“Egy középkormélyi theológ - gondolhatta, gondolom - (nem skolasztikus talán - ki üvegből fújja várát színtelenre - hanem kinek üveget fest lelke szennye - kinek minden régi szó egy régi kép - testi misztikus talány - mert az eszme hűs, átlátszó, tiszta, színtelen üveg - s csak a test a misztikus, vak, s szennye szín és bűne szép) - egy ily ős poéta-doktor: nagy palást, tanársüveg - bájos régi doktorom - gondolhatta, gondolom - úgy mint én diákkoromban…” Mihály Babits
“I dare you to get close enough to me that we both change.” Toby Shorin
During the first two weeks of October, I was working on a piece about strangers for this blog. I have a lot of thoughts about strangers. I think America has a “stranger culture” which I find quite unique and fascinating. More on this later.
Then mid-October I found myself in San Francisco and in a series of conversations with friends, who made me realize I first must write about people who to me feel like the opposite of strangers. The characters who inhabit my life and, through our adventures and attachments, actively shape it.
I am mystified by the opposite of strangers, and how one becomes one. Why is somebody not a stranger to me while another person forever remains one? How does that connection — that curation — work? How much free will and say do I have in the matter? Are the characters in my “plot” somehow preordained, pre-written, and I just have to meet them at some point? They were always there, just waiting…? Or are they innocent bystanders that I choose myself and then try to “convert” into a connection? How do I know if we are truly connected? … How does anybody know anything?
Maddening.
I also found out that two friends whose takes I value greatly are writing books, respectively, about mentors and muses. Uh oh, I thought. Uh oh! If even they don’t know, then we are truly screwed. Why else would anybody sit down and write a long-ass book if not because they too are so mystified and troubled by this that they have to spend hundreds of pages trying to figure out what is going on!
And so it seems like despite everybody’s best efforts, some of the most important relationships in life have remained mysterious. Because it is, still, a mystery indeed why certain people move and affect one another — while some others remain untouched. The media can eulogize the Human Relationship (R.I.P.) all they want, the moving and affecting are as strong as ever.
I generally don’t like writing about people who are important to me because what if they get offended, or too flattered, or run away?! So I decided to approach this question like it wasn’t really about me, as if I was just an observer. The Fool in the medieval court following the comings and goings of potentates from the foot of the throne. (Aren’t we all, anyway —)
My goal here is not to come up with some all-resolving formula; I just want to think through this stuff in public. I want to sit and watch the master builders and tradesmen, the poets and the priests, as they strut and fret, and tell you what I have seen. Most likely, it will signify nothing.
Mentors and muses are a great starting point for meditating on important relationships because these are both relationships that are complex and unfair, both timeless and also very loose and fickle in structure. When things are simultaneously important and confusing (see: people), our negotiations will be vigorous. These relationships must acknowledge their being relationships in the first place — as opposed to some kind of drive-by transaction — and then build themselves from the ground up, from first principles. Bildung.
As they are being built, we get to ask our questions.
Every question a person asks about society is, at the core: How do people work?
And every time we ask “How do people work?”, what we’re asking is: How do I work?
No one ever feels like they know enough about themselves — or, as it follows, about each other.
So let’s look at some less obvious ways in which people are not strangers to each other — and, thus, to themselves. There is nothing stranger in this life than the familiar.
*
Some languages, like French, use the same word, “stranger”, to mean “foreigner”. In English, too, we used to say — pre-science fiction — “alien”. It is preserved in bureaucratic language, for example, how my visa says I am an “exceptional alien” in America.
Exceptional or not, the foreigner is always an outsider. There is a lot of knowledge that comes with this outside perspective. Not all of it is comforting or complimentary.
When we talk about outsiders becoming entrants, we’re talking about an entrance into a society. New people can only enter new circles when they are invited. The best way to get invited is by a member of that circle whom the other members accept and respect. These are often seniors within the circle, some even in leadership positions. When a respected senior member introduces a newcomer, the newcomer’s entrance is seen as legitimate. We trust the judgment of senior people more because they have seen a lot.
When this entry is professional, a great person to be invited by is a mentor. Joseph Campbell — or George Lucas — will have you think that mentors materialize like some kind of interlude on a lonely Hero’s Journey; that they ride in having turned all white and shiny to help you when you think all is lost, and then are gone. This is not how mentors work in real life. While muses might respond to invocation indeed, in real life a mentor is an invitation.
In more ritualized spaces — from some workplaces to frat houses — these invitations follow specific rules. In the more self-arranged, “weirdo” worlds of tech, the arts, or big city subcultures, these rituals are harder to concretize, it’s often something entrants and mentors have to figure out individually, for themselves.
It is because of its undefined structure and how under-explored it is that there is something about mentorship that can be revealing about how all human relationships and communities — ethics — work. There is something crucial to be learned here on what matters, what we owe to each other… etc. Why such relationships can have such a seemingly outsize importance to people. Why succession crises feel like life/death. The ever-present anachronisms of social and sentimental life that we’re losing our words for.
Mentorship indeed can feel so high-stakes because it is tied to the complicated matter of social acceptance. We assume our physical and psychological selves evolved for a prehistoric society where the survival of individuals was a group task, and so social acceptance would determine whether you would — for real — live or die. Maybe “overreacting” matters of acceptance and rejection is not such an overreaction after all.
I think this is important, but doesn’t give us the full picture. The thing is that mentorship is shockingly under-discussed considering how life-changing its impact — both immediate and longterm — can be. This impact is in fact much closer in range and size to that of romantic commitments or child-bearing than to everyday level collegiality or adult friendships.
As with romantic attachments or fertility decisions made for one’s family, mentorship can change basically everything about your life: your life plans, your self-image, your career, your circle of friends, your financial situation, your marriage prospects, which country you live in. These are not trivial matters. And these great metamorphoses take place in these extremely under-regulated, low-orderliness spaces — Patrick Collison calls it “under-theorized”; I call it primordial intellectual chaos — where the boundaries are truly only defined by the sympathies and decency of the participants, their judgment and good care.
It is all the more interesting how, and you will read more about this in a later section, in a lot of modern-day cases people will only speak to their mentor once or a handful of times all their life. (Sometimes never directly!) If you have ever hopped on a mentorship call with a younger person who then seven months later phoned you out of the blue from a new city saying: “I did what you said; I quit my job!”, and you are absolutely sure you never said anything like that to her during that one meeting where you ever spoke to her, you will know what I am referring to.
I think the elemental, nuclear-power self-creativity that is activated in mentorships is both exciting and scary. No wonder I paired it with the Muses. No wonder society likes to pretend it … doesn’t exist.
So I will risk sounding like a Fool and say: it does exist.
On my own journey, I am exactly midway right now, just out of the forest. I am both a mentor myself now, and in some sense still being mentored by others. So I think I can report from the trenches in between. Maybe you will find it useful.
*
Despite a deluge of self-help books promising otherwise, to most people self-creation is a source of shame. When it comes to how smart we are or how great we look, we like to act like our success works like the dreams in the movie Inception: no one really wants to remember how it started. You want to seem like you were dropped into it in-medias-res. (Or, to be more accurate, in-social-medias-res.) Born this way, woke up like this…
This is why people alter the story of the formative years of their careers, or how they really made their first million, or how they really met their husbands — this is why people delete old photos from their online profiles.
Since mentors represent the beginning, they necessarily enter people’s lives at a time that people will later remember as embarrassing. The first thing good mentors show their mentees, therefore, is tact. Good mentors also tend to have a good sense of humor. Tact and humor help mitigate the fact that they have just walked knee-deep into someone else’s suffering (or at least self-doubt and dissatisfaction).
All human relationships are about information. We want to attach to and then exist in information systems, and are drawn to people who we feel have important information about us. We then try to both stabilize how we can continue receiving this information and share our own, and we try to manipulate how positive the other person’s interpretation of us as information is so they don’t cut us off. Fun!
In good relationships, the learning is mutual, an exchange — of notes about the Other, the self, the world. (“How does the world work…”)
In important relationships, the information we think the other person has about us is vital. We feel like we can’t go on with our lives without knowing it. Every romantic couple thus becomes a self-fulfilling prophecy: the parties feel like the other person has such deep insight into them that they then end up sharing a lot of personal things with each other that they’d never tell anyone else. In families, the information channels can get blocked which causes unhappiness: since the reality of a family always to some degree rests on nothing changing, individual information updates can be rejected or ignored.
The information exchange that takes place in mentorship is just as existential: it is about a person’s self-creation. A lot of things at the beginning hurt. Good mentors can both soften the blows by providing counsel and community, and show — through their own example — that there are later stages of this journey, and that it gets easier.
The truth is it doesn’t just get easier. I personally have never felt such sheer abundant joy and professional contentment — such hope — as in some of these collaborations. And so, despite the darker side, which we will also discuss, I will begin with this:
Joy
There is a time in the Jewish calendar for pretty much anything that can ever happen to a person, and so there is a time in the Jewish calendar dedicated to thinking about joy.
The Talmud gets my timidity of writing about something as personal as mentorship: the Jewish tradition understands that joy is a very fragile, very personal, embarrassingly intimate state — much more so than sadness which is always universal, always somewhat public.
Sadness is given to us by life; happiness is an individual achievement, a marriage of internal capacities and external conditions. And so it comes with the state of joy to be very afraid of losing it.
This means in joy we are quite vulnerable. There is a therapy-led misunderstanding that great relationships exist to save us from pain or help heal our past traumas. I think it’s the other way around. Strong relationships in fact are tasked with containing our joy — this uniquely disruptive emotion filled with childlike abandon and a very adult fear of loss — in which we stand most vulnerable.
The fact that an event as sensitive as people’s moments of self-creation — one’s professional birth — permits the presence of good mentors, that even such a fuzzy human arrangement can contain something this momentous for another person, proves to me that indeed real mentorship is one of the great relationships in life. That the intuition and desire to exchange information this way are warranted and can be fulfilled.
As I am typing this, I wonder if mentors, whose effect seems so robust, are only “mysterious” and fuzzy and hard-to-define in the modern sense — that they’re in fact a resurrection of earlier forms of human organization, that they work in a way our current society just doesn’t have a good vocabulary for.
The Fool will know.
*
Whenever I run into a confusion of concepts, I like to look at what other languages are doing about it. When I do this about mentors, I immediately realize that my mother tongue, Hungarian, doesn’t traditionally use this word at all. We do use “to mentor”, the verb, but for a person we use “mester” (master). In Hungarian, there is no secondary meaning to this word as “lord” or “owner” at all — the master is simply the guy who in a medieval town would be the senior blacksmith or carpenter, a master of practical skills leading a business and taking on apprentices whom he would initially train, then collaborate with, then make his heirs.
The secondary meaning of the word that Hungarian uses is artistic and spiritual. It is there in English too, consider the maestro, or the author fighting the Devil in The Master and Margarita. Recall the Zen master in the koan who refuses to come out of his cave until his disciple outside has reached enlightenment… Master Yoda… Or ask any chess player what “grandmaster” really means.
There is a useful pointer in this practical-spiritual double-entendre: medieval society, which in many ways was much wiser than our own, understood that matters of the hands and the soul are both forms of expertise requiring invitation, guidance, and graduation. That the difference between inner and outer forms of expertise is illusory.
In the long centuries when archetypes roamed the world, when tarot cards and astrological signs were just town jobs, when the stakes of life were very visceral and very obvious to everyone at all times, when people sought to be useful and good because they believed in judgment after death — which was frequent and soon and everywhere — people understood that acquiring and utilizing skills, whether religious or dexterous, were matters of the soul.
That what really was at stake was your soul.
Towns have changed but people have not changed a bit since then.
In languages where mentors are masters (who may or may not also choose to mentor, as a verb), it is implied that one can graduate from masters.
While “mentorship” may feel goalpost-moving and fuzzy, mastery implies eventual independence — shared work, equality, possible friendship. (The Master is not a master to Margarita.) It promises shared joy in shared obsessions. It promises shared possessions.
