Why The World Doesn’t Want You to Succeed (and What to do About it)

High. Dangerous. Long way to go

Truth one:

“Our days are filled with the path to future skills, tasks and commitments that we believe we can’t possibly take on. We’ve seduced ourselves into believing that we’re not born with the talent, or that the obstacles to doing the work are just too great.” —Seth Godin


Truth two:

“Attempting [to have a huge positive impact on the world], would be immodest. Because it would be immodest, the world will find a way to strike you down. They won’t let you get away with that. It will make this blow up in your face. And laugh. At you.” — Zvi Mowshowitz


I want to have a huge positive impact on the world.

At the same time, paradoxically, I feel what I do for a living isn’t good enough. I’m ashamed. When someone innocently asks how I spend my waking hours, I panic like I’m forced to expose my darkest secrets.

If you go the ambitious route, how do you answer the voices — not least, the voices in your own head — that call you arrogant, hubristic, even a potential crackpot?

You’re coming in in the middle of a fictional session with my fictional psychotherapist Henriette.


The Hammer and The Nail

Henriette: You know Maarten, I’ve been listening to you talking about yourself for three hours and eighty-three minutes now. It seems to me that what you’re doing here — you’re beating around the bush. You’re avoiding the real reason why you feel ashamed of yourself, your essays, your job, your opinions.

Maarten: Let me guess —

Henriette: I’m not going to mince words here. How much did your mother love you?

Maarten: Well —

Henriette: You’re afraid to express your opinions, especially if they have a normative dimension. “Who am I to tell people how to spend their afternoons, how to disagree, what their real job is, and so on?” You’re afraid that, if people were to know that you’re that kind of annoying person who has all these normative thoughts on how they can live better and how society could be better, people would not love you. They’d think you’re arrogant, committing a status violation.

Maarten: I wouldn’t put it in exactly those terms, but yes.

Henriette: So who exactly are you to claim there’s something worth trying? Who are you to claim you know better than everyone else? Did you not notice all the other people? Are you really high status enough to claim you know better than all of them?

Maarten: I thought you were supposed to be on my side.

Henriette: (proud) I recently did a Zen Mindfulness Yoga Soul Cleansing Also Charka Karma And Heal Your Spirit Buddha Is Big retreat and I have discovered my Inner Me so I’m doing a new style of therapy now.

Maarten: (rolling eyes) … Sometimes I wonder who’s the therapist here. Anyway, yes, I get these voices scaring me into thinking people interpret my self-improvement blogs and political writings as implicit accusations.

Henriette: Haven’t you admitted you’re prone to experience the occasional existential crisis? That’s evidence something Deeply Psychological is amiss! Let’s talk about how you fear the silence of existence, dread boredom and run from the problems of your emotions into the false comforts of intellectualization. You embrace busyness so you don’t realize you are bored when you are running from one place to another.

Maarten: I see where you’re coming from. Some of my favorite fictional characters cite avoiding boredom as the reason why they do what they do. Castle in Castle, Shawn in Psych, The Joker of course, Lucifer in Lucifer, and Barney in How I Met Your Mother. Their behavior is related to the type of Soul Trouble you’re suggesting —

Henriette: In your case, it has to do with your mother, and your great great aunt Petunia is also involved somehow.

Maarten: — However, for the first time since I noticed this years back, I now believe another hypothesis explains the data — my shame, my anxieties about talking about what I want to do with my life, and my fear of rejection — better.

Henriette: Almost everybody thinks of themselves as self-aware. They think they know how they feel and what they want and what their problems are. But the truth is that very few people really do. What makes you think you are any different? Per the Dunning-Kruger effect, most people mistakenly assess their abilities as greater than they are. Hence, let’s just assume you’re not some kind of super genius who is in a reference class of his own. That would be arrogant. And a status violation. So, about Petu —

Maarten: (angry) Will you please stop recasting all my claims as status claims about what kind of person I am?! That inference is precisely one of the causes of the problem.

Henriette: (holding back a tear) You’re finally showing some emotion with me! This is progress!

