Don’t Surround Yourself With Smarter People

There is an idea that I have been guilty of uncritically parroting and promoting in the past: surround yourself with smarter people. Another popular version is never be the smartest guy in the room. 

Beneath the humblebragging  in both versions (your cut-off for smart is a de facto declaration of “look how smart I am; only Einsteins are worthy of surrounding me, and I understand the things they say!”), there is a basic logical issue: If the smarter people are dumb enough to surround themselves with the likes of you, they are dumber than you, which means they’re smart and you’re dumb. Wait. What?

This is not just a cute paradox, it’s a fatal Godel-level error that crashes the whole smarmy idea. The only way to make it work is hypocrisy: adopt at least a double standard (and preferably an n-standard, where n is the number of people) for “smart.” You’re street-smarter than me. But I’m book-smarter than you. And our friend over there is potato-smarter than both of us. This is the juvenile stuff of folk tales, caper movies and self-consciously different band-of-misfits superhero coalitions.

Yet, there seems to be a germ of truth to the idea.  My alternative to the heuristic, which many of you have heard in off-blog conversations, is that I am only interested in people as long as they are unpredictable to me. If I can predict what you’ll do or say, I’ll lose interest in you rapidly. If you can keep regularly surprising me in some way, forcing me to actually think in unscripted ways in order to respond, I’ll stay interested. It’s reciprocal. I suspect the people with whom I develop long-term relationships are the ones I surprise regularly. The ones who find me predictable don’t stick around. We’re not talking any old kind of surprise, but non sequiturs. Surprises that you can’t really relate to anything else, and don’t know what to do with. Mind-expanding surprises rather than gap-closing surprises.

Huh?! rather than aha! or ooh!

So smarter isn’t the word here (even though there’s one definition of smart that’s close to “unpredictable”). Neither is different. I can often predict the behavior of smarter and/or different people of both unconventional and conventional types. The trick is to surround yourself with people who are free in ways you’re not. In other words, don’t surround yourself with smarter people. Surround yourself with differently free people.

That’s going to take a bit of work to unpack.

Freedoms of Degree and Kind

Differently free implies a difference in kind rather than degree, but let’s deal with differences of degree first.

At its simplest, freedom is a binary variable. You’re either free or you’re not. That’s often good enough for people in a condition of gross non-freedom, like slavery.

A slightly more refined view is to think in terms of totally ordered degrees of freedom, allowing people to be ranked from most to least free. A queen is strictly more free than a castle. In any chess situation, replacing your castle with a queen will certainly do no harm, and almost always do some good. Going the other way is guaranteed to not improve anything, and will almost always do some harm.

Any sort of swap-out in this kind of strict freedom hierarchy has deterministic effects on one side of the space of possibilities and probabilistic effects on the other side.  In other words, replacing a piece with another in such a hierarchy has one determinate effect: it either makes things semi-strictly better or it makes things semi-strictly worse (semi- because things remaining unchanged is an admissible possibility).

A more refined view is to view freedoms as unique capability patterns. Two behaviors that are by definition uniquely free  cannot be arranged in a strict order of more and less free. A castle is generally more powerful than a bishop, but not strictly more free. It is constrained to move along rows and columns and cannot move along a diagonal. The power disparities can be very high: a queen is far more powerful than a knight, but still not strictly more free, because it cannot do those L-shaped jumps on the chessboard.

This means that swapping pieces has an indeterminate effect. Swapping a queen for a knight almost always makes things worse, but in some small fraction of situations, makes things better. You can’t know for certain though, unless you specify the situation and compute the resulting change in positional strength.

This is still a difference of degree rather than kind though. We just replaced a more deterministic notion of degree with a more probabilistic one.

For those with more freedom in a given situation, the challenge is always the challenge of the queen contemplating an unknown piece. Is it a rook or a knight? Someone you can assuredly feel superior to in any situation, or somebody who might, in some situations, be superior to you? If so, do you prevent those situations from occurring to maintain your power (authoritarianism), or do you encourage those situations, to increase systemic capabilities at the expense of your own absolute power (pluralism)?

