This is a short essay on plans, written on a delayed Metro train. I originally posted this on Facebook randomly, then cleaned it up and posted it at http://ammarmian.com/posts/on-plans.html. Will probably post most things over there from now on. Posting here for redundant archiving.

What is effective is not the same as what seems effective.

We often do things that make us feel effective, whether or not that action actually is effective.

Thus there is effective and "effective".

We make plans, and it is up for debate whether we are making them to be "effective" or effective.

I argue that we are rarely aware of this distinction and are often acting in "effective" ways.

Many plans we make, inherit, and adhere to may be "effective" or effective, we're not really sure, because our only measure of the value of a plan or action is if it feels effective.

Put in other words, we fixate on clever or noble plans, ignoring entire classes of plans that might actually be effective but don't necessarily make us feel great.

The Insecurity of Not Knowing

So what is this feeling? It seems like before we can even try thinking of how to be effective (without quotations), we need to know why we are drawn to being "effective" (with quotations).

Desiring feelings of effectiveness may derive from a root insecurity about our own abilities to handle uncertainty.

We want to show that we have something figured out, and we want to listen to those who show they have things figured out. Otherwise we just say we're not cut out for one thing or another.

It's a very simple way to deal with uncertainty -- either show that you're fully certain, find someone who does claim that, or don't involve yourself at all.

Due to this insecurity over our ability to deal with uncertain terms, we fixate on making (and listening to) "effective" plans -- plans that feel like certitudes in some way or another.

This is why we get so excited by clever exercise regimens or diet plans or learning modules or stump speeches. If we fail, it's because we just weren't cut out for it. Not because the plan sucked (which it did). Because just look at how clever and fancy the presenter was!

An Attempt at a Better Plan

Over the past four years I've tried and failed and succeeded and failed and failed and failed and failed at coding, teaching, writing, marketing, reading, thinking, taking standardized tests, snowboarding, running, meditating, etc.

I've noticed the most effective plans take one general shape:

1. Diagnose
2. Explore
3. Diagnose again
4. Make a short term schedule
5. Follow it studiously
6. Repeat 1-5

Steps 1-3 take the most time and constitute the most emotional work because each time you enter, you're not quite sure if you'll make it out to step 4.

But then you repeatedly do.

This is the act of learning over and over again what it means to not be sure of how things are. This is a crucial element of solving problems, it appears, to somewhat masochistically cherish the unknown unknowns.

During this process, you may figure out you hadn't ever really precisely defined what you were trying to do.

And then it turns out you were your own limit.

And then it turns out that the concept of you is flexible.

And then the real fun work begins.

From psychologist Hoye Leigh's Genes, Memes, Culture, and Mental Illness:

"Primitive memory formed by trial and error died with the organism. With the evolution of complex brains, however, memory in the form of brain codes acquired the ability to skip from one brain to another, first by imitation as a shortcut to trial and error, and later, with language, as knowledge and information. When memory achieved portability, it became memes, bits of replicating information."

From philosopher Friedrich Nietzsche's Human, All Too Human:

"Twofold misjudgment:

The misfortune suffered by clear-minded and easily understood writers is that they are taken for shallow and thus little effort is expended on reading them.

And the good fortune that attends the obscure is that the reader toils at them and ascribes to them the pleasure he has in fact gained from his own zeal."

For many people, 2016 was the year of hurt. Over the past few months, this has been the prevailing thread in many long conversations I've had with friends. Below I attempt to distill these conversations into a single essay.

---

Despite our efforts, we cannot help but to hurt each other, especially when the stakes are so high.

At first I wondered if it was just an inevitable part of being human. But that seems too lazy of a conclusion. That's the conclusion that leads to jaded sorority girls writing about relationships on Elite Daily, weary intellectuals ruminating about a godless existence, and radicals waging war in the name of Some Party You Aren't Invited To. That's no fun.

The way we hurt ourselves and each other stems from a poor understanding of how our thoughts, desires, and memories work. 

These three streams are what we absorb most willingly, and they converge to help us form a notion of who we are (our ego). The ego is a useful construct because it helps us have a semblance of continuity and consistency.

But the ego also has a dark side -- it often deludes us into believing that our thoughts, desires, and memories are valid and correct. We thus fail to be thoughtful, to listen carefully, and to avoid passing our pain on to others.

A lot of the violence we commit happens silently and without even noticing ourselves doing it. This habitual violence is so deeply ingrained, it's nearly impossible to eradicate it entirely. I keep catching myself sliding into these ego-fueled patterns. So the best thing we can do is to begin to understand what they are and what they look like.

