Jake vs Boss

My friend Jake has a difficult boss. Well, kind-of-boss. They're technically co-founders, but the equity split, titles (CEO vs COO), and age/seniority difference put Jake in the junior position. It's been three years of grinding together on the startup, and this year-end, Jake's boss told him "Look, we've got a money problem. 2026 is going to be a challenging year financially and we need to buckle down. But also, I've worked really hard this year and after running this startup at way below what I think I should be earning for a few years, I'm going to give myself a raise."

"Okay, fine," thought Jake, "seems not great when we need to be frugal, but whatever."

But the next week, Jake saw the actual 2026 budget and his boss' raise, and his heart sank. Jake's boss had allocated himself 75% of the $100,000 reserved for raises. Jake would be getting nothing, and be responsible for allocating pennies to the rest of the team (Jake manages almost the entire headcount).

I was talking with Jake about this, and he said "I need to tell my boss how financially irresponsible this is, and how its a risk to the team, and how (more reasons)... but I just know he won't listen, and he'll get angry in return. How can I change his mind?"

Thinking vs Unfolding

I'll return to the conversation with Jake in a second, but I'll first explain what this post is about.

I want to make clear a distinction between "thinking" and "unfolding."

Thinking is using my rational/conceptual mind to do something: solving a problem, imagining what someone else might think of me, planning a move in chess, and so on. This is often a creative, active process, though it happens passively too, like when the voice-in-my-head chatters and daydreams.

Unfolding is using my mind in combination with my feelings, bodily sensations, and contextual awareness to make progress on the "frontier" of my experience or life. For example, if I'm feeling anxious but don't know why, I can focus on the physical sensation of buzzing in my chest, sit still with it, gently probe it for information, and "discover" its causes.

Answering questions on a high school exam requires a lot of thinking, not a lot of unfolding.

Therapy tends to require a lot of unfolding, not (necessarily) a lot of thinking. For example, my resentment after a bad breakup does not require an "exam-gradable" answer; it requires getting my hands dirty with the feeling, its causes, its consequences, and the full life context in which the feeling keeps arising. I need to "unfold" my stuckness; I can't just think my way out of it.^[1]

Noticing the difference between thinking and unfolding has become an invaluable life skill for me in recent years. It's helped me tune into and learn to trust an "implicit/intuitive intelligence," which has led in turn to a clearer life course.

It has also helped me understand some significant things about life stage development and inner work, which has implications for rationality, spirituality, AI alignment, making-the-world-better, and some other things this community may care about.

I'll finish the story with Jake, add an aside about Jenn's recent LW post, then discuss some of these implications.

Jake vs Boss 2

Jake's situation required unfolding, not thinking.

I said to Jake, "look, I don't think you actually believe that the $75,000 bonus to your boss will make a huge difference to the company's survival. I get the impression that you're feeling disgust and anger at your boss, and looking for some sort of argument that sets aside your feelings and might be rationally compelling to him." He agreed.

We decided to pull on the emotional string a bit more, and the whole chandelier fell down.

It wasn't really about the money.

When they began the company, Jake's boss was clearly his senior, and had done Jake a favour by bringing him in as a co-founder and mentoring him in business. But over the last three years, Jake had improved, become more competent, clearer, confident... and learned that perhaps he was as or more capable than his boss. For the last three years, he'd watched his boss make poor financial decisions, poor hiring decisions, mismanage people, break and disregard internal systems, and generally lead the company from a place of tyrannical anxiety. When Jake had tried to speak up about mistakes in the past, his boss had angrily shut him down. And at this point, the entire leadership team--not just Jake--were concerned that his boss' emotional disregulation and poor business decisions might sink the company.

But we pulled on the string further, and it also wasn't really about his boss or the company.

Jake had grown, over the last few years, not just in his business management skills but also in his inner life. He'd found a way to relax and approach life more playfully and with more curiosity and ease. He knew how to be vulnerable in front of his employees and build trust, and also how to take a holiday and really rest. He'd separated his "spirituality" from formal religion and began to follow a more intuitive path. His sleep had dramatically improved. The company was a way for him to make money but he wasn't emotionally wound up in it, and if it crashed, he'd be fine. But his boss still riled him up. At this point, Jake vs. Boss was perhaps the most emotionally charged aspect of his life.

So what was it about?

As we explored--partially discussing, partially sitting with feelings co-meditatively, following the threads of what felt "alive" and emotionally charged^[2]--it became clear that underneath Jake's disgust and resentment was something like the cusp of a significant life stage transition in emotional maturity and clarity.

Jake was resentful not, ultimately, because of his boss' raise or his boss' historical errors, but because of his own silence in relation to them. Early in his startup days this silence was an appropriate deference, but now that he knew better, his silence felt more and more lack a lack of integrity. By choosing to shoulder "getting through it" rather than risk a difficult conversation (which could potentially lead to the relationship exploding), Jake was overriding an intelligent part of himself--the consequence of which was a type of numbness and foggy impotence that was no longer acceptable to him.