We haven’t defined differently free yet, but we’ve gotten closer. We’ve gone down a slippery slope from an absolute notion of freedom to a relative notion. Once freedom becomes a probabilistic function of situation, and agents can control their situation to some degree, freedom becomes a relative notion.  There are justifications available for abandoning authoritarianism and seeking pluralism and more freedom for all.

We’ve opened the door to true differences of kind. A knight is almost differently free from a queen.

Freedom to Win

The chess metaphor is deceptive. It accepts the goal of chess uncritically as a given. Queen and knight are not truly differently free because they share exactly the same  definition of win.

Freedom is therefore implicitly freedom to win in a specific sense. This is not an accident. Any time you define freedom in terms of capacity for action (intrinsic and situational), you’ve defined freedom in a finite-game (Carse) way. Increasing freedom becomes a matter of increasing your capacity for victory over increasingly capable opponents, until you’ve defeated them all.

Stated another way, freedom to win is freedom to get smarter in the sense of a given finite game.

Freedom in a finite-game sense is always freedom-to-win (and therefore, freedom to stop playing at some point).  That’s the conclusion Sam arrived at two weeks ago. You graduate and level up to a qualitatively different finite game; one that requires you to start again at the bottom and learn and refine a whole new set of skills. You may or may not enjoy rollover-manna from the previous game.

There is a problem with this level-up metaphor though, which I coincidentally pointed out in The Adjacency Fallacy in a different context: life viewed as a series of exits from “lower-level” games to “higher-level” games is still a finite game, because you’re still playing to win in an expanding but consistent sense. Higher-level victories don’t change the value of lower-level victories. They build on them. This keeps status evolving predictably. It doesn’t matter whether it is a zero-sum game (others must lose for you to win) or positive sum( others can/must win for you to win). It’s merely a multi-level video game instead of a single-level board game.

You may be alive to the current game level, but a pattern of leaving games only to smoothly transition to the next one actually leaves you in a finite game in the Carse sense. You’re never not playing to win. You are only taking extra time on occasion to decide what is worth winning next that will also preserve the value of what you’ve already won. This is purposeful introspection rather than a true liminal passage. When you don’t have a purpose, your purpose becomes defining the next purpose.

When you’re in freedom to win mode, you’re constantly focused on improving your position, capabilities and odds of winning. You are always evaluating strategies, and making up clever lines of attack or defense. The activity that glues the rest of your activities together is keeping score. This is clearer in poker and investing than in chess. In poker, unlike chess, due to the inherently probabilistic nature of the game, technically perfect game-play can still lead to a loss, so players of those finite games make sure they keep two kinds of score: actual wins/losses, and a separate score that measures whether or not they played correctly, whatever the outcome.

This separation of technical score-keeping and outcome score-keeping leads to a more dangerous place: score-keeping becoming sufficient to sustain finite-game mindsets even when the game is ambiguous or unclear, and there is no agreement among players about what the goal is. Money is the classic example of a mechanism for keeping score that is divorced from outcomes.

Make as much money as possible, as fast as possible, for as long as possible is a finite game, defined purely by a score-keeping mechanism.

When you have a hammer in your hand, everything looks like a nail is also a finite game, the one played by those with a strong professional identity.

What might it mean to play an actual infinite game, where the purpose is to keep playing?

Freedom to Keep Playing

Let’s switch gears a bit, since freedom to keep playing is a very different beast. We’ll connect the dots in a minute.

I’ll define freedom to keep playing as a domain-specific ability to see reality in unsentimental ways, and act on reality in appropriate ways.

Appropriate needs some qualification. I don’t mean socially appropriate, technically appropriate or somebody else’s idea of what’s appropriate in a given situation. I mean in the sense of the zen idea of the ripples in a pond in response to a tossed stone being appropriate.

