For what it's worth, your struggles with modeling others via ToM probably had very little to do with your interest in Objectivism, individualism and the like. It seems that many, perhaps most children and teenagers share this trait in the first place; moral development is a slow process, even for those with entirely normal emotions and a normal substrate for affective empathy (i..e the non psychopathic/ODD/ASPD!).
I do have to caution though that the basic other-awareness that being non-psychopathic gives you also makes you a lot more effective at modeling others' preferences and being able to enter into efficient win-win deals and arrangements with them. Renouncing that other-awareness thus has very real costs, while OTOH the benefits of doing so are quite dubious. After all, even though you're obviously self-interested in some sense, you aren't trying to pursue the same preferences as a psychopath/ASPD would. And when you say "I’m able to constrain others rather heavily" by doing this, you're probably fooling yourself since expectations, implicit demands and social constraints are inherently a two-way street - they empower you to influence others even as they act as constraints on your own behavior!
I've found I've become much happier as I honed my empathy while minimizing the assumptions that I make about others.
I'm pretty convinced that none of us really understand the vast majority of our own motivations. It therefore feels doubly useless to worry about that in others. It's better to just have a theory of behavior when looking at people most of the time. It allows you to really understand how others feel when they are just as lost and confused as me.
It's listening and communication over modeling. When someone tells you how they feel, just fullstop take them at their word as any starting point in modeling. It's a lot easier to like people this way, and it negates most fights.
Most fights come down to, "you're just not listening to me, damnit!" When you actually do that, and then show caring and compassion, it means most fights last minutes and never get intense.
Listening is caring.
This would make a lot more sense with some examples of what it means to fail to "mark most significant personal information about others as salient, unless I'm explicitly told to keep it in mind."
Some of what you describe (specifically when you mentioned theory of mind) seems to me like the asperger syndrome.
If you want to understand others better, and potentially learn empathy, consider active listening. 7cups.com and a couple of other sites have a bunch of useful guides and you get to hear out real people opening up about their issues.
> But then again, maybe the reason why I don't like most people and find them shallow is my lack of empathy, so the causes and effects might be tangled up here.
http://agentyduck.blogspot.com/2015/05/tortoise-report-3-empathy_16.html
A good read for anyone who thinks they might have that problem (which was my problem up until about two years ago)
One type of the more common accusations that people throw at me can be described like this: "You're an egoist. You don't think about others." To my teenage self this sounded amusing, and I would respond with a smug "Why yes, I am an egoist, thank you very much!"
Here I have to make a confession: back then I was pretty much obsessed with Ayn Rand's Objectivism. For those who don't know much about her philosophy, it's a flawed attempt to create a consistent philosophical system that covers just about everything, from ontology to aesthetics. It has very stark individualistic, libertarian-ish vibes. Being a naive yet curious kid, I was enamored with what turned out to be my first expose to (relatively) rigorous argumentation, logic, and philosophy/critical thought in general. I can't thank Rand enough for that, because through her I encountered the concepts of reason and rationality, which in turn led me to LW, The Sequences and everything else which formed the basis of my mature thought.
Anyway, after a while I moved away from objectivist ideas. I clearly remember the "final nail in the coffin" moment. I was rereading THE SEMINAL WORK THAT SYSTEMATICALLY EXPLORES AND DEVELOPS THE IDEAS OF AYN RAND, particularly the part about the consciousness axiom. I remember thinking: "Wait, the assumptions that the argument lies on are completely unfounded, what the hell is this epistemology LOL". That was it. No dramatic catharsis-like moment, no nothing, just the feeling of having finally checked off an item from my bucket list.
Despite my going through the rejection ritual, a lot of moral intuitions that I formed in that period carried over into my new, semi-adult life. I shunned social norms and laughed at those who had to conform. I prided myself on being socially brave, freely asking people for favors and being able to take a rejection and reject myself, giving compliments left and right whenever I felt like others deserved them, expressing myself authentically, without fear of judgement or public shaming.
Most of this was connected to the classical-liberal-ish notion of "anything's OK as long as it's not initiation of physical force" and its corollaries, coupled with intuitions like "nobody owes nothing to no one, thus e.g. asking for favors is totally OK and even good (cuz self-interest), but only if you're able to take a 'no' for an answer; we all are free people after all" and others from the same neg-lib-and-egoism cluster.
Plot twist. This Randian experience left my empathy in a stunted, primitive state. It's not on the levels of psychopathy/ASPD, I experience rich emotions, can empathize with others (both affectively and cognitively), my tracking-social-cues mechanism works fine, I'm able to enjoy fiction, etc. But my brain doesn't mark most significant personal information about others as salient, unless I'm explicitly told to keep it in mind. This means that generic social rules and explicit agreements work fine for me, but many implicit expectations are bound to fall short, because the necessary personal information about others' preferences just doesn't jump to my mind whenever I'm making a decision that can affect some other person that's relatively important to me. Of course it's more complex than this, so please remember that I'm painting in broad strokes here.