In all other areas of his life, Jake had learned to trust this intuitive intelligence. Much of his growing confidence and wellbeing were built not on top of new hard skills, but on this intuition: he could trust himself as someone capable of navigating reality. And this intuitive path--perhaps something like the Tao--was important enough to Jake that following it was now more important than making money, or staying at the company. And yet here he was: quitting felt like running away from something, but earnestness felt like... (here we sat with what it would be like to say it out loud)... fear.

What Jake really wanted to communicate to his boss was emotionally heavy:

Thank you for everything you've done to help me. you have helped me become the person who I am today, and I am deeply grateful to you for believing in my potential long before I was competent enough to be your peer.

But I am your peer now, and I can see as clearly as you, and you are making mistakes for the company and more significantly for yourself. You are often emotionally distraught and make poor decisions because of it, and that bleeds into the rest of the company. It has bled into our relationship too, and you've hurt me and others emotionally because of it. Trust and communication between us has broken down in ways that I am not sure are repairable, but I want to make this vulnerable attempt to reconnect.

We are at an emotional and pragmatic crossroads. You need to get your act together--not by grinding harder, but by taking responsibility for your wellbeing and clarity. I want to grow with you and improve this company as your peer, but if you don't want to do this, I will need to leave.

Someone else in a parallel situation may have something very different to say. And perhaps in another week, this won't feel like what Jake actually wants or needs to say, or plans to say after iteration. But as we were unfolding it, this was Jake's earnest articulation. It was a level of vulnerability he had never communicated to his boss, and the possibility of speaking it felt out of the question: most likely, his boss wouldn't get the emotional appeal, he'd be shut down, and things wouldn't budge.

But Jake's unfolding here is less about how his boss responds, and more about speaking with integrity in the face of consequence. The opportunity isn't about the money or the company, but about Jake's maturation and learning to trust his intuitive intelligence in emotionally charged situations.

Jenn's Misanthropy

I loved Jenn's Misanthropy post. I found it a hilarious, heartfelt, and earnest exploration of intellectual class and the struggle to love the world as it is. Jenn writes:

For the past year I've been sinking into the Great Books via the Penguin Great Ideas series, because I wanted to be conversant in the Great Conversation. I am occasionally frustrated by this endeavour, but overall, it's been fun! I'm learning a lot about my civilization and the various curmudgeons who shaped it.

But one dismaying side effect is that it's also been quite empowering for my inner 13 year old edgelord. Did you know that before we invented woke, you were just allowed to be openly contemptuous of people?

...

I hold a lot of affection for my inner edgelord, don't get me wrong. But I am also often kind of mortified by her and would like her to be holding the reins like 5% of the time vis a vis my intellectual development, when it's currently more like 20% of the time? 

...

So a few months into reading Freud and Schopenhauer and Tolstoy and Nietzsche, I decided that I should... probably... do something about that? I pondered how to proceed. I assessed my intellectual life, where I was organizing weekly rationality meetups, almost exclusively socializing with people who either had university degrees or were putting out certified bangers on tumblr, and literally reading my way through the great books. And then I had probably the dumbest thought I've had in all of 2025: "maybe getting more in touch with the common man would fix me, since surely that would prove Schopenhauer wrong."

This is some good unfolding. Jenn's following a living thread: wanting to be conversant in the Great Conversation, feeling her way through frustrations, and taking considered action to try to undo stuckness around an over-active internal "edgelord."

Unfortunately Jenn soon finds herself in a difficult encounter with the common man at a local philosophy meetup:

There was a feeling of quiet, growing horror as I realized that people were capable of press-ganging literally any word into acting like a thought terminating cliche. If norms rot away that's just entropy (which is natural and thus good); if things are "subjective" and not "objective" we just have to let it stand (my timid request to define these terms when we were discussing social conventions, of all things, was summarily ignored); one group I was in hummed appreciatively at the claim that a hypothetical was "hurtful" but not "harmful" and I wondered if I had died and gone to hell without realizing.

...

I started thinking: I wasn't asking for full academic rigor, but if none of the other people at that discussion group were at all interested in being critical about the thoughts that were passing through their own brain in any way^[1], then that's... like... sort of contemptible, isn't it?

By the way, if at this point you're like "wow, Jenn's sort of being an elitist bitch here", well, yeah. This was sort of the entire problem that I was here bunglingly trying to solve. But instead of getting fixed, over the course of two hours that night, I Got Worse. I completely stopped seeing the other participants as people with anything potentially useful to teach me, and instead started seeing them as NPCs to manipulate for fun. 