The stone-in-the-pond metaphor describes behaviors that are neither under-reactions, nor over-reactions, nor irrelevant or superfluous in relation to the situation. The pond is your mind and the ripples are your subjective experience of what you’re doing. The ripples are completely determined in a physics sense, but paradoxically, are completely free in a subjective sense. You suffer no anxiety due to dissonance between expectations and reality. There are three principal components to this non-dissonance:

• Knowledge: In part this sense of freedom is due to knowledge: you’re less torn by anxious attachments when you recognize how something must naturally and necessarily unfold. If you fire somebody, they’re going to be upset, and if you know that ahead of time, you can be all pond-like about it. Knowledge is freedom from getting mad at facts.
• Detachment:  Detachment does not mean you don’t care what happens. It just means you don’t care whether a specific thing happens or not. You want to know the outcome of the coin-toss (you care), but you don’t care whether it is heads or tails even if you’ve bet on heads (you’re not attached to a specific outcome). The important thing is that something happens, which means you’ve successfully kept play going, but without keeping score.
• Emotional Self-Management: I like to think of this as accepting the emotions you have instead of having emotions about having emotions in an endless stack. Yeah, the tooth is about to get painfully pulled. Fear. Not fear, plus anxiety about fear, plus guilt about anxiety about fear, plus shame about displaying guilt about experiencing anxiety about having fear. This is emotional focus. Instead of retreating from an emotion through layers of additional emotions until you find one you can deal with, you experience the actual emotion for what it is.

That’s probably the order of difficulty in building up your capacity to keep playing.

The image this adds up to is not one of preternatural equanimity, but force of nature. The Incredible Hulk is actually a good example of stone-in-the-pond. He’s just a very big pond capable of handling boulder sized provocations without emptying out.

When you inhabit your own behaviors this way, you get creative. You have enough surplus attention to notice bits of reality that are non sequiturs in relation to the finite game you are in.

This is why dispassionate perception plus appropriate action equals freedom to keep playing: they enable you to create a space where ways to keep playing become visible. This excellent two–part cartoon exploration of depression cuts to the heart of this phenomenon. Without spoiling the ending, I can safely reveal that the non sequitur in the story is a piece of corn.

How do you know it is a non sequitur? Your prevailing freedom-to-win does not suggest any engagement of it because nothing you can do to it, or that it can do to you, changes the score in your prevailing finite game. Your mind literally has nothing to say about it, hence the silence and emptiness characteristic of the cognitive space that a non sequitur inhabits. At the same time, the non sequitur is an opportunity to expand the current game by changing it, or switch to a new game.

It exists in freedom-to-keep-playing space rather than freedom-to-win space.

The presence of a non sequitur in your awareness means your attention is not oversubscribed with finite-game emotions and thoughts competing for room. There is a residual emptiness that can be occupied by the unexpected without being roughly shoved out by things that matter.

The non sequitur piece of corn in the depression story is an example of what I call a parrot. Freedom to keep playing is mental room for parrots.

If freedom-to-win leads to an economics of pricelessness, freedom-to-keep-playing leads to an economics of worthlessness. A good literary image to keep in mind is my favorite Lord of the Rings character, Tom Bombadil. The one person both unaffected by the One Ring, and immune to its power. To him, it is philosophically worthless in the sense of a parrot, a non sequitur that can exist without a value being attached to it.  This is not the same thing as a finite-game idea of worthlessness, which is simply zero in-game value.

Freedom to win strives towards an ultimate win defined by an equilibrium of pricelessness: a utopia. Freedom to keep playing, on the other hand, is a Bombadil-like equilibrium of worthlessness: the un-valued here-and-now. You can move freely and naturally through it. Smooth and striated become one. Piece-of-corn and piece-of-gold have no necessary relationship to one another.

This equilibrium is a naturally unstable one. The trick to getting there is not being afraid to fall out of it. This is why children are good at it. When everything is a toy, everything is at once worthless in the infinite game and priceless in the finite game, because its worth can be a function of how you’re playing with it. In one game, an empty cardboard box can be priceless and an expensive doll worthless. In the next game, the roles can be reversed.

But once you grow up, you become afraid of losing yourself in a finite game because you lose the ability to stop playing.

The Courage to Fall Asleep

Why is it useful to define freedom to keep playing in this way?