From law professor and metaethicist Ruth Chang's On Hard Choices:

"As post-Enlightenment creatures we tend to assume that scientific thinking holds the key to everything of importance in our world. But the world of value is different from the world of science. One world can be quantified by real numbers, but the other cannot.

We shouldn’t assume that the world of is, of weights and lengths, has the same structure as the world of ought, of values."

The Red Pill, The Blue Pill

My siblings and I have watched The Matrix together more times than I can count. We spent most of our time seeking out hilarious out-of-context two-second snippets that we would play back over and over again. Yes, Vine a full fifteen years before Vine.

Anyways, the soul of the entire movie lives in one scene. Morpheus presents Mr. Anderson with a red pill and a blue pill:

"You take the blue pill, the story ends. You wake up in your bed and believe whatever you want to believe. You take the red pill, you stay in Wonderland, and I show you how deep the rabbit hole goes."

Viewed in isolation, neither option is superior in any obvious way to the other. Both are, as Ruth Chang would say, "on a par" with each other, though leading to uncertain and diverging outcomes. The red pill would show Mr. Anderson a world outside The Matrix. Or it might not. The blue pill would allow Mr. Anderson to return to his life as usual. Or it might not. 

To different people, different decisions would be appropriate in this situation. But as viewers, we know Mr. Anderson will pick the red pill because we already know what his values are. We already know from earlier scenes that he is a rebellious, dissatisfied fringe member of the corporate world. With that emotional context laid out, we know exactly which decision he will make. We might even be rooting for him to choose one way.

"This type of response to hard choices is a rational response. But it is not dictated by reasons given to us. Rather, it is supported by reasons created by us. When we create reasons for ourselves to become this kind of person rather than that, we wholeheartedly become the people that we are. You might say that we become the authors of our own lives."

Reasoning & Emotions

In his influential Descartes' Error, neuroscientist Antonio Damasio describes the peculiar circumstances of a patient named Elliot. A brain tumor caused damage to Elliot's frontal lobe; subsequently, his ability to experience emotion evaporated. In the ensuing years, Elliot's professional and personal lives unraveled, as he found it difficult to make decisions.

We sometimes tend to think that the best decision-making system is one that is purely rational and devoid of emotion. But in Damasio's estimation, reasoning is incomplete without emotional motivation. Many decisions cannot be reduced down to choosing between less, more, or equal quantities. We might even think we're being entirely rational, when really a suppressed emotional context might be invisibly creating this appearance of rationality.

Hard decisions are hard because there is no correct answer to them. If the decision was easy, there would be no dilemma. My eternal dilemma is: should we go get noodles or tacos for dinner? I don't know! Both options sound amazing!

What makes hard choices is the set of tradeoffs and uncertain futures that accompany them. One set cannot necessarily be proven "greater than" the other. We can use measurement to get as close as possible to an objective view of these tradeoffs, but at some point, the uncertainty of correctness still remains.

In this space of difficulty, the agent must observe this decision in terms of the system that is her life. By choosing one alternative over another, she has made a normative choice as to which types of tradeoffs, uncertain futures, and new realities she is willing to accept. Over time, these normative choices form our notions of principles and character. And when we feel like we've made a mistake, we can go back to the drawing board and re-evaluate how we decide. As Chang says herself:

"[...] the reasons that govern our choices as correct or incorrect sometimes run out, and it is here in this space of hard choices that we have the power to create reasons for ourselves to become the distinctive people that we are."

Hypothetical: Jobs (and Investing in Anything)

Here's a hypothetical about deciding between job offers (because that's something I'll be doing pretty soon). Choosing a job, like most choices dealing with a degree of uncertainty, involves an investment. Generally speaking, investing is the act of choosing one uncertain future over another, with the hope that a particular subset of futures comes to fruition.

You can minimize uncertainty through observation and data, but at the end of the day, all uncertainty can't be vanquished. In fact, an over-reliance on measurement might even blind you from some uncertain outcomes you hadn't anticipated.

The typical approach to the job question is to choose the most socially validating job in your community. Another approach is to enumerate pros and cons for each option and then pick the job that's the biggest net positive. Both methods on their own can quickly lead to unhappy outcomes when faced with hard choices. Prestige-bound choices occur through forces external to the decision-maker, while exhaustive pro-conning can act as a form of fake rigor.

A more robust approach would be to envision the person you are and the person you aspire to become. What are the values and principles that ought to be guiding your decision? Which job offers would prevent this person from actualizing? As a good friend recently pointed out, something as simple as a bad interview experience could point to such a misalignment. 