Maarten: (letting out a deep sigh) … Anyway, here’s the alternative explanation for the uncertainty I sometimes feel about my own value. It has two prongs.

Henriette: Did someone say intellectualization?

Maarten: One: I’ve been assuming what we might call ‘civilizational adequacy’. I’ve been presupposing general real-world systemic competence. The voices in my head were like: “Evidently our systems function well, and if I reckon they’re full of mistakes, surely that means there’s something am not getting? And undoubtedly authoritative institutions have good reasons for their actions I’m too blind to see? Certainly that person knows what he’s doing? Surely he does too? And she does too? Who am I to make all these normative claims about how things could be better?”

Henriette: Yes, social consensus ought to be respected and you can’t even grow a beard. When you spot that much room for improvement and attempt corresponding interesting things in the future, you should conclude you are both wrong (things are the way they are because that is how things have to be) and arrogant (you shouldn’t associate yourself with an image of possible future success above your current status).

Maarten: Yeah, the thought continues: “I feel like I’m right, but most people in the same situation, people who also insisted on their mental competence even if it went against the way most people did things, were wrong. Their “critical thinking” leads them to kill their own children because they refuse to vaccinate them. In light of that, it might be wise to reject your intuitive feelings of rightness and assume you are probably wrong too, tiger.”

Henriette: This sounds like a fine assumption to me. And thinking you could do better, and tell people how to read, or that education is broken, or how to live, would be overconfident (boy, you really are fond of making normative claims). These “Who am I to …” voices in you’re head are perfectly justified.

Maarten: You just perfectly illustrated the second ingredient in the alternative explanation. Society frowns upon immodesty. Sadly, human beings are status comparing machines. If you attempt something immodest, the world will strike you down. Grown-ups, in a devastating example of good intentions gone baddiscourage challenging the status quo. They tell their children how they are not very special, probably can’t do the special thing, and will fail if they try. “Sorry, kid,” the older person says as he smiles with gently forgiving superiority at the youthful enthusiasm of those who are still “naive” enough to attempt to do better.

Henriette: So how does [civizational adequacy: the way most people do things is probably near-optimal] combine with [no-immodesty: trying to do interesting things in the future is a status violation] to explain your shame for (i) claiming how we can do things better and (ii) striving to do so?

Maarten: Seems to me you’ve connected the dots pretty well there. Per civilizational adequacy, I was instinctively assuming that there was something off with me because I figured a social consensus was wrong. Per no-immodesty, every time I was thinking I could do better accordingly, I thought I was revealing my own ignorance and arrogance instead. Hence my shame about it. The shame is a to-be-expected consequence of the situation, not a sign of Profound Soul-Crunching Issues.

There was a pause as Maarten felt he was done and Henriette was absorbing all this.

Henriette: I still don’t see what led you to discard your assumption that the social consensus is probably right, and you are probably wrong.

Maarten: The book that made me change my mind was Inadequate Equilibriaby Eliezer Yudkowsky. In it, Yudkowsky first takes a look at how a social consensus actually forms. Turns out there are a lot of holes in this process. Our experts don’t try with their full efforts to solve your personal problems, but instead, try to win the world’s somewhat arbitrary games. In many cases, one can see plausible system-level problems that could lower the quality of ‘the way it’s done’. In other words, there exist what economists call “agency costs” and other “market failures” that result in “inadequate equilibria”. Therefore, it need not be irrational to trust your own conclusions when they deviate from the norm.

Henriette: Is this anything more than mere theoretical abstractions? Are there actually many “inadequate equilibria”?

Maarten: Yes, there are. We really, really don’t live in a Totally Optimized World where self-questioning would be appropriate if you dare to think you can reach an above-average percentile level, as is implied by the “Who am I to think that I …” argument.

Henriette: Before you offer concrete examples I continue to ascribe your large collection of diagnoses of room for improvement and ambitious plans to your ignorance and arrogance, not to systemic incompetencies. There is something inside you we need to fix!

Maarten: Systems can end up dumber than the individuals in them due to multiple layers of terrible incentives. Whether you should throw away your own opinion in favor of social consensus depends a lot on whether that giant institution might fail in some unexpected way. I’ll give you three examples.

