya know what i mean? to quote the famous poet-philosopher Jon Bon Jovi, i just wanna live while i’m alive, man.

✱

the above sentence would be a pretty strong place to end a post, but i’m not satisfied yet. i feel like i have at least one more “hit” in me. i’m starting to find my footing with these posts. i’m starting to get a sense of how it feels from the inside, how it feels from start to finish, how i want it to feel, what i want to accomplish. i think i struggled for a long time with these essays because i kept thinking about them instead of fucken writing them out. tragically hilarious. i have been an overthinker all my life... yup, that’s where we’re going and we’ll ride this one out to its natural conclusion, lets go!

OVERTHINKING (IS NOT THE PROBLEM)

(source tweets)

i’ve thought a lot about thinking over the years, some of it useful, some of it not. (sidenote: there’s a common go-to flavor of joke about procrastination, where someone might maybe make a video about how to deal with procrastination, and the top comment will be “looks like a great video, i’ll watch it tomorrow”. cue laugh track, 10,000 upvotes, well done everybody. ha ha. i don’t know how many times i can politely laugh at that one. I think for me it wore thin after about 10 years.) back to thinking and overthinking. there’s a similar pattern here, where… if you begin to talk about overthinking, some people will reach for the go-to flavor of joke about overthinking the overthinking. this can range from the low-effort recursion joke, to something sprawling and magnificent, ie responding to overthinking by overthinking, writing a whole essay in the comments. sometimes this can be really artful, sometimes intentionally, sometimes not.

but i’ve similarly grown tired of the overthinking jokes just as i’ve grown tired of the procrastination jokes, particularly when i sense that they’re intended, consciously or otherwise, as acts of avoidance. (to spell out the recursion: people are not only relying on copes to avoid facing painful realities, they are avoiding facing the truth of how they are relying on copes to avoiding facing painful realities. I used to find this funny, I now mostly find it sad.) i do understand that sometimes these can be important safety rituals for people. procrastination and overthinking (and overthinking is a form of procrastination) are both safety rituals in that they keep you safe from the emotional discomfort of actually doing things that may have consequences that you may not like. (this was a substantial topic of discussion in my recent essay a stupid bravery).

i don’t think safety rituals are necessarily bad. they’re meant to keep us safe. and you know what, i’d argue that even ordinary thinking is a safety ritual. and a good one. it’s often worth taking a moment to think through your actions, simulate the possible outcomes, and then have your thoughts guide your actions along good paths, steering away from costly pitfalls, dead-ends and so on. But rarely is it possible to think through all possibilities, except in particularly constrained domains. Life can be very open-ended, and a well-thought-out model of possibilities can still be limiting if you cling too tightly to it, since it will have you overlooking possibilities that you couldn’t even conceive of when you started thinking. Remaining open to possibility is a particularly invigorating practice. I’ve found it critically necessary to re-learn how to do this in the context of these essays. To write anything good I have to be open to the possibility that something is going to come up mid-essay that’s going to be more interesting than what I had in mind when I set out.

[[ i’m now reminded that many years ago when i was seriously passionate about digging into the truths of my own procrastination and laziness,Ii came around to using the terms like “task aversion” or “task avoidance”, which I do think are more useful frames. the word “procrastination” isn’t very evocative or concrete. it isn’t immediately obvious from the word itself what you ought to do about it, apart from “maybe not do that?” – whereas if we talk in terms of aversions and avoidance, I find that it feels a lot more natural to ask, “why are we avoiding this?” And from there we can work towards finding a solution.

“Task-aversion” implies that there’s a mismatch between the task and the person, whereas “laziness” or “procrastination” tends to locate the problem entirely within the individual. Which wouldn’t be all that bad if it worked, but I’ve had a lot of experience witnessing it not work, and I’ve talked with hundreds of people at this point who’ve had the same problem. If you define the problem as laziness, it’s hard to find solutions. If you define the problem as task-aversion, it’s a whole lot easier to navigate. Sometimes the task should be avoided! And it’s usually quite clear that very few people are averse to all tasks (and those people are usually severely depressed, have health issues, etc). A lot of young fellas who are “lazy” when it comes to their schoolwork can be remarkably industrious when it comes to something they enjoy, such as video games, or movies, or music, or some other more particular thing. This simple fact (the specifics of which may vary from person to person) refutes the simplistic notion that “the person is lazy” in an absolute sense. They are lazy in some contexts and industrious in others. From there we can begin to piece together how and why that is. ]]

so where are we on overthinking? someone DM’d me once asking me “how do I stop overthinking”, and my response was to ask “why do you want to do that?” – and there’s a reason for that. the point is that overthinking by itself is not a problem. the problem is that it’s keeping you from doing something else. and the way to do that something else is not to try and overthink less, the way to do the thing is to focus your attention on doing the thing. in my case, i spent at least a year overthinking my essays. that’s not a bad thing. the bad thing was that the essays weren’t getting written, weren’t getting published, and the longer i went without publishing essays, my writing-publishing muscle atrophied, and any thing i might write or publish gets overburdened with more perceived significance, which made me overthink them even more.

the only way out past some point was to basically give up, accept defeat, realize that i wasn’t going to accomplish the thing that i was hoping to accomplish, and that i should instead ask myself, “what would it take for me to publish an essay, really?” and the thinking i did to answer that question was actually fruitful, as opposed to thinking more abstract, fanciful questions like “what is the ideal configuration for a set of essays to create a truly sublime gestalt”. And now that I write that down I find myself thinking, that’s not necessarily a bad question to ask, either. I’m glad that I spent some time pondering that question even if I ended up with “idk, lol”. Truly! I believe that the act of pondering is itself valuable somehow, in ways that are hard to articulate. They inform my “posture”, or my “approach”. I’m always thinking about it to some degree. It’s just that I have to carry with me, simultaneously, a question of “how long has it been since I published something?”