A valid thesis could be: I want to construct a life in which 1) I nurture strong relationships with family and friends, 2) I devote my energy to mastering a craft, and 3) I have the right time-money balance to dedicate to missions I care about. As thoughtful decision-makers, we can go through each of these levers to clarify exactly what they mean and what they look like. Why are they so important to us? Do we fear the things we value?

Introspecting like this can show us the types of biases and insecurities we are susceptible to. Maybe we lean to the safe and prestigious at the detriment of what we actually need. Conversely, maybe we ignore the option we need precisely because it is safe and prestigious.

Principles, Values, and Science

A principles-based analysis often creates a simplifying rigor to decision-making. It eliminates enticing offers that would jeopardize your values. It illuminates options that you may have been hesitating to take seriously.

Of course, this is not to say that striving for purely rational thought is stupid. In fact, many areas of our lives can be better understood through this form of reasoning. You can "science the shit out of" more things than not. In some cases, you can even science the shit out of analyzing your own values.

But in the realm of decision-making, scientific rigor should exist in the service of identifying and acting upon principles. We see this everywhere: sports (the Broncos and zone blocking schemes, the Spurs and ball movement), software (Amazon's maniacal focus on the customer and near-100% uptime), organizations (Google's super analytical approach to hiring and preventing bias); politics (Denmark's rehabilitation-focused counterterrorism efforts) ... the list goes on and on.

In the long run, a well-tuned set of principles can give an entity a pretty long-lasting advantage over its peers. Mostly because everyone else doesn't have the patience to act based on principles.

Perhaps the most concise expression of all the above comes from the philosopher king Kanye West:

Damn, here we go again.
Everybody's saying what's not for him,
But everything I'm not made me everything I am.

From Sebastian Junger's Tribe: On Homecoming and Belonging:

"Humans don’t mind hardship, in fact they thrive on it; what they mind is not feeling necessary. Modern society has perfected the art of making people not feel necessary."

"Unlike criticism, contempt is particularly toxic because it assumes a moral superiority in the speaker. Contempt is often directed at people who have been excluded from a group or declared unworthy of its benefits. [...] Contempt is one of four behaviors that, statistically, can predict divorce in married couples. People who speak with contempt for one another will probably not remain united for long."

From EF Schumacher's A Guide for the Perplexed:

"Map-making is an empirical art which makes use of a high degree of abstraction but nonetheless clings to reality with something akin to self-abandonment.

Its motto, in a sense, is 'Accept everything; reject nothing.' If something is there, if it has any kind of existence, if people notice it and are interested in it, it must be indicated on the map, in its proper place.

Map-making is not the whole of philosophy, just as a map or guidebook is not the whole of geography. It is simply a beginning - the very beginning that is at present lacking, when people ask: 'What does it all mean?' or 'What am I supposed to do with my life?'"

I remember when I started loving maps. It was when I first learned that the map we see in schools is actually a projection (the Mercator projection) rather than an objective representation of the world. In reality, the United States neatly fits into the Sahara Desert; the Indian subcontinent is larger than all of Western Europe. Yet the Western rendition of history makes these "exotic locales" seem so insignificant.

Point being, maps are great. They show you where everything is, but they can't show you every thing, and so "everything" becomes an editorial decision. What makes the cut? What is worth looking at? The arrangement and centering of a map also tells you what the mapmaker thought was most important (notice how Mercator's projection placed Germany longitudinally in the center of the map).

Iterating on the Design of Mental Maps

"It's easy to make perfect decisions with perfect information. Medicine asks you to make perfect decisions with imperfect information." 

From Lewis Carroll's Alice's Adventures in Wonderland:

"[Alice]: 'Would you tell me, please, which way I ought to go from here?'

'That depends a good deal on where you want to get to,' said the Cat.

'I don't much care where--' said Alice.

'Then it doesn't matter which way you go,' said the Cat.

'--so long as I get somewhere,' Alice added as an explanation.

'Oh, you're sure to do that,' said the Cat, 'if you only walk long enough.'"

From Slavoj Zizek's Plague of Fantasies:

"The original question of desire is not directly 'What do I want?', but 'What do others want from me? What do they see in me? What am I to others?' A small child is embedded in a complex network of relations; he serves as a kind of catalyst and battlefield for the desires of those around him."

From Anthony Storr's Solitude: A Return to the Self:

"Many of the patients whom [a famous psychiatrist] treated had, for one reason or another, learned as children to be over-compliant; that is, to live in ways which were expected of them, or which pleased others, or which were designed not to offend others. [...] This is what Winnicott deemed a 'false self' -- that is, a self which is based upon compliance with the wishes of others, rather than being based upon the individual's own true feelings and instinctive needs. Such an individual ultimately comes to feel that life is pointless and futile, because he is merely adapting to the world rather than experiencing it as a place in which his subjective needs can find fulfillment."

