Thank you, but I'm afraid I've since moved on. I already tried my own attempt at it here. ATM I'm thinking of writing a short ebook. But great idea and 100% would have been on board with it if I hadn't already tried to write a blog post a day.

Last week I finally and at long last managed to prompt an LLM into a "Socratic^[1] Brainstormer". It's really frustrating though that it doesn't ever hit me with a real curve ball that makes me go "Oh wow, I never thought of that" or "Oh shit, everything I said is a falsehood" a la Socrates. But as far as an rubber-duck with extra bells and whistles go, it's a step forward.

It has stopped with the overt sycophancy, no more "fascinating" or "what you've just said is very significant". It just asks questions, as few or as many questions as I specify. Claude seems to rely on a few stock question formats though, such as "which are the topics that cause people to lean in and take notice" "which common ideas/theories frustrate you or you find superficial?". It also tends to seek generalized patterns rather than specifics - my brainstorming about the theory behind colour schemes on movie sets leads to covertly sycophantic questions like "it sounds like this is a more all-encompassing phenomenological theory about how we create meaning from visual information" - no Claude, this is not. 

ChatGPT when it is prompted with words like"empirical" or "details oriented" tends to leap to questions about execution before I've managed to brainstorm the core ideas. If I need a theme for a content calendar, it'll already be asking me which metrics I'm going to use to test reels on Instagram against each other - Sorry GPT, I don't know what variable I'll be using the metric to measure the success of yet.

What's, perhaps, most noteworthy is how giddy and excited I was when I finally managed to get purely inquisitive responses. I actually was grinning at the prospect of having an indefatigable personal interrogator who would as slyly as Lt. Columbo ask me leading questions to help me discover curveballs and new ideas I couldn't possibly arrive at on my own. I keep searching...
 

1. ^{^}

   By "Socratic" I mean here, purely the sense that it asks a lot of questions. Sadly I haven't managed to successfully prompt it into making use of Socratic Irony - identifying paradoxes or forcing me to admit the polite fictions that expedite social intercourse even though I know they are not true.

it seems that one often believes being self aware of a certain limitation is enough to correct for it sufficiently to at least be calibrated about how limited one is...and then act as if because they've acknowledged a potential failure mode and will try to be careful towards avoiding it, that they are much less susceptible to the failure mode than other people in an otherwise similar reference class.

I don't follow. If I know I don't "handle" spicy food well, so I avoid eating it. Then I'm not acting as if I'm less susceptible to spicy food because I've acknowledged it. Or are you talking about the proverbial example of someone who drives after getting tipsy, but believes because they're more "careful" they're safe-enough?

As for brainworms - I'm not familiar with that term but can guess it's some kind of faddish toxic behaviour (I'm struggling to think of a concrete example, perhaps the use of bromides and platitudes in conversation like "keep your chin up" in lieu of tailored comfort and discourse?) - but what might be an example of a rat-brainworm and an analogous normie brain worm?

I'd like to see this translated into more prosaic English because I'm not exactly sure what it's arguing. Also I'm on guard against statements like "humans seek" or "man cannot behold" as I always suspect they are typical-mind fallacies leaking unless supported by specific arguments.

I feel not taken in by LLM chatbots obvious sycophancy. I'm not sure if this reflects well on me, or is a sign of low self-confidence and that skepticism of praise and compliments is my baseline.

If I understand you correctly the purpose isn't the journal itself (using stickers and pretty stationary aside), but it affords inducing a kind of Baader-Meinhof Phenomenon: where one is primed to notice moments of joy in their day? But unlike the Baader-Meinhof Phenomenon or Frequency Illusion which is unintentional - the idea is to actively and intentionally habituate it.

In the same way, and I'm wildly speculating here, that a jeweler begins to "notice" qualities in gemstones over time? A jeweler, say looking for faults in diamonds, over time will just twist it in a certain way, and intuitively "know" what to look for.

I'm clearly missing something here, do you mind over-explaining it to me?

The idea is that it trains you to pay attention to, and remember to savor, positive events in your life, which in turn will improve your overall enjoyment.