Jenn winds up frustrated, feeling worse after her attempt to engage than before. Though she concludes the post with some equanimity ("Maybe I'll resolve this at some point, but I don't think it makes sense to rush it. Difficult things take time."), she writes in the comments that she's still feeling stuck: "i'm trying to figure out what to do about the contempt. it turns out that when i am around people i find intellectually unserious, i deny them personhood and i act in an incredibly shitty way. my worldview says this is bad and i am sure you agree; my nervous system becomes suffused with hatred and does it anyway."

Holding Love and Comparison

Unfolding is bigger than just emotional processing. Unfolding is also what it feels like to be solving a difficult math problem--but the right one, that's critical for the research agenda you're working on. At the same time that you're making conceptual progress, you're tuning into a felt sense of "why is it important that this is where my attention is going?" Unfolding is telic.

It's kind of hard to do this, and it's a skill that requires, in my opinion, both rationality and emotional maturity. Rationality to do the thinking-clearly part, and emotional maturity to navigate the magnitude of what it means to actually take the world seriously.

If I were in Jenn's shoes, my hope is that a certain perspective on "thinking vs unfolding" would do a lot of work to clear up my disgruntlement at the philosophy meet-up, because being able to see the part of the philosophy meetup where genuine unfolding is happening can bring new life to a situation where the thinking part feels dead.

Indeed, the top-reviewed comment by Nate Showell right now says:

There was likely a midwit-meme effect going on at the philosophy meetup, where, in order to distinguish themselves from the stereotypical sports-bar-goers, the attendees were forming their beliefs in ways that would never occur to a true "normie." You might have a better experience interacting with "common people" in a setting where they aren't self-selected for trying to demonstrate sophistication.

I agree. The "philosophers" in question are likely LARPing philosophy, and ending up with a dry type of thinking. Their words aren't telic. There's no unfolding. The thinking has little "aliveness". They're performative. 

But the performativeness is, nonetheless, important to them. This may not be true for every person there, but I expect that underneath the bullshitty, not-tethered-to-reality philosophy could be fear: a genuine understanding that "yeah, ouch, I actually don't know how to think clearly. I actually am super confused about all sorts of things."

From this vantage, the performativeness is a local-minima. It is an expression of a genuine-not-knowing, and an attempted, unfulfilled desire to think clearly. The inability to listen to Jenn's pushbacks and clarifications (an attempt at grounded intelligence) is a necessary emotional defense to stay in this local minima, as popping out of it would reveal the extent of self-deception happening.

Sometimes you can just rip the door off an emotionally vulnerable situation like this and get to a better situation: honest, rational dialogue, where the gulf in experience is mutually understood. But oftentimes it needs to be done with profound hand-holding and compassion. 

There's vulnerability on Jenn's side too. She goes for honesty in the beginning: playing devils advocate, offering counterpoints... but at a certain point the dismay takes over. At that juncture, unfolding is less Jenn saying "here's why you're wrong," and more saying "hey, pause please - I'm building resentment and loneliness and fear from this conversation because I don't think what you're saying makes any sense, to such a profound degree that my contempt for humanity as a whole is deepening in real time." Not an easy thing to say, even ironically.

So there's two strings to pull on here. The vulnerability of the "philosopher's" attempts to become telic, and the vulnerability of Jenn's dismay. Either of these could be unfolded, but to do so would require mutual trust. The situation heated up too fast, the connection was lost, and the alienation/othering/hatred is what's left.

Jenn is trying to solve a deep thing here: how to hold universal love and comparison at the same time.

I don't know what the exact emotional stack is above/below Jenn's hatred, but here's what mine has been in the past.

Encountering the AI alignment problem, rationality, and the whole shebang has been intense, and dropped a background hum into my reality of something like: intelligence matters a lot; humanity is living in an extremely imperiled era where getting through this civilizational mess requires all of us to be more intelligent and wise.

Having this in the system led to many periods of deep loneliness, fear, and resentment about others, where it felt at times like it's only me and a small number of individuals who are shouldering the situation or capable of shouldering it. The weight/martyrdom of that led to contempt of others, disconnection, criticism.

But I think I've softened around this view--I can feel the nobility of the people I see "really trying" on the hard problem of alignment-- and I can feel the nobility of someone who is working on trying to develop their capacity to philosophise.

One of the great things about the culture in many rock climbing gyms is that, whenever there's someone struggling to finish a route, trying over and over, and they finally make it, everyone in the gym can cheer for them. Their ability level doesn't matter, what matters is the personal surmounting.

Likewise with self-development, intellectual-development, spiritual-development, and so on. Learning to think and learning to unfold are deep, delicate skills for humans to cultivate. And when I can locate where someone is actually trying to unfold--when I can see the part of their action that is telic, intuitive, vulnerable--it becomes easy to connect again, so long as they are open to it.