And so if you find yourself confused about how modern-day mentorship works and why in some people’s lives it is a baseline-defining experience, just think of it as a medieval morality play: Experience introduces Virtue to Youth… Wisdom wants to give long speeches. Joy comes in and knocks everyone on the head. And Death suddenly looks less spooky.
*
If you want to go even deeper in history, Confucius is another good place to stop. Those guys knew a lot about professional advancement and how it all was in the end a spiritual process. How all manual or mental expertise was meaningless if you strayed away from the Way, if you denied your soul.
In the Confucian philosophical guide I Ching — a great example of systematized mastery intended to help real-world decision-making — after many images of approach, learning, breaking through, and following, one arrives to the image of The Lake (which is also called: Joy).
This symbol (58) is of two lakes connected and replenishing each other so neither will run dry alone. It is also the symbol of talking, of conversation:
“Lakes resting one on the other:
The image of the JOYOUS.
Thus the Superior Man joins with his friends
For discussion and practice.”
In the I Ching’s intelligent cosmology — from which Leibniz deduced the binary system and invented information theory — it is understood that ‘“Superior Man” is an attainable state for anyone. That maturity is attained and expressed in mutuality. There is a community implied here, an invitation. And repetition, a future. Many centuries later this knowledge would be resurrected in texts by Goethe, Tocqueville, in the weak ties hypothesis, in the design of internet browsing.
If we accept that we are in the territory of joys and souls, that centuries if not millennia have been devoted to deciphering why mastery might move on a spiritual trajectory, it is worth looking at our confusions in more detail.
*
Right now in America, we use stupid words like “meaning” and “purpose” to avoid talking about our soul. To avoid talking about a wholesome internal life — intellectual, social, and moral. To avoid talking about the fact that people want to exist in ethical systems that they can trust. Ethical systems that trust them.
We don’t want to talk about what people truly decide on in the moments of choosing a life. We don’t want to admit to experiences where so much is at stake and where we have so few defenses. We don’t want the responsibility of irreversibility. We don’t want to publicly admit what really happens when you articulate who you want to be — and what happens when you find out who you can be. We don’t want to verbalize that when there is a difference between the two, processing that is a process.
We do retain some Aristotelian intuitions that the medievals were so into — we say “calling” sometimes, and “work-life balance” a lot. We tell people to lift weights as a way to improve their mood, to go touch grass. That their gut bacteria affect their thinking and so probiotics will help temper that existential terror…
These are our current feeble attempts at formulating that we wish we were on a course in a promising direction that is both spiritual (intellectual) and practical (material). The understanding that this course is impossible to get on alone, and that it is JOY that signals to us when we are on it, was somehow thrown out with all the other religion stuff, leaving us with no categories to grab onto, just these wordless sensations that we all feel.
And the inkling that in specific arrangements, certain people can build this kind of joy together.
Bildung.
That sometimes there is a conflict between the practical and the spiritual — that what you do with this discrepancy matters very much. That in fact everything in life depends on this.
And so it has become just hard to talk about what is taking place in the mutuality that leads to mastery — also known as: mentorship. The fact that mentorship is a form of world-building, where words create reality, where both the spiritual and the physical/material conditions are affected.
*
Three factors must be discussed first:
(1) Service:
The fact that what people seek in life is social utility. We don’t talk about this lest it evokes hierarchies, subjugation.
Yet the question that fidgets underneath all human ambition is timeless and elementary: Am I going to be useful?
And so — Accepted?
And so — Will I live?
(2) Freedom:
That people don’t like to be subjugated into the service of anything or anyone against their will — but they do desire commitments they could choose freely, so that they and the world can feel whole.
That after the tests and trials that one has undergone freely, one wants to reach higher levels of freedom. Not just through the autonomy that comes from expertise, utility, and social contribution, but also in the spiritual sense. Spiritual freedom is called salvation. There is a freedom in finding equilibrium, becoming one’s true self, living up to one’s potential, being able to take an opportunity. There is a freedom in knowing you’re doing the right thing.
Mastery is thus liberating in the technical but also in the spiritual sense. It can give you the tools you need to become and then live as yourself.
We all sense that liberation, redemption, and salvation are big, load-bearing concepts, and most people feel queasy throwing these words around when describing their own lives. But these words are there for describing real world lives, events, desires. You. Me.
And most people — if they were lucky and found help, then only when they are young — feel at least slightly misplaced in the world, and want passionately to find a better fit: peers, reassurance, relief. If most people didn’t feel like they had been born into at least the slightly wrong place, we wouldn’t have a universal Hero’s Journey at all.
But you don’t hear anyone mentioning redemption, lest it sounds too depressed, too religious. And yet, aren’t we all asking, at some point, at the beginning, or when going through great change: Is there a way out, up, away — toward ourselves?
What me do I have to abandon to become me?
(3) Love:
We most definitely don’t want to talk about love.
Even though we are deep in the realm of the inexplicable pushes and pulls between people which make little sense except emotionally. We don’t talk about this stuff lest it comes across as sexualized, or discriminatory, or — worse — both.
The thing is life is sexualized, it is discriminatory — full of connections and curations, fears, longing, and injustice. Making things non-zero-sum takes constant work, campaigning, and care, making this a great filter for finding the right collaborators, the right companions in life.
And so the question of love (choice + attachment) remains the eternal irritant between people, a challenge as old as the human family and the human intellect:
Is ours an encounter that is generative, or am I locked into a solitary fantasy where I just regurgitate my past and what I already know?
When we talked about redemption, we said people want peers, reassurance, relief. We can change up the order and say: all people want reassurance (service — “You are useful.”), relief (freedom — “You can be saved.”), and peers (love — “You are not alone.”).
When you look at these three things, you should immediately think: citizen. Images flare up of the ethical life. Of the member of a free society who can work, think, and associate freely. Of a knowledge of this that is passed down from generation to generation.
*
We shy away from talking about love also because we then would have to talk about luck — external circumstances — and talent — internal circumstances — . It would make it clear that life is rather unfair. Most people don’t meet the love of their lives in high school and spend a lifetime together. Most people never find the golden ticket to life-transforming mentorship and reach their fullest potential.
I have two things to say about this.
One: The fact that acquiring these treasures is possible but not guaranteed should make you more motivated to seek them, not less. Cynicism only makes finding them even less likely.
Two: Living with luck, talent, and stubborn attachments is not a recipe for happiness. Living in communion with others this way comes with very specific duties and difficulties. Closing an investment round, getting a book deal, or the birth of your baby is where all the work begins. Even winning a big prize is often just a prelude to a major effort.
These are nevertheless the good problems to have. All good relationships run on love — so it can be more than just a transaction, or competition, or extraction. So now information can be freely and mutually shared.
That sharing is JOY. At the beginning and during transitions people stand vulnerable. Joy exposes us and makes us worried about loss. Developmental psychologists insist that love is a prerequisite of all childhood learning: the attention, the positive reinforcement, is what locks in the new information, it is the confirmation that the learning has happened. It makes me wonder if what love does to us in all our important relationships is make us forever beginners.
*
Of course, if a math teacher started talking about how much she loves her pupils and wants to ensure they are prepared for service, and if a student of hers started talking about how much they want to be liberated or redeemed by that teacher, both would quickly find themselves in some therapist’s office, or worse.
And so these feelings vibrate in our relationships that are tasked with shared ideation and mutual betterment, unspoken.
The job of the Fool is to say things that others won’t. But it’s not just a matter of will — we often can’t talk very clearly about our more mysterious, one-off types of relationships, however important. Metaphors and comparisons are sometimes helpful.
In the case of mentors, people first bring up parental analogies. I think this cheapens it and removes the core problem of individual choice and interpersonal loyalty. Family is easy to talk about because we all understand the lack of control that comes with being related to arbitrary people and having to somehow deal with that. When it comes to our mentors and mentees, on the other hand, we have too much control and, subsequently, responsibility.
It is also not useful to compare these arrangements — which so often include more than two people anyway — to romantic couples. Romantic love is the original cliché, with the Lego bricks of our entire cultural history available to build from. If all lovers are similar, then mentors and mentees are always too original. How to generalize across a bunch of weirdos who are happy to cause mayhem in entirely new forms of relating just to pursue an idea or plan?
And so, both as mentor and mentee, I find myself in the wilderness. A Wild West of human relationships where anything can happen — no holds barred in some very real way. We’re in a territory of nothing but the human character in raw interaction — I’m not going to say “unguarded” because people of course devise all sorts of tactics to protect themselves, but given the lawlessness of the game, most of these strategies fail. The standard institutional structures and norms are not there to mediate, and so it is just character clashing with character. And all this happens during vitally important decisions in vitally important moments with vitally important people.
We are in the territory of theater, but the blood is real.
We know instinctively that this is ART, artistic collaboration, artistic creation. Just like in groups that create art, mentorships also throw us back into times before explicit social contracts, into a world of clans. Each clan in some sense makes its own law so that it can hold the big characters and the big stakes. The reason why great mentor relationships are so unique, so different one from the other, is because they were each created from scratch. And why the best mentors tend to have had great mentors themselves where they learned and apprenticed so they can arrive into these new relationships of their own with at least a little head-start.
The purgation in this kind of emergent self-organization is that at least at the beginning many mentorships will reflect earlier personal life dramas — the shadows of parents and children, of siblings and marriages — as participants work on figuring out just how they can build out for themselves a functioning information system that sparks joy. Bildung.
A relationship built this way is always a zero-to one, creative act, a one-off — terrifying and inimitable.
*
Many friendships are also forged in the “Wild West” of human connection. Outside of school or the workplace, religious or military settings, friends are free to negotiate whatever their bond means to them. The difference is that in mentorship, making crucial life decisions is the default. This is less common in friendships, unless you go to war together, perform open-heart surgery on children together, or climb Mount Everest tied to the same rope — all of which can of course happen. In the end, many mentorships turn naturally into friendships, often once the great decisions have already been made and the stakes have normalized.
Friendship might be a form of philosophy. Mentorship is always an art. Art as both form and content — material and spiritual.
Even at its most intense, joy is intangible, invisible, logos. In the next section, therefore, we will look at what happens when our ideas take shape in the real world, when risks are real and invoices have to be paid.
The physical manifestation of joy is pleasure, and I will argue that despite the many complications arising when real money, time, and bodies are at stake, co-creation is one of the great pleasures of human life, in fact our greatest —
Adventure
If mentorship is an artform, then these relationships must be a Gesamtkunstwerk, synthesizing so many different types of attachment, expression, aesthetics, and excellence. Because this kind of creation is so ready to hold together so many contradictions, it is also able to absorb many different types of characters and interests. When they feel like they’re on the right track together — when they feel free, accompanied, and utile — people who would have never otherwise associated will become super-productive soulmates.
One of my most formative memories of childhood is about the workshop. Throughout the 1980s my parents created and ran Hungary’s most popular TV show — this was in the era of the “one TV channel television”, and so basically everybody in the country with access to TV would watch that. My father produced and sometimes directed the episodes, and my mother played the title character. Every week, I remember the members of the senior crew arriving to our Budapest apartment overlooking the Danube and the Parliament’s spires. These men and women — writers, cameramen, editors, interns — sat with their notepads and cigarettes in our living room, and created the TV show which then millions of people would watch together. My childhood was far from idyllic but I know viscerally that what I saw in that living room week after week was happiness.
A big room with a view and hardwood flooring, a coffee table, a couple of worn sofas: maybe not how the medieval mason would imagine a workshop. But the location, the physicality almost didn’t matter — what mattered was the pleasure of togetherness. People arrived with less mastery, and left with more. People arrived with vague ideas, and left with concrete plans for rearranging reality. These changes arose from their characters colliding. Mentorship, challenge, mutual support.
The workings of the workshop have never stopped fascinating me. The fact that as few as two people can come together and become a productive community. That like some genetic code, like the spider its web, people spill out these containing structures around themselves that predate all the polite HR talk. That we all carry this DNA of spontaneous, chosen, from-scratch families in which the most ethereal intellectual developments can unfold and in which people can feel free.
The Fool, as usual, will look around in history, to see if previous times might have been better at concretizing how this can happen.