Henriette: This is going to be funny.

Maarten: Science is broken, with scientists and grantmakers doing a bad job of focusing their discoveries on truly interesting and important things. Health care is inefficient and costs way too much. And, finally, Malcolm Gladwell has said: “When I’m writing about something, my assumption is that almost everyone who has written about it before didn’t do a good job. Pick a famous court case, and read the popular press about it. In 98% of the cases, you’ll discover that the people who wrote about it didn’t actually attend the trial, read the transcript of the trial, or interview anyone. People are lazy.” Now, when Gladwell casts his verdict about “almost everyone”, do you think he is speaking from experience or being misinformed?

Henriette: It seems to me that, if you’ve discovered the emperor isn’t wearing any clothes while everyone thinks he is, you can say “holy shit,” pardon my French, “everyone in the world is insane. However, none of them seem to realize they’re insane. By extension, I am probably insane. I should take careful steps to minimize the damage I do.”

Maarten: I’ve got to say I love your supportive attitude. It seems to me you’re asking the wrong questions.

Henriette: (confident) I didn’t even ask a question. Haha!

Maarten: When doing adequacy analysis, it’s important to treat the question of whether you could be more competent than some aspect of society as a case-by-case question. The fully general argument you’re making overlooks that we can go too far with doubting the role of individual reason in a world that “stands on the shoulders of giants”. You’ll start accidentally proving nothing can be bad anywhere.

Henriette: You’re missing the point. As you probably know, there’s something called ‘Wittgenstein’s ruler’: unless you have confidence in the ruler’s reliability, if you use a ruler to measure a table you may also be using the table to measure the ruler. The less you trust the ruler’s reliability (in probability called the prior), the more information you are getting about the ruler and the less about the table. Unless the source of a statement has high qualifications, the statement will be more revealing of the speaker (your ignorance and arrogance) than the information intended by him (there being an “inadequate equilibrium”).

Maarten: It’s funny that you pull status-considerations back in the picture and lecture me on probabilistic reasoning. From that perspective, when should you trust social consensus? When should you trust your own reasoning? My giant realization was that the shame was a normal consequence of the situation, and therefore not onto something about how I was ignorant or arrogant. It need not be crazy to hold on to your conclusions when they imply, for example, you can outperform 98% of people who have written on a given thing before. Whether doing so is rational in a given case or not, of course, depends on whether certain conditions hold. The fact that it is an open question whether they do, shows that believing you can do better than most people on a given thing doesn’t automatically merit “who am I to…” voices in your head. The asymmetry could be the other way around.

Henriette: I’m not sure I get it.

Maarten: (excited) Don’t you see? When some whole process seems pointless, you’re brought up to think that means there’s just something you are not getting. This is reinforced by how society heavily weighs relative status in determining odds of success. How it responds to overly ambitious plans as though they were not merely imprudent but impudent. And how it privileges the hypothesis that authoritative individuals and institutions have mysterious unspecified good reasons for their actions, even when those reasons stubbornly resist elicitation and are sufficiently explained by misaligned incentives. However, since social consensus isn’t that informed, having many disagreements with it is perfectly possible without me “knowing better” stemming from my own ignorance or arrogance. The same for concluding you can reach the 98th percentile on something. High-status systems can actually function badly, and you can improve them.

Henriette: And if you go that route, how do you answer the voices — not least, the voices in your own head — that call you arrogant, hubristic, even a potential crackpot? That want to strike you down?

Maarten: (talking loudly and quickly) The “Who am I to…” voice is insidious. It says whatever it has to. It lies. It cheats. It is the opposite of useful. Some such worries about social disapproval are legit. But they’re mostly trying to halt you thinking for yourself about the object level, to keep you from being the nail that sticks up and gets hammered down. When someone else raises them, mostly they’re the hammer. The fears are mirages we’ve been trained and built to see.


After a long day, Henriette sat down to process her notes. She wrote: patient is still insane. Illusions of grandeur are only increasing. How can he possibly be so overconfident as to dare even try to have a huge positive impact when most people don’t even come close to that?


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