But that is limited by the things which genuinely produce an above-baseline level of joy, then how does that train me to do anything since I already need to be in the habit of noticing them otherwise they don't get journaled? And what if I know I should be grateful for getting paid today, but I don't feel joy about it - if my genuine feeling is "I should get more" - how does that factor in? Surely the person who feels they deserve more is the exact kind of person who needs to journal gratitude because they aren't having enough gratitude - but if you're not meant to journal things which you intellectually know should or are supposed to be grateful for, but don't earnestly feel it - then how does this work?

And what if on a given day, nothing brings me joy, It's a really "some days it doesn't pay to get out of bed" kind of day? Again, surely those are the days where a gratitude is paramount - to somehow reframe the day?

I know I'm missing something here, or maybe there's some implicit assumptions I'm bringing which are warping my understanding.

maybe the reason you didn't see any improvement beyond the edification of your self-image as a person who does awesome things no one does because you didn't do the awesome thing (i.e. keeping a gratitude journal) correctly?

The reason say this is I don't understand how a Gratitude Journal works. I feel like it is absurdly easy to quota fill a journal every day with things I am supposed to be grateful for, even if I'm (and I hope I'm not) an entitled and spoiled brat who feels like the world somehow feels the world owes me more than I've received.

"I'm grateful that I have eyes, I saw a caution sign and avoided tripping and injuring myself, some people are blind, have diminished vision. They may not have seen the sign. I'm grateful for the vision I have."

"I broke my favourite mug today, I'm grateful that I had a favourite mug at all and got to enjoy it for the two months I had it, and further grateful that I'm not so destitute that I can't afford to replace it"

It seems like it's very easy to come up with these things, especially if you're allowed to repeat them day after day. But how does that process help?

Being a person who does awesome things that no one else does is only effective when you do awesome things correctly. I don't know - maybe you were doing it correctly. 

I struggle to write cover letters for applications^[1], despite being self-aware. The obvious remedy would be to lie and make up what skills or abilities I have based on the application, and hope there's no negative repercussions later. I see my difficulty in writing cover letters as part of a wider pattern of being unable to answer the question "what am I good at - that people need enough to pay for?" which is a fundamentally different to the questions "what am I proud of?" and "what are my passions?". Writing a cover letter involves not only identifying the tasks which are easy or hard for you and skills you possess; but then ranking those against a theoretical sample of others - such as the pool of other applicants you're competing with. How accurate you can rank yourself improves your cover-letter writing and general application strategy.

You can be really good at calling out the title of a Tin Pan Alley song from someone just playing a few bars, but who's (realistically) going to need that so much they will pay you regularly for it?

Why did I mention passions: there is a common sentiment that you should follow your "passion" and find a career in that, rather than do something "for the money" and end up hating your job and your life. I personally think following your passion over money is bad advice, but I feel like if I don't mention "passions" someone will in the replies.

Some people are really passionate about Taylor Swift's music, like they might be able to talk breathlessly about her discography and the enumerate minute differences between (Taylor's version) and the first recordings. But there's probably a glut of supply for those skills making it virtually impossible to monetize.

If we change the question entirely to "what should I upskill in?", this certainly opens up new possibilities, so much so, that the breadth of possibilities leads to analysis paralysis. It might be easier/wiser to instead ask "what must I not upskill in?" and shrink the possibilities based on some principled "whys?" and reasoning.
 

1. ^{^}

   Jobs, grants, proposals, even lead generation as a freelancer - anything where you need to "sell yourself"

You forgot the seemingly platitudinous but actually important one: how it makes you feel. 

I'm not kidding. Something that makes you feel exposed or overcompensating can and will affect your posture, your body language, which will attenuate the "impress" factor of your choice of outfit on the audience. This extends beyond wrong sizing, or fabric: I'm talking about the effect of self-consciousness about an outfit (which is a high probability if you're going outside of your comfort zone, and wearing something "to impress") affects your physicality.

But also, what do you mean by "impress"? I assume you mean a certain degree of ostentation? Does "dress to impress" always imply a relative "overdressing" for the occasion, i.e. more formal but ostentatious relative to the baseline of how everyone else in the setting will be dressing?