*
A few years ago when I read Hilary Mantel’s Wolf Hall I was struck by what she seems to have figured out about the workings of the “household”. (Somehow no one ever brings up this part of the book?!) My friend, the history professor Erica Robles-Anderson, always talks about the oikos — the household — as the core of the economy.
How Mantel’s Thomas Cromwell runs his household in the book reminded me in a fundamental way of how I run my startup Interintellect: after Penelope’s and the Durrells’, Cromwell’s might be literature’s OG “family firm”, comprised of his relations, allies, and a hand-picked squad of intelligent young men and women that he’s training the same way as at the beginning of the story, in his own youth, Cromwell himself apprenticed to the soon-to-be fallen cardinal Wolsey. If you noticed the combination of practical/political + spiritual here too, well done.
Century after century, societies change and improve, and yet these clan-like organizations persist. They seem to form automatically in human communities, and succeed at containing human events of life/death importance. These units lead to unthinkably good outcomes the participants would never have been able to reach alone: in art, business, science, or grassroots politics the right combination of people — duos, groups — can win big. (Consider the great praxis of famous mentors like Tyler Cowen, an artist who invented his own artform.)
The dark side of “clannishness” is that groups that make their own internal laws and are quite obscure to outsiders can also degenerate into awful examples of cults, fanaticism, abuse. We started with the three rules — service, freedom, and love — because the removal of just one of these will make the formation less healthy and less stable, if not altogether horrible.
This spectrum is indeed wide: individually negotiated creative partnerships can be the biggest, most amazing adventure in life, or something unpleasant, or even disastrous. The spectrum is so wide because of how high the stakes involved: when we enter these information systems, we bring with us the fundamental stressors of human existence. Who am I? What do I do with myself? What is a person for?
In the crucibles where these questions are decided, a lot of things can happen. People who want to be seen as “weirdos” (but aren’t) like to criticize “group think” and “decisions by committee”, as if n+1 people would always mean worse. This has not been my experience: finding just one good collaborator can make you and your decisions much more extreme, and when the direction is good, “more extreme” is good news.
A good community can make all the participants move much faster in the good direction. Unlike superficial friendships, the very raw and artistic friendship that is mentorship has practically no middle class: ye who enter here will either become very good, or leave. This is not something people can half-ass, since the whole process is about concrete, even binary decision-making about life and self.
How to be good? How to be better? — These are not questions where the answer can be “Maybe”.
*
I have recently attended a dinner in New York, and when I revealed that I was working on an essay about mentorship, a vivid conversation sprang up among my friends.
The first thing they asked me was to try and define the term. They felt they had been sold a bunch of different notions of “mentorship” — but there was a great difference between the many types.
As I kept asking, two things became obvious. One is the dilution of the term “mentor” in America (looks like we’re not only using “purpose” and “meaning” wrong).
Apparently, a “mentor” these days can be…
your former doctoral advisor with whom you build out a lifelong collegial relationship and who becomes the godmother to your first child
a colleague at a new workplace whom you’re meeting for the first time, showing you where the coffee machine and the toilets are on the first week
an intellectual elder you meet in the comment section under his article who becomes the primary blurb on your next novel’s dust jacket
a person assigned to you by a stranger in a business accelerator because you work in vaguely similar fields whom you’ll never see again
someone sitting next to you on a 90-minute flight whose words will stay with you as you navigate life forever… …
People to whom mentors were haphazardly assigned, or who accepted into their lives some mentor-wannabe promoting him or herself, now think mentorship doesn’t work, is just some kind of scam or urban legend.
People who found a transformative experience through someone else’s guidance or who were able to be there for an entrant through various life changes themselves think otherwise.
For some people, their “master” was their first boss. For some, their dad. For some, the one who got away… The one thing everybody agrees on — recall how we established mentorship as one of life’s important relationships — is that When You Know You Know.
That the category comes into existence when you respond to it emotionally and undergo some change. That masters, mastery, and choosing a life for oneself are of vital importance, and so you know when it’s happening by how important it is to you.
From his or her end, a good mentor also — consciously or instinctively — picks and guides mentees based on how important this whole thing is to the mentees. You can’t help people to whom their own selves and futures are not important enough. And if you are a mentor, you can tell how important a mentee’s self and future are to them by how important you are to them. (How much is this person betting on this?)
I warned you early on that we’re in an emotional, seemingly irrational, often selfish territory of self-creation. Self-creation — even when those ethereal values and heavenly joys are included — is a greedy venture. There is always a demand that is being expressed here, because we’re in lawless country where, as in a family or in a couple, there are no real rights. In some elemental way, the mentees have to show their teeth and fight, and not care what anybody thinks. To come and get it... Self-creation, for everyone, is always hard and always earned.
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I never consciously sought mentors until my work became vitally important to me.
In an unconscious way, maybe. The child psychology pioneer Nicholas Garmezy found that most children who grow up in dysfunctional families will go on to fall out of school, develop behavior disorders, and never fully integrate into society. But to his surprise he noticed that around 25% of these kids — likely due to sheer genetic luck — will develop strategies to avoid this fate. One of these strategies is, for example, mentally re-framing difficulties as challenges to learn from. Another is that the child will go and acquire mentors, external sources of security and certainty.
I definitely did this when I was a child: in absence of an extended family I could rely on (a household, a clan) I acquired for myself a whole arsenal of hopefully helpful adults from godparents to priests, from older schoolmates to my dad’s girlfriends, basically anyone who felt safer than the world and who could help me understand the world better.
When I was a young woman I was very pretty and very insecure, and so, to avoid giving myself “problems”, during the intellectually most agile and formative years of my life I had to mostly steer clear of older, powerful men who were not immediate family, which for a while greatly restricted my access to knowledge and instruction. In those “jeune fille en fleur” years I felt safest in the library, where I indulged in solo-mentoring, AKA reading every book I could get my hands on. After a while, I started building strong intellectual friendships with men, sometimes online or via correspondence, and learned that — as Alice Evans argues — friendship truly can be a truce in the battle of the sexes.
Until my late 20s, I never felt like I should build a career. I had my writing, which made me no money, and thanks to the other side of my personality which likes to meddle and is generally a busybody, I earned a living via all sorts of fun activities like lecturing at the university, writing articles, translating books, managing bands, building a women’s rights platform, shooting commercials, and so on. In my literary life I never wanted mentors: the great writers tend to be antisocial or insane, and in any case they can’t explain to you how to write; I knew even as a teenager that one learns how to write by reading, and that writing advice like “always sit next to a window” or “edit in the morning” are bullshit. The men who proactively tried to give me advice as a young poet I was wary of. The one true genius I met in those years thought I was a brat and that my poetry was terrible.
On the other hand, my busybody professional life exposed me to a lot of very interesting and intelligent people, often at the top of their fields. But because whatever job I was doing under their hands wasn’t vitally important to me, they too never became vitally important. There was nothing at stake for me, and so our transactions never became relationships.
A person’s desire to find help with getting better comes from having found the thing they want to get better at. It starts, I guess, when your adult identity starts. Or maybe it should be called an “intellectual puberty” that hits one in adulthood. For some people, of course, this happens at a very young age. For some people later, or never. I was almost 30 when I first grasped the stakes.
Since then I’ve had some quite cathartic experiences both as a mentee and, more recently, as a mentor. My first two mentors I lost when I left their field; our relationships, for various non-problematic reasons, never morphed into a friendship. I lost my only real writing (well, screenwriting) mentor due to the jealousy of a third party. In another life, that would have been an excellent collaboration.
My most recent “loss”, around five years ago, was a mentorship that never happened, I was just lobbying for it. It taught me something that’s probably obvious to everybody else which is that people are not who they say they are in their books. That joke is on me.
These days, the handful of people I view as my mentors vary in age and in character; with each we have built a specific kind of relationship or are in the middle of building one. As I get older, our exchanges become more mutually instructive, more equal. I would say most of them are today friends. (Not in the English sense, but as amicus/-a, someone who is loved.)
Mentorship is complicated but not for the reasons superficial observers would tell you. Sure, it is competitive to get into one. Sure, class and geography can create hurdles. Yes, the Me Too movement happened for a reason, because for a long time bad people got away with bad behavior within relationships of trust.
But these to me feel circumstantial, not inherent difficulties. I think there are inherent difficulties about mentor-mentee pairings and adjacent groups that can be better understood using metaphors such as clans or the theater — because they are problems that arise from within human nature, not arbitrary social situations.
And so in the next section I want to talk about things like talent, rejection, rivalry, and rebellion — the big human forces that are always present, even in the most carefully selected, most virtuous settings. They are simply the baggage people bring with themselves into every room they enter. And when in the room that they are entering they seek to improve themselves and confirm their identities, this baggage will not stay unpacked for long.
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Exploring contradictions is one of my favorite hobbies, and the matter of mentorship spoils us with examples.
Somehow popular psychology convinced the world that people like to give and receive the same way. I chuckle at this every time I read about “love languages”, fully conscious that for me — and I’m pretty sure this is quite common — giving and receiving love work completely differently!
In my case: the currency of my job is default enthusiasm. As a result, I express my love with genuine enthusiasm. (If you like a blasé girl, there’s nothing for you here, please move on.) However, as a downside of my job, I distrust the enthusiasm of other people, in fact I completely tune it out. The only way one can prove oneself to me is through perseverance. After a while — years? —, my distrustful brain calculates that any calculating enthusiasm must have worn out by now, and I start trusting the positivity shown to me as possibly genuine (but I keep in mind it can still be lost in an instant anytime, and so there is no reason to take it for granted or anything).
I’m mentioning this because this is a rather big delta, and it shows you how people — even when they seem relatively well-adjusted like I sometimes manage to do — don’t really need any external help to bring these giant contradictions to the table.
If you want to build such an important relationship as with a mentor or a mentee, it’s wise to start by examining the first, most obvious, contradiction at hand: that we all are very different people as mentors and as mentees.
As a mentee, for example, I tended to be like a philosophical five year old who asks mentors to explain not just why the sky is blue, but what it means. Most of my queries — except during exceptionally trying times — revolved around the Big Questions. About life, society, why people do what they do. It must have been very annoying. I never exactly asked “How can God allow such bad things to happen”, but almost.
As a mentor, influenced by my own past experiences of always just hearing about Rayleigh scattering and theodicy but never getting much practical help, I now support my mentees who sign up for my program The GrownUp Table in very mundane ways: money, introductions, links, referrals, etc. Detailed, concrete advice about life’s problems. I listen, and listen.
I know I have a lot of responsibility there, and so in the process of trying to be more self-honest and helpful, I happen upon all sorts of paradoxes in my own behavior. How hard it is to convince me to join other people’s communities — while I have been running my own for many years. How I get jealous and sad when I see how much practical support and cheerleading my male colleagues get — but I am not sure I would accept the same help so readily these days. Etc. Etc.
I am starting to think these idiosyncrasies — this being in the middle — are really just what middle age is like, this stage in life where you’re somehow playing both teams and neither. And so we look to friendship, love, shared obsessions and passions to help contain it all. People know deeply and instinctively that love-based relationships are personal breakthroughs that then lead to social, structural breakthroughs. It is human sympathies, always, that subvert the material conditions.
Being in the middle — in age and in career — has been very beneficial for my fuzzier relationships. Middle age is a great leveler. Everybody’s exhausted all the time, you can complain to each other, dad jokes are welcome… The baby photos only get more adorable with each passing year. I am all in to hear about new musicals and protein shakes, to celebrate someone’s eldest’s high school graduation, or real estate purchase, or the publishing of their new book, and I love investing in each other’s companies.
Whether it is explicit or implicit, communal or solo, mentoring or being mentored, it does feel good and natural to age into the middle, and see what love can build when you really care, and that it lasts.
Bildung.
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A great way to build anti-nihilism is by caring for your mentees. The great ROI of mentoring for the mentor is hope. Mentors and mentees are trading with each other, and what they are trading is stability for hope.
The fuzzy system that mentorship is can build the ad-hoc structures that contain the joy, innovation, and creativity responsible for this hopefulness so that the trade can be ongoing.
This trade, of course, creates peace and abundance.