Because any time one or more of the three conditions defining an equilibrium of worthlessness is violated, you trigger a chain of events that end with you becoming immersed in some finite game and oblivious to it. The obliviousness is a sort of falling asleep, a loss of the awareness that you are in a finite game.

When you lose awareness that you’re in a finite game, you lose the ability to change it, and mistake freedom-to-win for freedom-to-keep-playing.  You lose the ability to see parrots. No Kobayashi Marus for you, says the Game Nazi.

This does not automatically mean you’ve lost the freedom to keep playing, since winning in  finite games is also a way to continue playing. For a while. But finite games, by definition, exhaust themselves at some point, either by ending in time, or by you outgrowing the finite freedom-to-win that they offer.

So at least on the surface, there is a relationship of mutual exclusion between freedom-to-win and freedom-to-keep-playing. To gain one is to lose the other, just as to gain sleep is to lose wakefulness. To play a finite game obliviously, you must become blind to parrots. Or  gorillas. The technical term for this is inattentional blindness.

Corresponding to the three elements of freedom-to-keep-playing, there are three basic ways to fall asleep, which can be combined.

1. Seeking knowledge of any sort is hard. Accepting ignorance of any sort with finality is one way to fall asleep.
2. Seeking detachment is harder. Conflating skin-in-the-game and head-in-the-game is another way to fall asleep.
3. Seeking to experience a primary emotion is hard. Retreating to a more manageable emotion is the third way to fall asleep.

Anecdotal aside: in my experience, the most common way to fall asleep is the third way, which makes sense since it is also the hardest part of freedom-to-keep-playing to practice. The most common emotion people retreat from is some sort of identity insecurity. The most common emotion people retreat to is simmering resentment towards those who provoke the insecurity, which often drives a complex redemption-and-revenge life story.  Great things can result from such stories. (aside: now that we know who Nassim Taleb is, I know who I am.)

Whatever the trigger, the result is a crash-like descent into a finite-game sleep that unfolds like so:

1. Violation of any equilibrium-of-worthlessness condition creates expectations of value.
2. Expectations lead to score-keeping. Freedom-to-keep-playing is replaced by freedom-to-win.
3. Score-keeping and freedom-to-win leads to privileging of some behaviors as as more worth-while (notice the time-value connotations of the term).
4. Privileged behaviors — capabilities embodying freedom to win —  induce definitions of game skills and win conditions.
5. Definitions of game skills and win conditions create explicit finite games with associated notions of utopia and pricelessness.
6. Explicit finite games make the world a legible place and blind you to things that are not part of the game.
7. Blindness to the non-game worthless makes you incapable of changing the game.
8. Inability to change the game makes you oblivious to the fact that it is a game.
9. Once you are oblivious to the game, you cannot see parrots.
10. Once you lose the ability to see parrots, you lose the ability to keep playing when the finite game ends.

For want of  a tiny corner of mindfulness, the infinite game is lost.

Such descent into sleep is typically triggered by consumption addictions, attachment to a capability (role identity, the mask becoming the person) or attachment to a group identity. But I’ve rambled on about those things for years now, so I won’t repeat myself (too late?).

If this crash-like process is inevitable, recovery is not.  If you happen to become aware of a parrot in time, like the piece of corn noticed by the author of the depression story, you can regain the ability to keep playing.

But if you crash into a finite game and fail to see a parrot for long enough, you can lose the will to keep playing entirely. What makes this suicidal outcome much more likely is thinking of waking up from the finite-game sleep as a skill.

Where there is no notion of worth, there can be no notion of skill. There can be nothing to optimize or perfect.

Awakening from a finite game is not a skill, let alone one you can perfect. It is not something you can train for. It is not a finite meta-game with its own score-keeping system (“Hah! I am Enlightenment Level 4 with 23 Mega-Buddhas of consciousness. I can awaken from a Purple Hazard finite game with just a parrot. You’re only Level 3, you’d get killed even by a Green Hazard finite game even if you had a bald eagle!”).

When you begin thinking of awakening as a skill, you become afraid of falling asleep. Where awakening is a skill, falling asleep becomes an act of courage.