The misanthropy, the resentment, and taking-comparison-stressfully, at least for me, always arose against the background of my own suffering and fear of consequence, and was a useful string for me to pull on and unfold. 

Hope in the global situation for me comes from a deep belief that the magnitude of the problems we face can catalyze fast internal transformation. That's what happened for me at least, and I think finding ways to help others through the unfolding requires compassion, first and foremost. This position trusts the intuitive intelligence of the other to do the right thing, so long as it is given the conditions to flourish. 

A Few Implications

Distinguishing thinking and unfolding reveals a "path" to me, which I want to gesture at below:

• Most people have a lot of (sometimes buried) implicit intelligence. I get the sense people are often behaving extremely intelligently to the degree they are allowing themselves to be emotionally earnest with themselves. However, lacking emotional integrity leads to bullshitty disconnected thinking that cannot be penetrated.
   
• Getting more in touch with this implicit intelligence therefore requires "unfolding," not just thinking. Thinking risks disconnection, while unfolding is necessarily about trying to zipper-up intelligence and emotional reality, bringing the two into greater accord. This happens situation by situation (as in Jake vs Boss), but also over an entire life trajectory (as in Jake at a more earnest life stage compared to his three-year-ago self).
   
• We need both thinking and unfolding. Some very "intelligent" people can be very dumb, because their intelligence is not contextually sensitive to what actually matters to themselves, or to the world (blocked by traumas and compulsions). Similarly some very "wise" people can lack the intelligence to do things usefully and make progress. They're pointing in the right direction, but treading water. Thus, rationality and whatever inner-development skill I'm gesturing at here are complementary but not the same path (see Heaven, Hell, Mechanics for a bit more).
   

• "Not getting it / not caring about it" can often be the right move for someone, for reasons they can't rationally articulate. When something is not on the "frontier" of someone's unfolding,  they might refuse to understand it, or it can often feel dead to them. For Jake, whose life priority right now is around his integrity and unlocking his full agency, the AI alignment problem isn't salient -- and he's honest with himself about why its not his main focus.

  One can try to make something emotional salient to someone in a rational way, and some people update like that, but intuition-based updating is often what I think is happening for people. Rather than being a logical update, it's deeper, emotional, relational one. It is not arguments that eventually convince sometime to care or work on a problem, but rather building a tether between the frontier of their intuitive intelligence and the problem.
   

• "Getting it" becomes harder and harder the more challenging the emotional hyperobject is. Given that the AI alignment problem -- and the cluster of related issues around the metacrisis or whatever else we're looking at together -- is about the heaviest emotional hyperobject one could imagine (at its center of gravity is Death, Immortality, and the other big dawgs), its reasonable to expect that people without the emotional capacity to hold it will bounce off (there are other reasons, like shock levels, but these too are emotional-logical)

  And often this can be intuitively intelligent, even if it looks irrational: if something is going to be emotionally devastating to the point of collapsing a listener, it is good for them to avoid it!

  My experience with getting into AI alignment was a process of at-first-not-being-able-to-handle the hyperobject, suffering a lot, but that exposure eventually making me clearer, more capable, happier. However, I've also seen cases where it has led to excitement, then overwhelm, then stimulant use, then burnout, then addiction. This is not light territory.

  Because of all of this, I think it is continually important for the rationality community to be vigilant about the emotional/psychic dimensions of this work, and embody greater compassion in our communication to others about the subject (e.g. a politician may bounce off the subject for a number of reasons, but one of them may be: if they genuinely incorporated this view, and took it seriously, it would complete unwind their entire life and career. No wonder a single meeting doesn't compel them -- though sometimes it can too!)
   

• Inner development as a path is important, and requires unfolding, not just thinking. Increasing emotional carrying capacity cannot often just be "thought" towards, because it is not purely conceptual. E.g. AI can give you meditation instructions, but it cannot meditate for you: only you can "do" the inner work and move your mind.

  Therefore inner development and life maturity are not purely about rationality. The purely rational path may work for some, but I've seen far more cases in the rationality community of people who are ignoring their vulnerable earnest intuition (the voice that, following it, may make them stronger in a new way) than I have the pure-head types who can do it through reason alone.

I love "unfolding" things with people, and being on the edge of personal and technical progress. But sometimes it is also not the right thing to do. There are times when mundaneness is the right thing, and there are times when just being silent and appreciating it all is the right thing. The urgent need to unfold, all the time, communicates both a deep love for the world, and deep criticism of it. I find it nice to hold both, and sometimes neither.

1. ^{^}

   Less "therapy"-like examples of unfolding include things like earnest debate, intuitive dance, unconferences, circling, active imagination. 

2. ^{^}

   There's resonance with "focusing" here, but I don't think of unfolding as an activity like "were going to sit down and unfold now," I think of it more as a type of earnest, embodied thinking. It's a mode of engagement rather than an activity.