A lot of these processes are deterministic, meaning once you have set up certain conditions — once you have made certain decisions or commitments — specific series of events will logically follow. (Unless you break out of them, change the conditions, etc.) Mentors tend to disagree just to what degree different phenomena are deterministic. Their opinion about this greatly nuances which parts of another person’s life and career they will want to get involved in, where they feel they can be the most useful or collaborative.
To illustrate a couple of different takes on determinism, I will use the example of the brilliantly written TV show, Mad Men, since the show is, first and foremost, about talent. (Also because I think it’s one of the best dramatic writing ever produced in history — Proust would have been writing things like this if he had been born in the 1960s.)
If you watch it carefully, you will notice that Mad Men is in equal parts materialistic (conditions) and idealistic (individual will). In the world of the TV show, some phenomena are subject mainly to conditions, while other phenomena depend on individual ability, choice, free will. In simpler terms, some events the characters can alter or fight freely, and some events alter and fight them. (The whole series should be titled “Talent and Love in America — A Philosophical and Sociological Investigation of Materialism and Idealism; 1961-1970”, but that would sell less well….)
In Mad Men, most love is shown as conditional, subject to circumstances. Most personal values are shown as held inherently by people — the values don’t change when circumstances change. The most important value in the show’s universe is talent. Talent is shown as the least affected by the outside world, by external change.
Consider some examples:
Don Draper’s marriage to his second wife Megan disintegrates when her situation changes — when she leaves her job, moves to California, discovers new aspects of her personality and ambition, Don falls out of love with her.
Don’s personal moral code persists wherever he happens to be, sometimes to unsavory or comical effects.
His talent — or the talent of his protégé Peggy - are also completely undisturbed by the frequent job moves and company M&As…
This surely is one worldview. In my personal experience, it’s just one of the many possible ways things can turn out. In real life, there is love that survives change. (In fact that might be the very definition of love!) It can be stubborn, something that just won’t die.
On the other hand, a lot of talent can be as sensitive to external conditions as a butterfly’s wings. How many gifted people you know who simply lost their mojo in a new situation that was just slightly different from their previous one? This is eerily common; there’s a reason why high performing people are so superstitious about random habits or objects — swimmers their slippers, Go players their mugs — and try to avoid change.
As a mentor, just like Don Draper and the great writers who created him, you too will have a specific worldview about what is internally vs externally deterministic.
(When leaving her mentor — as it later turns out: temporarily — Don’s protégé Peggy says to him: Don’t be a stranger.)
Examining your worldview is always useful. Where a mentor locates causality (circumstances vs will) determines what advice they give and which lever they try to pull. If you believe that people just have to move to the right city or get a Patagonia jacket or “drop the The” for their talents to flourish, your advice around talent will be materialistic. If you think people are born with a potential and that potential will bubble up regardless of where they go or whom they spend time with, you will need to be cognizant that you are likely an idealist. Both routes have upsides and downsides.
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Mentor-adjacent communities are a great place for softening dichotomies such as between materialists and idealists. In a well-run household, there can be a place for many different types of character.
We have discussed solitary mentorship (reading, fantasies), the primordial chaos of intense 1:1 relationships, and the importance of the clan-like — almost pre-modern — creative community.
Anyone who takes their work and mission seriously should seek out all three types of mentorship at least once in their lifetime, with special attention to programs — in my world these are Y Combinator, Emergent Ventures, Thiel Fellowships, the OSV Fellowship; all life-changing organizations — that can offer all three at once.
Where this is not possible, you may want to listen to Katherine Boyle, and build yourself a “mentors portfolio”, a list of people and their guidance that you find useful. And if, for whatever reason, you don’t end up finding the exact guidance that you need, you might still one day become a master to others yourself, the same way some of the best parents and teachers strive to give younger people what they themselves wish they had had.
Mentors who are interested in talent at scale will want to engineer conditions that make this feasible. If you browse X and encounter long threads by billionaires trying to figure out whether four or five geniuses per office is the right number, you can tell just how mysterious these chemistries are, even at the highest level.
The most successful mass-mentoring programs that I have seen tackle this problem by (1) understanding that “at-scale” means having to build a community so the founding mentors are not in the center of every relationship at all times, and (2) creating a balance of three forms of interaction that promises to be sustainable and to boost each other in the long run.
These three are:
(1) Support
Mentoring programs that successfully establish the right conditions for talent to be discovered and to grow always offer some form of one-sided support. This means that someone senior in the organization — the leader, the midlevel, or senior members — can give advice, help put out fires, share useful resources, or just … sometimes … listen.
Without this altruistic support, mentorship programs will come to resemble meat markets, where especially the younger mentees will feel like they are being watched indifferently for sink-or-swim signals. Without support, the communities will also risk becoming just workaholic sweatshops focused on competition and output.
(2) Competition
A strong community around any mentorship program will be ripe with friendly competition. You can’t really “raise people’s aspirations” without people starting to compare themselves with each other, and taking cues, taking action. Good mentorship is fundamentally meritocratic, and thus also capitalist. In competition with one another, mentees will grow faster and bolder, and in the end achieve more. Since they can count on support, it will not feel like a Battle Royale, it will not become zero-sum.
Competition within a safe space is how small labs and scenes become so successful, and mentorship programs can imitate that structure at a wider scale. Without competition, mentees who are expected to fight and improve would grow complacent. It is never a bad idea to keep people that you want to achieve a lot on their toes!
(3) Collaboration
Something we rarely discuss outside the oeuvre of notable serial co-writers like Paul Erdős or Cass Sunstein is that mentees want to work with mentors — recall the medieval workshop — such collaborations being the ultimate proof that they are graduating from the program. As it was for the master blacksmith in his 12th century workshop, so it is today in intellectual and artistic sceniuses.
Without collaboration, support will feel condescending, and competition pointless and heartless. It is tough to do at scale, but it’s important for members to feel that there is at least a chance for eventual co-creation. This really is the ultimate form of invitation and, luckily, for most mentees a simple gesture will do.
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Be prepared that even a fully balanced triad of these can’t always hold back the sneaky beasts lurking in the muddy waters between equality and meritocracy. In fact, throwing a lot of crazy ambitious high achievers into one arena before they have become fully confident or autonomous is a great way to rouse them.
But the equality vs meritocracy conundrum isn’t the only issue that mentor-adjacent communities will deal with. There is also the hard fact of life which is that however humanistic and harmonious a talent incubator and support program might be, the individuals within it will have to exhibit some very inhumane traits in order to achieve great things.
This isn’t something Instagram influencers and fridge magnets will tell you about. But we all know, deep down, that the activities required for significant, outlier lifetime achievement can be pretty unhealthy. You already know that people ruin their backs and eyes reading and coding. How they forget to file their taxes while finishing their books. How they stay locked up in their studies to the dismay of their families, how they stay up all night and look like zombies the next day. Plants die, dogs go unfed, and cats pee into bathtubs in the homes of the exceptional. Analysts’ couches are teeming with people who grew up with high-achieving parents. People get angry, depressed, and hyper when working super hard. People feel lonely, go bankrupt, and are left by girlfriends when doing their best work. Before successful people get all dolled up for award shows, there are all the decades spent with a much less elegant appearance. (I am typing this at 4 am with ice-cold fingers, wrapped into a stretched out cardigan.)
There really are but a few types of relationships that can make this process less jarring — there are people who can pull us out into the light, at least to give us brief breaks. Some, sharing joy through collaboration, might even join us in our rabbit holes of achievement. Some, through sharing wisdom and showing us a more mature version of ourselves, might help make our workshops feel sacred and our efforts more worthwhile. A lot of greatness is born in dark places, but it doesn’t have to live there.
When we are that mess, it is our lovers and relations, our friends and our mentors — our loved ones — who will see us. The beginnings are expected to be hard. These intermezzos always come as a surprise.
You will hope that determinism is on your side. And you get it on your side by choosing the right people.
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Due to the fuzziness of their category, and because they sit somewhere between the world of friends/family and output/work, mentors can feel like guides between the public and the private realms. Many of them see themselves as gatekeepers. This is one of those gates.
If you are currently looking for a mentor, you will want to choose someone who is equally comfortable with your public self and private self. People who love the public you but can’t accept the “backstage” you in moments when you’re less ready, less sure, less fun, might be the perfect promoters but not necessarily mentors. People who thrive on your weakest private moments where they can feel useful but are envious, dismissive, or overly critical of your public work may be adequate coaches, but their approach seems less than holistic and you might want to keep looking.
As a male mentee, you will want to be careful with mentor candidates who praise you onstage but who chastise you for having weaker moments or reaching out for help. Sure, anyone might perform public admiration if it makes them look more in the know. Not good enough.
As a female mentee, you will want to be careful with potential male mentors who want information from you, or your attention, or to be entertained by you in private, but whose public appropriation of you — acknowledgement, collaboration — doesn’t match their backstage zeal. These are things you shouldn’t have to ask for… My general rule is: “If you think I’m so smart that you want my ideas, then this is something more people should know about.” As a woman, unless they put you on a stage — a mentor is an invitation — they might not be such mentors to you after all. Remember that everything around a woman is set up to infantilize you and make you think you have to lower your expectations. Don’t.
In general, as a woman or otherwise underprivileged entrant, assume that you have already paid an enormous price to even get anywhere near a mentor, and just stop paying the penalty even if others act like you need to pay it forever. As a man, surrounding yourself with people who make you feel like you can’t fail (and so: improve) is a surefire way to be pushed off the course of your own talent and onto some normie road leading nowhere. The gravity of conformity is very strong for men; you will need to find a match who can help you become positively more extreme. Remember that everything around a man is set up to make you become disingenuous — as if the archetypal American couple were “Lying Man and Female Child”! — to pretend to be always strong, to stay with the pack. Don’t.
As a mentor myself, I try to speak openly about both my public and my private selves and the challenges thereof, so my mentees can feel that both are OK to have, and that it is OK if these two lifestyles are quite different.
The balance requires some ongoing effort. In the case of longterm mentorship, people’s situations can also change: mentors and mentees become more or less busy, more or less public, more or less wealthy, more or less interested in the minutiae of psychology as time goes by. I don’t think anybody can ever behave perfectly. But I know that love and care can go far in providing a buffer amid these many fluctuations.
In mentorship, the most brutal part of the public/private duality is rejection. Our mentors might not know as much about us as our friends, lovers, or family do, but it is still a uniquely information-dense relationship. And so being or even just feeling rejected by a mentor, who has such access to the thinking, the data, and the backstage, can feel disproportionately like some kind of apocalypse.
If rejection must happen, remember that mentors are tasked with giving feedback and guidance, and so I think it must come with some explanation that the mentee can then use constructively.
Perhaps you can tell that I am trying to ease you into the next section where we will discuss the harder aspects of mentorship, the stuff that — at least to me — are bewilderingly difficult.
I know this is America, and you’re not supposed to talk about how painful life is, and how much even good things can hurt — unless you’re Taylor Swift, I guess... Or dear Aella.
But I am not American.
Pain
It might indeed be the Eastern European in me talking, but I consider difficulty, even suffering, a natural part of life; I can’t imagine important projects, important places and, especially, important relationships, not to come with complications, not to create some pressure in my life that force me to grow and be better.
Mentorship is, in fact, the important relationship in life that we pursue for this very purpose: we want it to pressure us in some way — we hope not too painfully — so we can improve, break through, develop into masters ourselves.
We’ve already seen that this is a fuzzy, artistic type of relationship where a part of the energy is always spent on trying to ground the relationship itself into something sustainable. We’ve established that the stakes explored within mentorship are uniquely high: money, success, who we get to become and see ourselves as. This is just as true in duos as it is in groups, just as true for mentors as mentees. If your work and your life are important to you — and they are — then your mentors will be important to you.
And so mentorship already seems both quite unstable and insanely weighty when we consider that…
learning is default painful and beginnings are often embarrassing (nobody looks very glam backstage)
we seek out mentors who can pressure us to become better (and coexist with us when we have)
if strong emotions — hope, love, respect — weren’t involved, the whole relationship wouldn’t exist in the first place
due to the joys felt in shared collaboration, there is a fear of loss that informs behavior
due to a lot of information being shared, rejection looms extra scary
how creative groups — even two-member ones — amplify talent and personality, push them to extremes
how even in harmonious arrangements, there lurk negative or destructive behaviors due to how competitive it all is and how hard the work is
we fight for and earn mentorship during often long periods of time, and so these people in our lives are not so replaceable
…. and … long exhale.