Philosopher’s Insomnia

The ability to lose yourself completely in a game as an adult, to the point that you’re oblivious to it, requires great talent for that game. As an adult engaged in skilled play, you face the risk of never awakening even when the game cannot continue.

There are many who recognize this deep risk, and develop an existential fear of it. The possibility of falling asleep into a finite game and never waking up becomes so fearful, they react by self-sabotaging every path of talent development before it gets too far along.  This is cultivation of an extreme generalized incompetence at life is a defense mechanism against the threat of oblivion presented by finite games.

I call this philosopher’s insomnia. A fear of falling asleep cause by fear of never waking up from a finite-game dream. It is, of course, a fear of death in disguise. Every fear is a fear of death in disguise.

Ironically, insomniac philosophers can become so skilled at avoiding developing their talents, they can end up as what Scott Fitzgerald called “the most specialized of all specialists: the generalist.” That is perhaps the hardest finite game to awaken out of.

So philosopher’s insomnia doesn’t actually work as a defense mechanism. If you don’t turn the cultivation of incompetence itself into a game of skill, some other finite game will invariably suck you in. When it comes to insomniac philosophers at least, every finite game is an adverse selection mechanism: it sucks in precisely those insomniac philosophers who are least alive to the fact that it is a game, and therefore most susceptible to falling terminally asleep within it. By definition, the game that sucks you in is the one that you are not on guard against.

I never thought I’d be making a living writing. During my sleepless years, I was never on guard against writing. By the time I realized what was happening, it was too late. I was already halfway decent at it.

It comes as news to most people that they can get very skilled at playing games without being aware of it. A skill is something we normally think of as requiring a great deal of careful, deliberate practice. Those kinds of games are in fact the minority. The most common kind of finite game is the kind you fall into without noticing.

This is also why philosopher’s insomnia does not work. There is no general way to be incompetent at every finite game, just like there is no general vaccine for all infectious diseases. Some  incompetencies you are born with. Other things you have to learn to suck at.

The ones you don’t notice, those are the ones you might get good at accidentally, without realizing it. Some day I hope to learn to fly by accidentally missing the ground. I am just waiting for the right kind of non sequitur surprise.

Awakening Predictably, by Accident

We can finally define what it means for someone to be differently free from you. They are people who are playing just a slightly different game than you are. That difference makes them a reliable sources of non sequiturs in your life.

Waiting for nature to present you with a parrot or a piece of corn to awaken you out of a finite game is a tricky, chancy business.

Differently free people change the equation in an interesting way. When you include a person in your life, it is because they have a definite worth (possibly negative) in whatever finite game you’re asleep in at the time. This means there is at least some overlap between their game and yours; some similarity between how you keep score and how they do. Some meaningful relationship (possibly adversarial)  between how you define winning and how they do.

This means you have a model of the person in your head. One that predicts how they will value things.

But it is the parts that don’t overlap that matter. There are things that have a defined worth in their lives that are non sequiturs in yours, and vice versa. When you see through the eyes of a differently free person, you expect to see a landscape of presumptively valued things. A landscape based on your predictions of how they value things. When the other person appears to value something that doesn’t even register with you, for a moment, that thing turns into a non sequitur, a candidate parrot. It lingers just a little bit longer in your own mind than it would if you yourself saw it. Long enough that you do a double take and notice it consciously.

Most of the time, you’ll just update your models and valuations in an in-game way and move on.

But once in a way, the moment will snap you out of your finite game and put you in infinite-game mode.

(this is also the moment that the other person becomes a person rather than a model in your head, graduating from an it to a thou, but that’s another story)

The partial, imperfect overlapping of two finite game freedom-to-win fields of view can accidentally trigger a freedom-to-continue-playing moment for one party. This, I think, is the logic behind Wiio’s Law: communication always fails, except by accident. And that’s the reason it’s worth surrounding yourself with differently-free people: to use the law of large numbers to turn such accidents of communication into a certainty of awakening from any finite game you might be asleep in.

Once you can do that, it takes no courage at all to fall asleep.