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Smart People Vs Interesting People, The Pause State, & Why You Can Afford to be Nice

Resource: Don’t Surround Yourself With Smarter People (Venkatesh Rao)

“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.”


The admonition to surround yourself with people who are smarter than you is an overrated and ambiguous cliche. The underlying intention is clear (ie. try to hang out with people who make you better), but emphasis on smartness has its weaknesses. A better (or perhaps cooler?) approach is to focus on surrounding yourself with people who are differently free than you.

To be differently free is not a matter of having more/less power, but a matter of being uniquely distinct in terms of how you define the experience of winning. One person can define winning in terms of having lots of money while another may define it in terms of being close to family members. Person A may be richer than Person B and therefore more free as it pertains to financial things, but since Person B is playing a different game with a different definition of winning, they are differently free not more free.

Two entities can be differently free even when one is more powerful than the other

When a person is differently free than you, they have behaviors and beliefs that show up as surprising in your world of experience. Differently free people are reliable/rich sources of non sequiturs. They don’t just say interesting things that generate aha moments. They say things that create temporary patter interrupts. Sometimes these pattern interrupts can snap you out of a finite game.

A finite game is one where you play to win. An infinite game is one where you play for the purpose of continuing the game. The goal of a finite game, even if you happen to run out of time before reaching it, is to bring the game to an end in some kind of way. Infinite games are all about perpetuating the play.

“Finite games play by the rules. Infinite games play with rules.” -James Carse

Playing to win is a finite game. Playing in order to be free from having to play is a finite game. Even a spiritual goal like achieving enlightenment is a finite game.

People who are differently free usually have some overlaps with us when it comes to the finite games we play, but the part that makes them differently free is the surprising ways in which they define winning in the finite games they play or the manner in which our finite games are non sequiturs in their world.

Matters unresolved, questions for further exploration, and/or resources to follow up on:

Are infinite games necessarily better than finite games or is this way of evaluating them itself a finite way of thinking?

Rao’s reference to “one definition of smart that’s close to ‘unpredictable'” -

Carse’s Finite & Infinite Games might be worth rereading soon.

Interesting looking article referenced — Playing Games to Leave Games —

Rao referenced an article he wrote on thinking in unsentimental ways:

“This excellent two–part cartoon exploration of depression cuts to the heart of this phenomenon.” —Part 1: and Part 2:

The Economics of Pricelessness –

Rao on “head in the game” versus “stake in the game.”

Rao on Crash-like thinking

Three other interesting pieces from this excerpt — “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?).”


Being Unpredictable > Being Smart

“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.”

Surround yourself with people who are differently free from you rather than people who are smarter than you:

“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.”

On how two entities can be differently free even when one is more powerful than the other:

“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.”

Understanding Freedom in the finite game sense:

“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)…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.”

Freedom to win is a finite game:

“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.”

Freedom to keep playing as an infinite game:

“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.

Defining the appropriateness of infinite game behavior:

“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.”

The 3 components of non-dissonance (appropriateness):

“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.”

Inhabiting the playful and open space of infinite games:

“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. 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.”

On keeping room for the unexpected in your mind:

“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.”

On being differently free:

“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.”

Differently free people are rich sources of non sequiturs:

“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.”

Resource: Existential Psychologist Rollo May on Freedom and the Significance of the Pause


To be free is to have the mental wherewithal to maintain composure and engage the world with intentional responsiveness even when in the presence of varied stimuli. To be free is to be firm, constructive, and deliberate when your circumstances would rather have you be overwhelmed.

Pausing is an essential element of the free life. When you pause, when you take a break from your roles and identity attachments in order to be mindful, you make direct contact with the very context of your freedom. <—- This reminds me of the biblical passage that says “Be still and know that I am God.” Stillness — the pause state to which Rollo May refers — is the space out which apparently divine possibilities arise.


Rollo May on Freedom as internal composure and intentional responsiveness:

“Freedom is the capacity to pause in the face of stimuli from many directions at once and, in this pause, to throw one’s weight toward this response rather than that one.”

Rollo May on the pause state and how it opens us to freedom:

“The pause is especially important for the freedom of being, what I have called essential freedom. For it is in the pause that we experience the context out of which freedom comes. In the pause we wonder, reflect, sense awe, and conceive of eternity. The pause is when we open ourselves for the moment to the concepts of both freedom and destiny.”

Resource: Why It’s Safe for Founders to Be Nice

“Startups usually win by making something so great that people recommend it to their friends. And being rapacious not only doesn’t help you do that, but probably hurts.”


Being nice refers to the practice of being unrapacious in your collection efforts.

Your growth rate is a greater indicator of profitability than your collection rate.

Focus more on making moderatly appealing products great than anything else.


Why being unrapacious in extracting money from your users is less costly than startup founders think:

“Suppose your company is making $1000 a month now, and you’ve made something so great that it’s growing at 5% a week. Two years from now, you’ll be making about $160k a month. Now suppose you’re so un-rapacious that you only extract half as much from your users as you could. That means two years later you’ll be making $80k a month instead of $160k. How far behind are you? How long will it take to catch up with where you’d have been if you were extracting every penny? A mere 15 weeks. After two years, the un-rapacious founder is only 3.5 months behind the rapacious one.”

Why your growth rate is more important than your collection rate:

“If you’re going to optimize a number, the one to choose is your growth rate. Suppose as before that you only extract half as much from users as you could, but that you’re able to grow 6% a week instead of 5%. Now how are you doing compared to the rapacious founder after two years? You’re already ahead—$214k a month versus $160k—and pulling away fast. In another year you’ll be making $4.4 million a month to the rapacious founder’s $2 million.”

Why a lack of growth, not a lack of collections, is usually the real problem:

“The other reason it might help to be good at squeezing money out of customers is that startups usually lose money at first, and making more per customer makes it easier to get to profitability before your initial funding runs out. But while it is very common for startups to die from running through their initial funding and then being unable to raise more, the underlying cause is usually slow growth or excessive spending rather than insufficient effort to extract money from existing customers.”

Advice for startup founders who fear being too nice:

“So if you’re a founder, here’s a deal you can make with yourself that will both make you happy and make your company successful. Tell yourself you can be as nice as you want, so long as you work hard on your growth rate to compensate. Most successful startups make that tradeoff unconsciously. Maybe if you do it consciously you’ll do it even better.”

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