Looking at my own list here, and thinking about the beloved mentors in my life today, the fact that any of these attachments were really stubborn enough to survive for as long as they have feels like winning some kind of uber-lottery. It makes me feel very blessed.
It also speaks to the power of cultivation — once again: connection + curation. Voltaire tending to his garden. That the threats are always there, so great, so constant, but one can always focus on just one little tree at a time.
Can it be that mastering the mastery is in itself an act of virtue where we acquire both practical and spiritual knowledge?
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When prices are high, losses hurt like crazy. Especially in relationships that unfold in time, on the serpentine roads of real life, just what “winning” means is always changeable and elusive. In some sense, nobody “wins” in the long enough run. In the long enough run, you die.
Yet the only way not to involve your soul in this process — during which process you want to build real relationships and real mastery — is to not get involved at all. Bildung. So a lot is asked for here, and there is no clear or definitive victory in sight.
Tough.
The Fool sees the small feelings, the incertitude, the tears. Vulnerability. The down moments, the helplessness. That like all artistic collaborations, or the interpersonal events of families or faith, these associations are psychologically exposing.
Self-help literature addresses this exposure from the POV of personal agency: what you should do, how you should be more productive. But these psychological events are interactive, and they’re better understood as events within an information system where the information being exchanged is vital.
Good mentor-mentee duos or groups are both intimate and expansive enough so that the relationships can act as a kind of insurance. A mentorship that takes into account the pains of life will ensure that during hard times the mentee has continued access to good counsel and personal encouragement — and that during the less colorful periods of the mentor’s career, when they are not successful or popular enough (or anymore), they will still have access to the mentee’s energy, hope, information, and love. As we have seen before: these are not trivial matters. These are the moments that can make or break a career.
In those hushed corners, on the days we are not proud of, when we have to step up and do the hard thing, people can feel especially defenseless. And yet it is there that the really important connections are sealed and the truly life-changing decisions are made. In those moments we really are primal, primates — just parents and children, each all, held together by care. I like to joke that no one is truly an adult at the dentist’s, or with their pants down or skirt up at the doctor’s. Will I live? Will it hurt? — these are questions that can only be asked from a position of humility, whoever you otherwise are.
It is in the small moments that we understand that expertise is existential and learning is survival.
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We started our investigation into mentorship by contrasting mentors with muses. This was not coincidental or just alliterative.
While my friend might be writing a book about the Muses in the Greek sense, I am far more interested in the people who swoop in from out of the blue, or whom we go and seek out, and who then have a great effect on our thinking and motivations. Unlike with mentors, this act of “being touched” seems one-sided and less an expression of personal taste or choice. Human muses don’t seem to want to build any kind of relationship with their happy victims, they might not even notice anything.
Some people might look like mentors but are in fact muses. And to some people who think we are mentors, we are in fact muses, too.
When this is the case, the importance and the impact are there, but the a mentee (a musee?) won’t feel like they’re securely part of an information system, or that there is some kind of insurance, or that they have been invited, granted entry, and now it is a reliable relationship. (Curation yes — connection uncertain.)
Before, during, and since the formation of Interintellect, the cultural conversation platform that I run, I have come into contact with some of the most exciting minds active today, from teenagers to octogenarians, in America and abroad, and with some of them mentorship and apprenticeship — collaboration and friendship — are natural questions that will arise.
However fuzzy their category might be, you can usually tell a mentor by how they are an invitation — an intervention. On the other hand, muses visit by invocation: you need something specific from them, and you might get it. It is a one-sided illumination — in practice, it is when it’s always one person asking, one person calling, one person travelling, one person needing, one person trying, one person growing. (In my case, if it is always I who invite somebody in, I know.) While mentorship is a moral technology, muses are amoral, unaware of ethics. They don’t want to be your role models or to improve on your identity. They don’t update their treatment of you based on your progress: a muse will suggest the same good idea to a 19 year old student and a 79 year old Nobel laureate, while a mentor grows his or her opinion of you as you grow and adjusts their advice. And so with muses there can be serving, even saving maybe, but no loving. It is not a community. Muses glimpse our hunger but not our vulnerability. Muses remain strangers.
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Apart from vulnerability — psychological exposure — as an internal condition unavoidable in important relationships where major personal development and decisions are taking place, there is also an external condition that good mentorship can contain. Crisis.
Since we don’t have many workable, established concepts for the extra-institutional world of mentorship today, this type of relationship always creates its own order, leading to the existence of longterm duos and groups resembling creative collaborators. Because its order is self-invented and individually negotiated, some of these relationships will end up being in fact much stronger than what normie collegiality or weak ties would provide. And so in times of crisis, often these are the only people in one’s life who can offer some sanity, reassurance. Insurance.
As a mentor, you will want to be especially careful to notice crises. Crises are decisive moments, that’s when people either transform into something stronger and better, or they will drop out and disappear. As a mentor, you should NEVER be indifferent about this — both because caring about mentees is your individual contribution to anti-nihilism, and because of the great social utility of keeping talent at work. Indifference is never a neutral, passive standpoint of “waiting it out” but the very opposite of involvement: where involvement actively tilts the mentee away from the chaos and back into the clan, indifference pushes her outside, signals that the connection has not happened, and that the best she can hope for is, if she somehow survives alone, a muse. (“Muddle through and then write about it.”)
People famously think they would notice if someone was drowning. They imagine themselves sitting on the beach and hearing the loud cries, then heroically running with the others toward the waving drowner Baywatch-style, and dragging him out of the water. Of course, those with any lifeguard training know this is not at all how people drown — in fact in moments determining life/death people go strangely quiet and motionless, both because of the shock and because all energy is being spent on not dying. The same happens with people in a major crisis. While mentees will always either complain or flex to mentors — there is so much chatter — the real problems are eerily quiet. Having some way of keeping track of people’s life events, behavior changes, and subtle signals (is a mentee suddenly asking for help about a different thing?) will go a long way.
Mentors are not responsible for the life decisions of mentees, of course. If a mentee decides to quit and go AWOL, they are free to do so. But mentors and mentees, in a dialectical sense, are fully and at all times responsible for the relationship they have built together. And if a life crisis on either side would mean the breakdown of this relationship, then that is a time to show care for sure.
*
In my adult life, I’ve had two major life crises so far. One happened in January 2015, when a violent event shook my life and forced me to start rebuilding it from basically zero. The initial dark night of the soul lasted about 20 months, and then it took me around six more years to get on the right track with my life. These things take time.
The other crisis was quite recent and lasted from March 2024 until about May 2025, during which I went through (1) major and sudden bereavement, (2) cross-continental relocation and related immigration, administration, and financial processes, and (3) had to solve a critical upheaval at my company that I had zero training for. All the while (4) I couldn’t write which made me feel like a shameful slacker who was being pushed farther and farther away from intellectual companionship and losing everybody’s respect.
The 2015 crisis cycle I did with no functioning mentorship in sight (although I did get a lot of help by muse-like visitors — drive-by support, ideas, pointers). One of the reasons why I think that one lasted so long… On the other hand, during this recent one I had various systems around me technically able to support me. It was still unthinkably difficult.
Some conditions no mentorship — whether pairing or clan — can fix because they’re a part of its very structure. And so if you’re in a crisis already, the psychological exposure can be yet another problem to deal with. In my case, for example, moving to the USA in the middle of my annus horribilis upset the status quo of my support systems and sent many of my relationships of vital importance through fundamental changes themselves. “Not living in the USA” turned out to have been one of my pillars in these important, from-scratch relationships, it was part of my role in the clan. Until then to some degree I was a kind of fantasy, living in other people’s heads, and much more under their imaginative control — a parasocial creature without a Social Security number. Being finally in town now with my post code and CVS card was a baseline change in the determinism. (And so for a while I just didn’t know where to go! If both being and not being here come with so much loss.) Renegotiating vitally important relationships while going through hard times was hard, and it’s in some sense an ongoing process.
In a crisis, the love that is the basis of all good mentorship can also complicate the external and internal conditions, and mentorship once again can’t fix a condition that is itself. During my year of mourning, for example, I had to also process the unbearable notion that the next one to go would now be my most important mentor, and that if things go well and we both live long lives, I would still have to live out decades of my life with him gone — and then what will become of me, what will I do... This added a secondary layer to my already great grief, a nightmarish memento mori that is latently there in every key relationship and that sometimes comes and headbutts you in the face.
And so the crisis felt like some kind of torture. I can’t remember any other time in my life when I felt such a crushing mental anguish; even my body hurt, my internal organs. For a while I was absolutely sure that I had failed as a person, that I had lost everything and everyone, or would soon do. That I had ruined everything, that everything was a lie — what I thought was security or certainty. And it went on for months and months. There were moments when I felt I would lose it, honestly, just give up, drop out. Run away.
And then I didn’t. In fact I had to go and somehow completely rethink everything to be able to go on with my life. And I am glad I did.
I was left with some very surprising lessons like … love wins. That whoever and whatever is strong in one’s life, survives.
I also learned that having previously reoriented my life toward what truly matters to me had made me selfish in a way I don’t think I ever was before: I seem to now have the ability to hold on to things and people that are important to me not really caring how it looks, or whether it is “dignified” or cool. A lesson in connection + curation indeed. What me I had to abandon to be me.
And so maybe all of this was in fact a lesson in selflessness. Today I wonder if it hurt so much because I had to shed the old skin, to kill my ego. Let go of all the lies that I told myself. And whether it could finally happen at all because some security and certainty, however flawed, was there to hold me, to hold it all. That I was not really alone — and so I could crawl through that Purgatory and make it out.
… And then the Sun comes up, and one takes a deep breath, and goes back to the original question.
*
How to be good?
At what we do. As people. To each other.
How to be better?
In a mentor relationship, two people stand facing each other and try to do the right thing.
One person asks:
— Am I helping you right?
And the other person asks:
— Am I learning this right? Am I going to be alright?
We do all of this because we want to be better. Better humans. Better at being human.
The desperation with which we ask each other is what’s most mysterious and most hopeful to me about all this.
Our questions are already the answer in some way.
And the very fact that these questions are asked is proof that mentorship belongs in the realm of ethics. It is mutual Bildung. There is so much building going on: of the relationship, of a chest of drawers, a life skill, a soul. (“Building the builders!” — as Gena Gorlin would say.)
Since mentorship is an explicitly ethical relationship, in it selfishness and selflessness will clash — both between the various characters and inside people, internally.
The Kierkegaardian romantic in each of us will always strive to win this and to feel special, and will welcome any amplification of extremity that creative clanishness can offer.
All the while, the Hegelian paterfamilias in us wants clean systems and to feel like these unique interactions contribute to society at large in some substantive way. Those of us with an avid interest in how these fuzzy relationships, where stability and hope are in exchange, are built will hope they will indeed be able to contain all the egoism and vulnerability of the participants — our social successes and our private pains.
*
“- messze málló jósvonások nagy memento “M”-je vásog - minden alatt e nagy “M” láttalan és sejttelen - mérő szemeink elől a méretlenbe szétfolyó, -” — Mihály Babits
*
We talked about the psychological exposure and the life crises that complicate the deterministic processes even in a well-functioning mentorship relationship. We have understood that we’re in the kingdom of ethics where people go to become better. We intuit that there are two dimensions here, one public and one private. Our hope is that through these individually negotiated, complex and beautiful relationships we will acquire practical and spiritual mastery.
Given its internal and external risks, a relationship as important and as fuzzy as mentorship cannot be discussed without discussing also the world that surrounds it. There is a third condition that mentorship often can’t control as it is part of its own texture: Fame.
There is a joke that goes: “London has never improved anyone.”
I heard this when I was living in London. I tended to agree.
I think fame is like this too. Whoever you were when you became famous, whatever you then had in you, that is going to be you. You will keep that or lose that during your fame. Fame is not going to add anything to your life in an ethical sense.
