When I was a teenager, the dominant criticism my closest friends had of me was that I was too arrogant, and they were right. I was too caustic, abrasive, eager to nitpick, quick to criticize, and I was way too certain of myself. I spent my entire 20s trying to correct for this.

The social niceties stuff were relatively trivial for me to address. learning to be gracious, patient, I could manage all of that. But “too certain of oneself” goes order of magnitudes deeper. It goes into philosophical territory about risk, certainty, the nature of knowledge

I very seriously experimented with beliefs like “almost everything I know is wrong to a degree I do not understand”, “my mental models are contaminated beyond repair”, “I have been indoctrinated and need to be deradicalized”, I subjected myself and my mind to radical rewrites

Over 8+ years I wrote over 800,000 words of introspective journaling, investigating my own mind, investigating the investigator. I read & talked to thousands of people from around the world to seek out different ways of thinking, seeing, being, believing, knowing, understanding

I tried to think of myself as a robot that needed debugging. I actually made substantial progress with that. I tried to think of myself as a garden that needed tending. I made substantial progress with that. I tried not to think of myself at all, and in some blissful moments I believe I transcended progress itself.

I experimented with trying really hard, and I experimented with not trying at all. I experimented with scheduling and calendaring my life, and I experimented with throwing everything to the wind. I questioned everything several times over, and I questioned nothing.

And… at the end of it all… in the middle of it all… I attained a level of calm clarity that, ironically, gave me even more of an aura of “certain of himself” than ever before. I know how it looks, I know how it sounds, but my priority is to live and speak honestly.

It’s not that I don’t make mistakes. It’s not that I don’t get things wrong. I do. But I am like a musician who’s skilled at improvising – I recover from my mistakes gracefully, I work them into my playing. What troubles some people is that I am insufficiently self-deprecating.

And I am not a “natural” at this – this skill is something I’ve picked up from a 15+ years of practice and study, the way a skilled musician would. And I talk about it openly because when I was a kid I wished someone would tell me this stuff, and nobody did, not quite.

I can return now to my friends’ original criticism and discern what they were trying to say, that they couldn’t quite articulate properly. there are many different latent messages encoded in a statement like “you are too certain of yourself”.

1. your frames are too rigid → this is something you can fix by learning to be more flexible with your frames.

2. you are too confident → this conflates bluster and bravado (bad) with the casual, sleepy ease of having deep knowledge.

I have rebuilt myself from scratch in the absolute wilderness, in total isolation, in the dark night of the soul twice having done it before, I know I can do it again. The result is a kind of fearlessness that attracts some people and repels others.

Recent meditation has made me realize that I have been trying to mask this, trying to suppress this, to be polite. To be civil. To not be arrogant. To not intimidate and scare people. But this is dishonest of me, and I want to live an honest life.

btw, here are some of the things that my friends were telling me I was cocky and arrogant about:

1. that I was going to marry my first girlfriend (I did)

2. that I was going to build an international audience (I did)

3. that I was going to make a decent living without going to university (I do)

4. that university professors would want to hang out with me, an autodidact (they do)

5. that I was going to be hired for somebody who respected my idiosyncrasies, without a resume (I was)

6. that I would have a successful business and be invited to speak/lecture at universities (done that)

7. that my band would play at the esplanade powerhouse stage, despite not being great musicians (we did)

8. that I would be the #1 search result for my first name (pretty much?)

9. that I would write and publish books that hundreds of people would want to buy and read (yep)

I could go on. Looking back, I think the right frame is: they witnessed me disregard their internalized shared limiting beliefs, and saw this as a status violation on my part.

Looking back, I’m not sad that they were wrong about me. I’m sad that I allowed them being wrong about me to let me be wrong about myself. I definitely allowed their thinking to contaminate mine. Hanging out with unambitious people definitely dimmed my own ambition. Never again.

Also, they never admitted to being unambitious – a thing that I might’ve been mad about a few years ago, but now kinda chuckle about. It’s absolutely fine to be unambitious. You can live a good, simple, worthwhile life. The worst thing here is the *pretense* of ambition.

People who *pretend* to be ambitious waste the valuable time and energy of actually-ambitious people, sucking them into their sitcoms and distracting them from the actual adventures they ought to be going on.

But, yknow. people gonna people. there’s no sense in getting mad about it. the thing is to focus on finding the people who get you.

I am not looking for people to affirm me, tell me I am so great, agree with everything I say, etc. I don’t want that. I don’t want fanboys or haters (who are fans too). I’m looking for other creative, ambitious, playful people to play with, folks who prioritize doing cool things.

I am here to find the others. Part of doing this means volunteering to be hyper-visible, which means being vulnerable to attack. I debated with myself internally, extensively, for years. I didn’t feel worthy, and simultaneously, I was afraid.

But when I see the friendships that people forge with each other in my mentions, I realize it is the right thing to do. I would honestly kinda prefer it if there were someone else I trusted to take the lead… but nobody sees things quite the way I do.

If the laws of physics don’t forbid it, then it’s mostly just a matter of figuring out the steps along the way.

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Humility (jul2021)

I want to collect some of my past utterances about humility.

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it’s a lil annoying that there’s a script for false humility because I really mean it when I say that, when I look back on my life and count the sheer number of people who have helped me, it’s impossible for me to see myself as some atomized individual. I am a team effort. I can’t take full credit for myself. I would not be me if I wasn’t also a we. Some people say this as a bit but I think it’s deeply true all the way through. I literally would not be here if not for the people who supported me, believed in me, saw the best in me, encouraged me. I live my life in dedication to them, and to pay their gift forward to the other kids.

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False humility has been a theme for me lately. I believe that the fastest way to puncture it is to step outside your existing context & engage with a different context. There can be no pretenses when you are in a context you don’t understand, where there is mystery, excitement, danger.

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Faux humility rarely seems to ever point at a person’s genuine flaws.

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Real intellectual humility is about freely and openly acknowledging when you’re wrong about something. It’s about being precise about what you think you know. Be careful with your words, lay out your thinking clearly, revise your positions as you go.

It’s also important to acknowledge that you will be wrong about things.

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Some people think it’s arrogant to do and say stuff in public because “who the fuck do you think you are?” I think doing and saying stuff in public is an expression of humility, because how else am I supposed to find out the ways in which I’m wrong? What, on my own, inside my own head? With my own flawed thinking?

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Humility isn’t about deference or hiding things from others. It’s about being sincerely mindful of the fragility and fleetingness of all things.

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If you’ve played the Mass Effect trilogy, the character Mordin Solus displays intellectual humility and honesty as he worked through changing his mind about a major plot event. It’s super compelling to witness someone go through this struggle.

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There is humility in accepting that you are an imperfect, unintegrated wannabe, and always will be. There’s also beauty, humour and joy in embracing it.

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Genuine humility is a sense of awe at unknown possibilities.

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since this post is my top search result for honesty, I figure I might as well also include my notes on honesty here.

Honesty

It’s interesting how you can be married to someone and be naked with them and be best friends with them and yet not be entirely honest with one another.

It’s interesting how you can spend a whole lot of time by yourself, with yourself, and yet never quite be honest with yourself…

tweet about how… being truthful can get you marked as untrustworthy, because of the complicated relationship people have with the truth