This fucking sucks. I do actually feel remorse every time I unintentionally hurt someone, it's pretty horrible, almost every time I wish it didn't happen. It's usually not an issue with acquaintances and friends, i.e. we're not close enough, so they end up getting hurt by me very rarely, if ever, but at some point if you want the relationship to progress, you have to be able to count on the other person to take on some of the responsibility for your well-being. That's how you develop trust, which is an important prerequisite for vulnerability and sustenance of long-term cooperative relationships. To be responsible, you first have to become aware.
Which is exactly where my bottleneck lies. I don't model others well enough, typical-minding aside. Or rather, for some reason I'm disinclined to do it. It feels like a burden. I want others to tell me what they want from me, explicitly and precisely. That's how I operate myself. To me it feels like taking personal responsibility for your needs, which is Good. Actively taking responsibility for others feels Wrong, because what the hell, why am I supposed to do something for them? No one owes me anything, but neither do I!
Now, I do exhibit caring behavior, sometimes, towards certain people. It feels good and authentic. That's because when I do it, I really value the person and want them to be well. One confounding factor could be that I simply don't like most people, they're not "good enough for me" in my eyes, so I (read as "my brain") don't care about them enough to model them sufficiently. But then again, maybe the reason why I don't like most people and find them shallow is my lack of empathy, so the causes and effects might be tangled up here.
Several broken relationships and lots of pain behind me, I'm dating someone again. I'm different now, having studied a lot of psychology, philosophy, basically everything human nature. I'm stronger. And, as it happens, this relationship is much healthier than others, it spurs a significant amount of personal growth, despite the short time span: patterns become obvious, small yet meaningful change takes place. I'm thankful to my SO. Even if our paths diverge at some point, I've gotten a lot of value out of our relationship, and I hope so did they!
First off, let's start with the belief/alief dichotomy. Here's my daring and frivolous interpretation: Beliefs are about meticulous calculations, S2 override, and social interfacing. Aliefs are what drives your S1 by default, affecting greatly your motivations and behavior. It's important to be able to explicate aliefs, because that gives you the opportunity to intentionally change them. They do change on their own, of course, but it happens more or less randomly, subject to the chance workings of environment, experience, and reflection. Lots of so-called internal conflicts -- procrastination, negative spirals, self-loathing, etc -- are the result of identifying too much with S2, the mind, and not enough of "accepting" S1, the body, as a part of your self-concept, or so I think anyway. Cartesian delusions are crappy at modeling reality, but sadly are pretty intuitive and thus quite widespread.
But I digress.
Stripped of all ethical chaff, I unearthed an alief. It goes like this:
"Freedom from social constraints is good. If I let myself become sufficiently aware of others' preferences, this will turn me into an anxious self-conscious nervewrack and I'll lose all the benefits I'm reaping from my current attitude"
The concept of slack ties into this very well. For those who want a quick refresher, something something our behavior is partly managed by the expectations and implicit demands of other people. This post by Val is probably relevant, too.
I have lots of slack. What's more, I'm able to constrain others rather heavily, e.g. by openly signaling my preferences. I'm allowed to do this precisely because I'm less attuned to what others prefer. It's a strong, honest precommitment mechanism: if you're not even consciously aware of the fact that you're thwarting someone else's preferences via action, you pass the internal-S2-self-policing-social check; after all, none of this was intentional! This lets you keep your self-esteem safe and sound, and thus lack of adequate punishment perpetuates this behavior further.
You could say that my S1 values my slack so much that it's afraid to even look into the minds of others, aside from barely scraping the surface. There's no going back after tasting the forbidden fruit. "Yes, you're naked and ashamed, boo-hoo, go cry me a river, and fuck off from Heaven while you're at it" -- God, probably.
Already noticed the mistake I'm making? No?
Well here it is:
If a person who has no ToM gets suddenly struck by Insight from Above and gains the ability to See the Other, they'll ebb-and-flow between very unpleasant states of panic and less-but-still unpleasant states of confusion and disorientation. They didn't have the privilege of gradually easing into social reality and slowly mastering aspects of peopling, and reality hit'em like a brick. Being aware of the enormous pile of demands and expectations without knowing exactly what they are must feel like, I don't know, doom.
However, it mustn't stay so. If this newly-baked Seer survives the initial shock, they'll start developing better and better mental models of other people and accumulating useful heuristics. The Art of Prediction will get honed and polished with a zealous striving for perfection.
Now that the initial dip in effectiveness is persevered through, the Seer finds that their life has become much better, being able to subtly navigate between the streams of social information, manipulating these flows to their liking, enjoying the ever-increasing benefits of social aptitude, the sly beast!
Anyway, here it is. Only thing left is to feed experiential evidence into this new reframe, which requires crashing into reality, which can hardly be done by putting more words on the metaphorical paper.
So I guess I'll go out and do just that.