Of course, most people do other things in life beyond being famous, and those other things nourish their lives to save it from stasis. But fame itself is a very tricky thing because famous people grow a secondary persona, a second life. Being in any kind of relationship with a famous person is like being in a relationship with at least two people at the same time (two of whom, being aspects of the same person, will be of course much closer to each other than you can ever get to either of them). Famous people, in this sense, always cheat on you with themselves. (If they’re also addicted, then they will also love drink, drugs, their work, etc., more than you.)
One reason why mentorship is so popular and effective in tech might be that tech people don’t necessarily seek wider fame even when they get very rich and successful.
This is important for understanding several things:
Paul Graham is VERY right when he urges you to keep your identity small. Fame must be instrumental and not its own goal: you should obtain as much fame and no more as is needed for you to do your job to your best ability.
If your life’s big emotional problem is approval-seeking, fame will be like heroin for you. It’s the ultimate form of seeking approval from everyone, forever.
Fame is a kind of fake joy but with a real sense of loss. As a result, decision making by famous people is always distorted by wanting to continue to be famous — or at least to continue to receive the dividends of fame. This can make innovation, the forming of new connections, the receiving of real feedback, and healthy life changes hard. In general, it’s a bad tradeoff because you pay and pay for it but then fame — in itself — can’t make you happy even if you manage to keep it. And it certainly won’t lead to more sharing which is a prerequisite to real joy. In many ways, fame is the ultimate social “diminishing returns”.
There is a reason why famous people — in entertainment, etc. — mentor each other so rarely. I mentioned that the secondary persona of fame is like a third party in any relationship, interrupting the mutual information that is love. When both parties are famous, then you basically are four people in that relationship, at least, with the fame projection personas controlled by a public outside the relationship whom like a Tamagotchi you have to constantly feed. This is an agonizing way to be poly.
If your mentee/mentor is famous, and you are an audience to their public work, you will have to consciously deal with this fact and manage your reactions to whatever they are doing in public, and with whom. Since they will be touchy about their public work, this will rarely be something you can honestly discuss with them, further driving a wedge between your realities.
The best use of fame is as a pipeline: to get you in contact with new people, deals, places. But even in the most benevolent scenarios, when people find a way to live with their own projections and a fear of loss is not so debilitating, fame is always smoke and mirrors. The people inside and around it will get confused, bump into things, and get hurt every once in a while.
More dangerous because more immediately desirable than wealth, fame is also a kind of dark fog for those way outside the perimeters of the relationship. Mentorship has to find a way to deal with this surrounding world.
In my internal dreamworld — where it’s always a spring day and the light is soft, and there are books and flowers and embroidered cushions, and outside the window the tram’s bell tinkles on the rainy cobblestones ……. and the smell of hot chocolate from the baker’s …….. — everything is always great and people are kind and peaceful. In my complicated, important relationships, this purity is not so easy to maintain.
And so there are, beyond the many internal conflicts, also these external threats to high-stakes, hard to define relationships. Jealousy and incomprehension, cancellations and doubts, politics, the impatience of investors. When you become a mentor, when you live your life entangled in these baseline-forming friendships, at times you might feel like you have crossed into enemy lines.
It helps to remember that none of us is innocent. Most likely the situation you are in is also the result of having wanted things you saw other people around you want; your choices were also affected by those of your rivals.
The good news is, outside one’s dreamworld, even in enemy territory, choices can be mutual and so can create some stability, a foundation. Loyalty under threat: might just be the definition of community.
As a mentor, I try to be conscious of how my potential mentees see my public self, whether I think it will cause problems. I am wary of people who want me on board because they want to become famous. That is definitely not something I want to mentor people toward — I don’t think anybody should, or even could.
(The Fool knows fame is just a costume; it is not an archetype, not a character, not real.)
I’m also conscious that as a mentor I am an invitation — both challenger and leveler. Once a mentee has successfully convinced me to care about them, I am supposed to interact and participate in the creation of the relationship, in the upkeep of my information system with them. This is a delicate thing — I still need to push them, keep them on their toes so they won’t slacken their ambition, and to represent some kind of certainty, continuity in their lives. Unlike muses, mentors might differ greatly in shapes and sizes, but they are always interactive. There is a reason I call my own organization Inter—… . Otherwise my mentees would feel like they have to always chase me, that they have to always wonder, always ask, always pay to see me, always invite themselves — seeing also my public persona quite one-sidedly, they would just feel constantly uncertain and eventually unworthy. While I’m more than happy to be a tantalizing drive-by muse to some, in general I want to participate in the ethics and the joy of collaboration when possible, and to build equality.
The structure of mentorship is complex and its goals noble. And while the world may try to restrict or derail our movements, people are able to unblock each other in an outsize way and to keep each other on track. When I want something very much, I ask myself: what would be the discipline to get me there, the routine? This may sound like a tame question that only concerns the surfaces of life, but with a true Aristotelian twist, it can in fact take us deeper, to some of the core contradictions that inhibit us.
And so I think we are now ready to go to the sources of all conditions — money, access, contracts, and bodies. For that, we will need —
Rigor
Engineered scarcity is a great way to signal importance — and to notice it. Keeping something scarce often requires self-control. Noticing it requires intelligence. Self-control and intelligence are a good pairing.
Great mentors won’t impose themselves on potential mentees. It is the potential mentees who have to convince the mentors to grant them an invitation (that we call some scholarships “grants” should be a hint), and to build with them a new and in its own way stable relationship.
If you are looking for a mentor, you can right away cross out anyone from your list who looks like they want you too much. That person likely has no idea how intense the work ahead will be, or they will expect you to do all the work yourself. In Jewish tradition, when someone wants to convert the Rabbi has to turn them away three times. He has to tire out those who don’t really want it, who don’t take it seriously enough. Since the applicant has to invest so much time, energy, and resources into the attempt, they too get a chance to double-check whether this is important enough to them. (And convincing gatekeepers is of course nothing compared to how hard the actual thing you want to do will be!)
Mentors with a passive personality will be able to handle this initial “courtship” phase well: they just have to sit and wait, and see who will be brave and proactive enough to land them and get “the invite”. For them, the reciprocity-based later stages might be more challenging.
Any mentor really can only choose from applicants who apply, who try — the most active they can get at recruitment is encouraging people to apply, to try. Choosing or rejecting mentees is a crucial choice, and often there are no backsies. I too have a couple of people in my life for whom I think I’m a missed opportunity: it would have been amazing to be invited / taken seriously / collaborating when the time was right, but it might not be so easy anymore.
From the mentee’s perspective, getting involved with a mentor — in their instruction, life, and circles — is both formative and very costly: in time, in money, in other opportunities. We have seen before that it is a type of “chosen stress” that we expect to push us to become better. It is also a form of “chosen sacrifice” like any important relationship. You commit to a few people and that is all the time or brain-space you have in life.
Because you have to choose your mentors so wisely (it is what determines which determinism will follow!) and place indeed such a huge bet, I am not buying the Robert Greene style popular adage that all mentorships “must break down” at some point. I am much more of the dialectical school — I think good relationships just become something else if enough conditions change, something that is equally good if not better.
As a counterargument, I should go back to the recent dinner I attended in New York City where the discussion about mentors ensued. Talking about breakups, I — always ensuring conversations remain in the highest echelons of arts and culture — brought up Gandalf and Yoda, and how they stayed closed to their mentees, to which another attendee countered: “Yes, but Gandalf and Yoda were both fighting giant existential threats! They needed everyone!” That’s true. Since that evening, I’ve been musing just what external existential threats or illusion thereof can strengthen mentorship pairs and groups today. What does it mean to “need everyone” to today’s mentors?
The thing is I can see how internal conditions can also enable these relationships to stay together, the same way as not every teenager breaks with his parents. Some parents are able to realize when their child has grown up, and reform their relationship into a kind of adult friendship. But if I consider how my own loyalties were sealed by personal crises and through mutual investment, I realize there may be a kind of general condition that is key here that is neither fully external, nor fully internal, the same way as mastery itself is never just material or just spiritual.
“Success is succession.” — as my friend Erica says. At the end of the day, what mentors, especially when much older than their mentees, work on is replacement. And not because mentees might break with them at some point, but because sometime in the future the mentors will die, and they will want to know they have left the world in good hands, that they have made a mark on it.
*
We have explored a variety of dichotomies that structure our understanding of what mentorship is, and the many ways in which this important type of relationship, however fuzzy and always negotiated one-off, can shape the course of a life and give it a kind of dynamic ongoing order. We have talked about mentors vs mentees, communities vs individuals, good times vs bad times — short-term mentorship vs long-term friendship, practical vs spiritual formation.
In this next section we will explore another interesting pair of contradictions, something I find a lot of fun. The Fool here feels very much at home: we’re back in archetypal territory.
And no, we won’t drag out the whole chessboard to illustrate our point, but two figures must be discussed right away, and why they matter when we talk about guardianship and guidance:
The King and the Priest.
First of all, this simple pairing shows just how much mentorship is a form of public service. Mentors — from bosses to professors, from incubator leaders to older relatives — tend to have far more mentees in their lives than how many mentors the mentees will have. (Outside close collaborations or friendships, the way mentees in the end can “pay back” their mentors is really only by paying it forward, and starting to mentor new entrants of their own.)
Leaning into one’s archetype has a huge practical value for a mentor. It’s useful for structuring interactions, managing expectations — it simplifies things. But even great mentors often have no idea whether they are Kings or Priests. People simply have a blindspot about this: it is hard to intuit one’s own archetype. You could say that all job titles, horoscopes, and personality tests are seeking to fill in this gap. This is about — as my friend and Interintellect co-conspirator Violeta Kristof would say — “What would Zosima whisper to you?” What is something that everybody who knows you knows about you, but is not readily visible to you?
Before I would explain to you this dichotomy, we need to talk a little bit about permission.
In business literature women, minorities, young entrants — in fact any entrant — are encouraged to “not ask for permission”. JUST DO IT. I think this is total nonsense. Of course, you need permission to do anything in society! Have you ever tried to walk out of a store with something without paying? Most things in life people just can’t do without permission, either legally or psychologically.
I’m not just talking about the obvious examples of contracts, permits, certificates, consent, and lease agreements — although even your most hipster crypto wallet will want to verify you. I’m talking about the fact that it is a psychological trait of human beings to not be able to do much in life unless someone else has granted them permission.
Permission-giving is a very, very important role in society we assign or usurp in a variety of ways. From like buttons to “sanity checks” with friends, from a smiley nod to finally being invited to that offsite, people give each other’s desires permission in a gazillion ways, all the time. In fact some people’s main job in life is to give permission! (Emily Oster — hello? Donald Trump…) Compare your before/after stress levels the next time you want to expense something to your accountant via your LLC, show up uninvited to a talk, or eat sushi while pregnant, and what you needed to be told to feel you can.
Sure, the ability to give your own self permission can be a superpower. But the core of human ambition is always social, you want to do something with / to / against other people. And so permission — in professional settings too — is a kind of guarantee that if you do this or that, people will still want to be around you after. That they’ll want to be friends, that they’ll want your ideas, that they’ll want to work with you.
We’ve looked at how in mentorship, there is always a question, mutually asked. When we consider just how thoroughly mentors are tasked with permission-giving (they are an invitation) we understand that in that mutual question, there is always a “Please.”
Please let me in / let me play / … … — The Infinite Game is an agreement. It’s somebody, at some point, saying “yes”. You can. You can stay. You can try. Please don’t let me down.
Of course — and thank God — mentors can’t do even the best mentee’s job for them. But they can give the mentees permission to do it themselves. And while doing so, mentors always wrestle with their doubt: Would this person do the thing even if I hadn’t given them permission?
Whether a mentor is a King or a Priest will determine what kind of permission they can give, and what kind of permission people will demand from them. This dichotomy will also show you why the word “gatekeeper” is not always so useful in understanding these processes.
(1) Kings
Mentors who are Kings make zero-to-one decisions over the existence of projects: they give fundamental resources — investment, job commissions, degrees, film or book deals, an SNL contract — that will enable a thing that otherwise would not exist to exist.