Thinking has to be balanced by doing. Reflection has to be balanced by action. That’s how you calibrate it. (One could also hypothetically have the opposite problem, where you’re overdoing things and ought to pause to think and reflect. You don’t have that problem though. Underthinkers don’t read essays.)

✱

the rule of thirds is a powerful one. a 3 part essay somehow almost always feels more “right” than a 2-part essay. unless the 2-parter has a particular wes anderson-y symmetry to it, which the above two parts don’t. so now I find myself drawn to an interesting question of, given the first matryoshka being about writability and the second being about overthinking, what should the third one be? I don’t know yet. i had to take a break while writing this when my 6 month old son woke up crying, and while soothing him back to sleep i was thinking about how i might finish this essay. i pondered that maybe i could go with how the ‘writability over readability’ choice is an example of defeating overthinking, and how that comes with tradeoffs. aha, i know what the final third is going to be, we are going to talk about…

FACING REALITY

I’ve written some tweets about this recently in response to another person’s DMs:

(source tweet)

If I were to rewrite the thread I might choose to say “refuses to learn from his experience”, which is a little more broad than “from his mistakes”. And honestly I think the reason I wrote this thread is because I always see myself in this type of guy. I am myself still this type of guy, particularly in this domain of writing essays! And the lesson I keep having to learn over and over again is to FACE REALITY. Which can be painful, uncomfortable, etc.

I’ve written many posts, essays, tweets etc about this over the years. I keep having to come back to it again, rediscover it again, and I’m starting to make my peace with the idea that maybe it will always be that way, the same way we need to eat and sleep repeatedly. You don’t just do it once and be done forever. It’s part of a continual process. And as I write this now it occurs to me that it’s part of the tension of “being a visionary”, which always sounds a little grandiose, but I mean in a rather practical everyday sense of having some particular vision for how things should be. Immediately you’re in tension between reality as-is and the vision of what-could-be.

Most recently I had a conversation with my longtime mentor and friend Dinesh that ended up in this territory– he cleverly got me to see again that I have been playing it safe for some time now, optimizing for a psychological sense of well-being rather than tangible outcomes. Trying to make tangible outcomes happen is scary. You could fail. You could look stupid. You make mistakes that people can point and laugh at. If you succeed you may alienate some of the people you thought of as friends. There’s unpleasantness lurking at almost every turn, and again, it takes a ‘stupid bravery’ to take the leap of faith into the unknown. I don’t know for sure why exactly John Mayer used the adjective ‘stupid’, but if I had written that phrase I’d know why I chose it– it’s because it feels stupid to not do the “smart” thing, which is to say to overthink everything, overanalyze everything, keep everything in production hell forever, where it’s safe. And then when it’s eventually clear that the thing is overwrought and it’s moment has passed, start all over again with new projects that are to be analyzed forever without shipping anything. Repeat.

When you frame it like that, it’s obvious that the “smart” thing isn’t smart at all. It’s safetyism gone rogue. Well I’m tired of playing it safe. I want to reorient to focus my time and energy on tangible outcomes that I want to achieve. I want to dare to risk failure. Part of that means shipping essays that feel unfinished and incomplete. I started out hoping to spend 30 minutes on this essay, which ballooned into 4 hours. That sort of thing has happened a lot. But what doesn’t happen so much is me actually hitting publish at the end of a work session. Maybe if I do 100 of these, I might change my mind about how I ought to do these. But for the foreseeable future, at least for the next 20 or so essays, I think I can afford to post some “unreadable” rants.

I actually have a lot more to say on the topic of Facing Reality, but alas, my immediate reality is that it’s 427am, I have run out of steam and need to go to bed. But I’d like to write more about it. Maybe tomorrow? We’ll see.

1. I do know how to keep a conversation like that going, but it involves effort on my part to ‘soften the ground’. I’d basically be carrying the conversation for both of us, and while I like knowing that I’m capable of that, I didn’t feel compelled to do it in this particular context. And over lots of time and interactions, I’ve found that I can’t actually sustainably carry every conversation– I start to get bitter and resentful if I’m always doing all the work. So I do it when I personally feel compelled to do it, and I don’t when I don’t. Writing an essay about the conversation that I could have had might come across as petty, which is something that in the past I’ve agonized about too– but here too I’ve ultimately arrived at a position of “I do not care”. I simply be true to myself and trust that the people who appreciate it will appreciate it, and the people who don’t are welcome to move on to whatever they prefer.

2. on prioritizing writability over readability: i kinda already knew this to be true, which is why i wrote resonance over coherence, and yet this is somewhat novel territory for me, in that i don’t really feel like i’ve published an essay like this one on this substack. this essay is an act of self-persuasion, and an act of affirmation.