As in our medieval towns, where Kings gave title, land, and various liberties writ down in decrees, most “King mentors” these days throw around money on types of projects and people they want to see more of in the world.
It is a common misconception that a King mentor will then also be somehow involved in one’s project. A famous conundrum in Silicon Valley and environs is when some famous investor wires a founder — to the founder: a lot of — money, but then never replies to any email ever again. (This happens shockingly often.)
Unless you make friends, which is usually completely independent from the money or resources previously given, there is little opportunity to hang out with Kings. And that is probably fine: their time really is best spent splashing around value where they see fit, and then move on to someone else in need of permission.
While their interaction can be as light, Kings are not like muses: they are mentors. Kings do want to use what you make, they do want a stake, you are in some ways their own ethical self-expression (“I made this thing/person happen.”); they do provide stability (mostly money, but also sometimes advice, contacts) in exchange for a hope in a better future. They cannot be invoked, you have to convince them. Once you have, their involvement with you will not be accidental or a random favor; they do in their own way care.
There are downsides to being King. One is that Kings can really reign over the life and death of projects and careers, and this can make them feel they’re above or outside society. Kings are quite rare even in the era of crypto-billionaire philanthropy, and so there is a loneliness that comes with their decision-making, and a difficulty of trusting friends and advisors, let alone other Kings. The great fear of the King is that he will be duped or scammed. And it is true that most people want to take something from the King: money, status, a name to drop. Managing these resources and keeping people guessing are talents good Kings have or develop.
The great hope of the King is that he is not “just” a king — but also someone to love like a “regular guy/girl who likes to work out” or a great thinker, or a very charitable person. A lot of Kings want to be a little bit like Priests.
Some Kings of course have successful secondary areas of operation, or can be notable theorists of their field or of society. A great King is on a speaking tour right now about Satan.
(2) Priests
One doesn’t have to go full Faust, though, when seeking a good deal or someone to broker it.
Priests are a very different flavor of mentor, giving a very different kind of permission. If you are a Priest, you may in some cases be giving zero-to-one resources to mentees — but your main function and M.O. will still be about something else.
The Priests — as in our medieval town — are tasked with being present during the great life transitions of mentees and providing practical and spiritual support. One of the great transitions is of course entering the mentorship itself — whether this is an academic program, a grant, an internship. But in the case of a Priest, that is just the beginning, and in many ways the least important phase of the partnership.
The type of permission a Priest gives is the confirmation of the transition as real and legitimate. Especially in our fuzzy times, when we work outside traditional institutional boundaries, these forms of “blessings” are of absolute psychological necessity.
Good mentors, of course, don’t want to interfere or influence mentees badly or in a bad moment and risk doing harm, and so — unlike the medieval Priests who were summoned for obvious births and deaths — this form of mentorship will require a lot of tact, good habits, and good communication.
Using the Priest archetype also helps us see that these mentors don’t themselves preside over life and death itself. They are professional witnesses instead, of the suffering and successes of others. The Priests preside over rites of passage — between life or death, or one life and the next — and their presence confirms those changes have happened.
The downside of being a “Priest mentor” is that Priests will have a lot of information about other people. This is both a mental and emotional burden to bear, and — paradoxically — having too much information about people can make later decision-making about them more difficult, not less (How talented is somebody you have seen at their most untalented? Kings only see our A-game, Priests see everything.)
While Kings have undeniable resources to impart with, Priests gain their legitimacy from — us. We give it to them. And so the relationship between Priest mentors and their mentees is always less … shall we say “violent”? Priests didn’t take their power, we gave it to them. We appointed or at least accepted them as intermediaries between ourselves and some higher aim, our better selves. And so these relationships always, already, start in implicit agreement, they’re by default much more equal. (I’ve always seen American politicians — and great standup comedians — as being the “Preacher” archetype, and maybe this is indeed where the Tocquevillian harmony between elective democracy and religion is the most archetypically obvious.)
It is very hard to tell whether you are a King or a Priest as a mentor — because as a King you want to be more like a Priest and so you will develop some priestly activities and behaviors, and because as a Priest you might be distributing some resources yourself. But other people around you will know which type of authority you are immediately, they can sense it, they respond to it... Then, when people don’t get what they came for, there might be disappointments, so it is always good to give this question some thought.
A great mentor I know recently told me when I congratulated him on a new, exceptional mentee: “I am just guarding the exit.” And I thought, well, that is just not true… Because I distinctly remembered how five years ago he was asked to join the beginning of an Interintellect salon hosted by a then up-and-coming female scientist — to be a witness. To confirm, with his presence, that some change had taken place, that she was now a public intellectual to listen to. There was no external reason for this confirmation to be needed: the room was full, there were newcomers and well-known people who all loved her and came for her. But it was the mentor who had to see her, the act of seeing confirmed her transition — and I was a witness to this witnessing! — otherwise the transition would not have felt complete, indeed it would not have happened. And that is not a one-off act of gatekeeping, but a continuous testimony of Bildung. (I know we always come back to Hegel — here: how recognition by another person moves individual self-consciousness to the next level — but this is how it is.)
Priests are terrified people will drag them into their lives against their will. I think this fear is mostly unwarranted. While I don’t mentor people officially outside my own mentoring program, in Interintellect, as the leader, I often act as a Priest. I am summoned for life transitions. I have more information about people than I ask for. It is a recurring source of disappointment when a salon host secretly hopes I would turn up for their salon, and I don’t. (Often they don’t tell me; they want to see if I will do it by myself.) And still, as in a real clan, while I might be sent drafts or be called in a crisis, most people who think of me as their mentor take pride in delineating a life where they don’t need my permission anymore, which is solely theirs. And, funnily, very often I’ll be the last person to find out two members or hosts in Interintellect are dating, collaborating, or have just had a child together. For me, as long as I know about problems first, this is fine.
And sure, there might be some innovative marriages that make daily use of their wedding officiant, but most people prefer to leave the Priest at church, and only call upon him for christenings and deaths, or during illness or marital problems. And so it is with Priest mentors, although respecting their worries and boundaries is probably a good idea.
*
After discussing all these circumstantial dichotomies influencing how mentorship works and what it can achieve, now we will address perhaps the most important human polarity, that between men and women.
Obviously, there is a LOT going on between men and women, in mentorship and anywhere else, and so even trying to scratch the surface is an impossible undertaking.
So to give this some contour, I am not going to talk about some of these — multiple book deals worthy —complications…
The media portrayal of male and female mentors
Whether in a masculine field like tech a mentee is better off with a male mentor vs a female one
Cultural differences
That both men and women have both feminine and masculine traits that can react to each other in a variety of combinations that have nothing to do with chromosomes
Whether the man or the woman or both being parents affects their mentoring behavior; whether the sex of their child/ren matters
Gay men and women, vs straight, whether sexual orientation matters
When couples collaborate in a mentorship-like way, whether gay or straight
How it used to be “back then” vs how it is supposed to be now
The cases where mentors and mentees hook up
About the patriarchy (sorry)
Instead what I’d like to do is a very cursory comparison of same-sex vs man/woman mentoring duos, because I think there is something very important there.
(1) Same-sex mentorship
Women in tech like to complain that most mentorship in our field is between men and men. All the podcasts, all the famous mentoring duos, all the infamous CEOs… Publicly too, men clearly promote each other more, often as a way to make themselves look better, more “in the know”. Despite many individual male players’ laudable efforts, the game theory simply does not benefit female outliers, the same way as some other fields — like American literary fiction — are female-led and imbalanced against men.
In response, some women turn to all-female mentoring groups, which to some can be an empowering experience, although I am personally always careful with attempts to create parallel realities. (There is a reason why my own mentorship program is called “The GrownUp Table”. That is where you want to sit.) I am — always and forever — hopeful that men and women can work it out. I believe good mentorship can be an important vehicle for that.
Working it out starts with an understanding that in the clan-like, primitive yet spiritual world that is mentorship, both the purpose and the underlying structure of same-sex vs man/woman setups are very different. There might be rare exceptions to this, but people — in any situation — remain people.
In a same-sex mentoring duo, which in my world is mainly man-to-man, the product of the creative partnership is the mentee. The older or more experienced person will build a relationship with the entrant that resembles a parental or elder sibling bond. Together, mentor and mentee create an increasingly better, more maturely expressed version of the mentee, and this growth in confidence and mastery benefits both parties. The mentor can be proud of his creation — and perhaps happy for a new friend — while the mentee can see themselves develop in the desired shape of the role model, the master.
The upside of same-sex mentorship is legibility. The other person is not so much Other: there is a mutual sameness which makes communication and guidance easier. Paradoxically, however, similarity also magnifies the differences between the two people (age, location, status). And so the shadow of the same-sex setup is the potential for rivalry and hatred. Being of the same sex but further apart in age tends to have a positive effect on male-male mentorships, age being a neutral differentiator.
But even when the darker emotions are kept at bay, sameness always threatens identity. To this, most commonly, the mentee might respond with some kind of revolt. A need to redefine boundaries, a need for divergence, a need to “show it”. The mentor has multiple jobs here: to provide the baseline and the standards, to not feel threatened by the growing expertise of the mentee, to manage disagreements if they arise, and in the less fortunate cases, if the bond cannot survive the tests of rebellion, to let the younger person go.
Same-sex mentorships, or even employee-boss relationships, tap into childhood memories and previous thwarted ambitions quite mercilessly. “I have become everyone’s absentee father,” wrote Mike Ovitz about his male employees in a frustrated moment. I too have fought the shadows of my female employees’ mothers in more than one situation, an instance of transference that clinical psychologists are trained for but that most other people, however professionally accomplished in their fields, are not.
And if the older person projects too much of their own “younger self” onto their protégé, the younger person’s self-distancing might be seen as outrageous, a betrayal. One more reason to build mentorship as a form of friendship, where really the ultimate goal is reaching a more equal state of collaboration where these potential former traumas and current expectations can be leveled.
(2) Man/woman mentorship
Despite the easy horrors of the Freudian world model, most man/woman mentorships are neither incestuous nor parental. They are just what they are: a relationship between a man and a woman. The good news is that this setup is naturally more equal: men and women are Other to each other, both strangely attractive and in most ways illegible. Their differences are so great that it weakens even the most forbidding hierarchy — a bit like if two aliens were meeting from different planets and trying to establish each other’s social status back home.
Unknown is equal to unknown — regardless of net worth, compute, or cryonics. I do respect my male seniors but not in the same way and not for the same reasons why a male mentee would. When men and women meet, they always break rank, they always upset the Order. Women might glance wistfully at the mobility implied in any man-man apprenticeship, but it is we who trigger much greater transgression.
But this intellectual equality — the mutual curiosities of minds at play — must not distract from the fact that mentorships, like all other important relationships, are played out on a wider stage, in society, where outcome does depend on access, and where women almost always start with a handicap.
When the mentee is a young woman, this imbalance can be extremely challenging — if not altogether discouraging of association — and something an older male mentor must at all times take into consideration (because the young woman can’t do too much about it). Mentoring a young woman must always include the part where she is taught strategies of dealing with this imbalance.
When the mentor is an older woman and the mentee a younger man — unless the female mentor deliberately wants to be seen as maternal and the mentee is on board with that — the relationship will be more formal than in male mentor <> female mentee setups. This is because the way the younger man can avoid looking like he’s somehow sexualizing the relationship (which of course he is) is by showing a respect so rigid to the woman at all times that it would entrance even Confucius. In my experience this can be loosened up a bit once a friendship element is added to the relationship; when the female mentor makes a deliberate effort to show communality and camaraderie. That said, younger men sometimes “practice” their social graces on their female mentors, and I think there should be a place in life for such rehearsals. (And there aren’t many.)
If younger men are afraid of sinful thoughts then younger women are just afraid, period. It is a sad fact of society and perhaps our biology that hyper-intelligent and super-talented young women are always a thousand times more terrified and less confident than the boys in the same age group, even though the boys are quite often, at that age, less competent than the girls. An older male mentor therefore has to deal with both this internal condition in a young woman and the external conditions of a world that dismisses her intellect and achievements while she may not yet have the skills to fight back. Being closer in age or life-stage has a big positive effect on mixed-sex pairings whether standalone or within a clan-like group.
Unlike in same-sex setups, in a successful mixed-sex pairing the creation is never the mentee. A man/woman relationship is by default creative, generative — fertile. And so the creation that is being created here together is always a third thing, outside the two people.
In more casual cases, the third thing can be just the relationship itself, in a dialectical way. In more elaborate, more mature collaboration setups, the man and the woman will create work together.
When the mentee is female and collaboration for some reason does not happen, I think that is hard on the relationship, and especially painful for the woman, as if the relationship was infertile (“You don’t like me enough?”), or somehow not blessed. To put it bluntly, men and women have to regularly make work-babies, or else there will be problems, and eventually the woman will leave. And likely go find someone else who will be productive with her.
The powerful inspiration that is sparked between men and women is where a lot of societal stresses, industry injustices, and past paranoias can simply … dissolve. In this realm of transformation and vulnerability, often one person can rebalance a lifetime of distrust.
Around the Shabbat table, where men and women gather to create their future, we call every man every great man before and after, and every woman every great woman before and after. And so it is in encounters of talent, excellence, and creativity where each of us gets a new chance to represent and realign the interests of our sexes and make something new together, something that never existed before, outside ourselves.
When we talk about a meeting of the practical and the spiritual, the shared creation of a future that men and women are capable of together is not so bad an example.
Awe
It is of endless annoyance to the philosopher how the most important things in life prefer to elude comprehension. You take the finer phenomena of existence and try to describe them, and it feels like you’re attacking a bundle of bluets with a hatchet. (Is this why composers happened?) You try to pin words on good things and they just slip out, disappear… JOY is a good example: while sadness can be explained for hours and hours (and hours and hours), happiness likes to not even be mentioned. How polite!
And still, there is no joy without the “Superior Man” frequenting his friends for discussion and practice. We need to talk! The mastery of the hands and soul requests cultivation. Culture. Whatever is hard to grasp or put into words by myself, in exchange — the two lakes! — might become obvious. It gets permission.
By now you might have noticed that, when in doubt, I like to find a lucrative contradiction, and massage it until it yields some kind of a solution. Just look at my company: Interintellect. It is — as my friends call it — “applied philosophy”. An oxymoron if I’ve ever seen one! And yet, something caught between those contrasting forces keeps churning out gold. It blurts out truths! Somehow it works despite everything.
The first idea of Interintellect came to me in 2014, when I was a postgrad student at Goldsmiths in London. I’d always been both an artist and a person who can’t help building and organizing things, and it bothered me to see how unsupported the talent around me was. So I built a framework where talent could support each other, via a matching marketplace —
This idea was called “Lightclock” (because I was already great at giving my creations catchy names). The light clock is a thought experiment proposed by Einstein to visualize time dilation. It features a photon bouncing between two mirrors in space, which in certain visualizations reminded me of the computer game Pong. It was a visual symbol of mutuality, of conversation. Back — and forth. Lakes of light.
Then a lot of bad things happened in my life which threw me off course, and I didn’t go back to being able to build anything at all until the fall of 2016. I’m specifying this date because I think it matters when a person enters an industry, what the conditions are like at the time. It will determine the entrant’s baseline as well as their starting-pack community.
I had been in tech on and off since 2010, but it was a side job for me, a pastime. In late 2016 it became clear that it would become my primary career. There were things about tech that came as a total revelation to me. It felt less political (lol), more meritocratic, less sexist (still!), more objective in its judgment, and much, much less zero-sum than the worlds of art, media, and academia that I lived in until then.
I entered at a time when Marc Andreessen ruled a platform called Twitter. We were discussing Nick Bostrom’s Superintelligence. Sam Altman re-announced “E Pur Si Muove”. Zuckerberg was dragged in front of Congress. The IDW was nascent. Jordan Peterson was controversial but mostly sane. When you operate outside traditional institutions, cohorts matter. And so in my “graduating class” were people like Amjad Masad and Packy McCormick (both now investors in Interintellect). Jim O’Shaughnessy’s podcast was up and coming (another investor in my company). Quillette was up and coming. Jason Crawford was figuring out what to do with this progress thing… David Perell was amassing followers. Julia Galef posted regularly. Sahil Lavingia kept surprising people. Hip City Reg distanced himself from the race discourse. Maria Salamanca started helping immigrant founders in new ways.
In my circles, people talked a lot about aspiration. Tyler and Michael Nielsen declared the great ROI of raising other people’s ambition. Agnes Callard wrote repeatedly about it. I remain deeply convinced they are correct. In fact, I feel like the whole Girardian thesis breaks down in the question of aspiration, this more or less inexplicable drive inside individuals which I think resists mimesis. Sure, you might copy other people’s way of being ambitious, but the drive itself — what level of ambition you wake up with every morning — seems totally innate to me, an internal condition, maybe the internal condition of humans.
I think about this maybe more than other people because it is a mystery to me how my own personal ambition could avoid being broken, no matter what happened or how much anybody tried. And how that whole thing works... The human will. And where it comes from. I just don’t know! This makes me quite certain no one else knows either.
People sometimes ask if Interintellect is a talent development program. If it is about aspiration. And I always pause because… Sure, in some sense it is. On our platform, event hosts hone their skills, grow their reputations, their income.
But I am finding myself much more fascinated these days by inspiration. The mysterious ways in which people move and affect each other. Why somebody ends up not being a stranger. Why they speak to you and you can hear it and you want to respond.
You can aspire to anything you want in this life. If no one is inspiring you, your lake will run dry.
Inspiration > Aspiration
Aspiration, in my personal experience, might aim for the best of things, and still it comes from a dark, small, ugly place. There are hurt teenagers huddling in there, interns who were passed over for the job. There are dirty misunderstandings broiling in there, breakups, lost games, petty remarks, fears of an Apocalypse, and siblings who outperformed you at school. In aspiration there is always encoded a deprivation, a despair, an inability to deal with crises head-on. “I need to do this to feel like a person…” Nobody aspires from a happy place.
Inspiration throws the light on us. It catches us by surprise through another person’s mind, their brilliance, their presence. To our shock, they can see us too, and they don’t turn away. If aspiration is the long tail of the past, then inspiration insists on the present and sees us capable of a future. In inspiration, we learn mutuality, and that we’re not so bad at all. It is being a person to a person as default whole.
Aspiration is audacious because it crosses a boundary — in my aspiration I go further inside or from myself, I cross my own line. Not stopped by anyone, I can end up doing great harm, violence to myself.
Inspiration is audacious because it breaks someone else’s boundaries — it dares to come closer to another and cause change. Since the license is mutual, the crossings can be more tentative, more exploratory, more measured. In inspiration, no one has to hurt themselves or the other.
In mentorship, a special type of mutual inspiration, we seek formative, chosen suffering to become better — and we find betterment not in suffering but in JOY. I wonder if it is inspiration that takes us from one to the other.
Whatever heights I might reach through my aspiration, I am constantly put back into my place by the sheer fact of my not understanding the Other. I am taught, again and again, not that I know nothing, but that I know no one. And in inspiration, I can accept this. Inspiration is mutual ignorance and mutual learning. Hope.
We might assume that from this total illegibility of other people emanates all human belief in God. From this mystery comes all art as a way of saying: I don’t understand, but I want to! Here is my take —
Being of the same cohort, being loyal to the same mentors, honoring our clan-like arrangements — these things help solve the contradictions of inspiration. The mystery of mutual affection. In the book The Dawn of Everything, Wengrow and Graeber discover that the average human can hold a thought in their brain for about seven seconds. When in conversation with another person: indefinitely. Every major relationship is thus a major, multi-decade conversation. We face each other and keep asking each other the same question. A life spent asking is a life not wasted.
Inspiration between individuals is as much more interesting than aspiration as there are possible combinations between aspiring individuals. These inspired combinations are a billion times more unique than any individual genius could be. And so I take my contradictions and create these loops so something more refined, more original can pop out. Maybe what we call “ethics” is just these loops, and a system that can keep them safe and running.
Inspiration is where our joy starts and where it returns. When I think connection + curation, I think: a good life.
*
During our dinner, a friend asked: Could an LLM be her mentor? And I started wondering about the role of imagination here, of solitary inquiry, unmet expectation.
Zora Neale Hurston wasn’t the only one to have realized her mentor may not have been as active at the whole mentoring thing as she had imagined. Given the confusions around the category and the general intellectual complexities involved, some groups or duos indeed may never be able to openly decide if they are mentorship or not. I believe there are many of us milling about being at least partly mystified who our mentors are and whom do we mentor. For public profile mentors and mentees, it can be even harder to tell.
The most personally harrowing econ paper I have ever read found that women tend to “overestimate the amount of altruism shown toward them”, even in the most intimate settings like families. I found it harrowing because it touched upon a real problem: that in male-first environments such as my job, women have to negotiate unique deals with people and try to shut out the rest of the world in order to get anything done, to build a real relationship — but in the real world out there things continue to unfold in their usual proportions. And so we can see that we are not really a part of it, never really inside. (And I do get it, men are just so, so much easier to help, and to help at scale — and the market wants to specialize.) And so I think in some fundamental way women can never really be sure. We never know if we’re just imagining the goodness or kindness of somebody, or if it’s real. And from our inquietude theoretical systems emerge that can then be helpful for everyone.
One way to be sure would of course be building one’s own separate reality, one’s own clan and law, and giving up on the joys of bridge-crossing collaboration with Others. But that’s more like an evasion of the problem than solving it. Like I said, parallel world-building is always a questionable undertaking. It never answers the original question.
Agnes in her book Open Socrates — an exploration of the ethical system that is conversation — jokes that no matter how detailed her imaginary dialogues with her husband are, when she actually asks him the same questions in real life, he always says something unexpected that she didn’t see coming, something that she couldn’t have imagined. And so I too wonder if I would be satisfied with just imaginary conversations. Imaginary mentors. Imaginary advice. If my lake would be just fine, if it would replenish itself… If, like when I was a troubled young woman, I could just flee to the library, and return to a more solitary, more one-sided life, maybe invoke some meh muse... There would be less pain, less uncertainty, less vulnerability for sure. Less fear of being deceived, or feeling like one can’t tell.
Then I remember the JOY.
You know, I too used to think it was suffering that made people better, but now I am not so sure. Maybe the poets lied. I think the Fool knew.
I’ve come to think it is happiness that makes us better — we have to evolve and stand up to the task of never losing it. In joy, the contradictions and differences somehow evaporate and then we have to deal with …. not being divided by anything. It is the most contrarian of all knowledge. That inspiration runs both ways and there is nothing there to stop it. That it can turn into … anything.
And so I stand my ground day after day, and try to contain it all. Imaginary or not — muses and mentors. I am accepting the fact that the highest ROI in fact is having people in one’s life whom one never ever want to let down. Ever.
I think this is what good mentorship does, to both mentors and mentees. Like all great friendships it shouldn’t work, but it does.
What a great pleasure it is for me to come to this piece on a weekend morning. Your writing is rich, thanks for sharing this.
Oh wow it’s quite a piece and I realize as I flow into it I almost don’t recognize the subject matter at all. This isn’t a criticism of the piece just that it so foreign to my lived experience in the first section of the work. This is a reflection more a reality of how I experienced the Great American Sort and the profound traumas of ripping & reforming that make nearly American without steady foundations (anyone not in the top 10%) immigrants and foreigners in their own land as the remake themselves to survive and thrive.
I’ve not been been mentored in a meaningful way. I’ve found little interest from others in helping younger generations (with rare exceptions like Jim O, my first startup CEO & my first corporate ceo) and have largely found that America is a country of self creation and in our particular moment absolutely everyone in the older generations of X and above have profound disdain for the troubles & struggles of those millennial and under because it would require too much responsibility for them to admit the failures they allowed on their watch.
I say this despite myself having dedicated quite a bit of time to the mentorship of my own portfolio founders because of this experience of disinterest but have also found ultimately that their acts of self creation hinge little on formal categories of help and rest entirely on the soft gentle presence of someone who believes in them and that’s it.