During the summer between my freshman and sophomore year of college, I flew off to Aix-en-Provence for a 10-week study abroad program. For the first time in my very sheltered life, almost every pillar of protection had been knocked over. 

All the self-defense mechanisms I had carefully cultivated over the years wouldn't work here:

• The program consisted of 2 boys and 40 girls; I had attended an all-boys prep school for ten years.
• The local culture was very expressive and open (a lot of kisses, touches, and proximity); I had a pretty conservative upbringing in a stoic Pakistani Muslim household. 
• People in Aix didn't speak much English; my French was "academic" -- great for probing analyses on Voltaire, but little practical value.

As a result, during my first week in Aix, I subsisted off of a Nutella-and-bread diet, holed up in my room watching Amelie in darkness. I exercised the only semblance of control I could find -- stick my head in the ground.

Eventually, I realized what was going on with me. Many of my unconscious habits of disengaging with uncomfortable situations had now become not only alarmingly conscious, but also ineffective. I feared going out to the market to grab groceries or start a conversation with a stranger because I feared how my errors in French or other quirkiness would negatively impact how others viewed me. Even if they couldn't care less.

The Fear of Social Rejection

This is a pretty common setup for the College Kid Abroad narrative. The "immersion" aspect throws him (or her) for a loop; he leans into the awkwardness; lingual and personal transformation ensues. He returns with a Mediterranean tan, a chiller, slightly arrogant demeanor, and new clothes/music. Or maybe he doesn't lean in and has a miserable time.

Why does this happen? We can look at some psych literature for some clues. In his excellent book Others in Mind, Philippe Rochat asserts that self-consciousness is a modern syndrome in which the "self is an object to itself co-constructed in interaction with others."

"As a species, we are caught in a unique and fateful reflective loop. We have the privilege as well as the curse of being able to reflect upon ourselves, as an object unto itself, but also through the eyes of others."

In other terms, I create an idea of "Ammar" largely in relation to other people's recognition of me. When we sit with friends and talk about random things, on one level, yes, we're engaging in friendly banter and love. But we're also exploring and experimenting with our sense of self by mutually recognizing each other and actively being aware of the existence of each other. We are simultaneously constructing others and being constructed by others.

Rochat writes that a side effect of this "co-constructive" feature of being human is a hard-wired fear of social rejection. When social encounters make someone anxious, it may be because he fears that others will see him unworthy of recognition. This is a case of believing that others are actively constructing and de-constructing the person, as opposed to all of this being a shared, cooperative activity. 

Some of this is genetic, but much of it is environmental -- if you've been raised to view your sense of self coming from certain accomplishments (and that most of your human interaction with others revolves around discussion of said accomplishments), then of course there will be anxiety about not being "good enough" for others. If you feel your self driven by other people's expectations of you, then at some level you fear their rejection (and thus lack of recognition) of you.

This process of co-construction could also be why we: act differently around different people; enjoy being regulars at coffeeshops or delis or bars or restaurants; feel comfortable in small groups but lose footing in crowds; say things like "I'm so glad I met someone who's as weird as I am"; join cults.

Getting Out of the "Comfort Zone"

Over time, the way we deal with this constant co-construction becomes habituated and subconscious. My relationship to myself and to others stabilizes, so then I get a person named Ammar who generally is x and does y and thinks z.

Going abroad shatters this habituated self and brings all of this to the conscious surface. There are no comfortable nooks you can reliably crawl back to, no previously saved versions of You that other people agree upon. Every encounter is a potential source of social rejection -- if not because of your quirkiness, then definitely because of your broken French. 

Being abroad (or generally speaking, being thrown way out of your comfort zone), you have to consciously re-address your relationship with this co-construction. Will you play an active role in exploring the different ways you can experience yourself and experience others? Or will you passively accept the easiest version of yourself that others expect you to be?

How to Travel Well

A large part of traveling is really a way for your "self" to travel, to be thrown out of the context of the self it has been habituated to be.

Traveling well is to harshly reacquaint yourself with the fact that you are a constructed You (and that you have the power to construct that person however you wish).

Traveling well is also realizing that how you treat other people (or even things and places) is also constructing them. There is a responsibility in not only compassionately constructing yourself, but also compassionately constructing the people around you.

In this sense, traveling well doesn't necessarily require a passport or a sexy Airbnb apartment rented out in Havana. You can travel well by more actively participating in co-construction: brunch with friends, conversations with Uber drivers, hikes, long walks. Though that Cuba trip does sound pretty awesome.

From Sufi scholar Zia Inayat Khan:

"Wisdom is the fruit that ripens when, with crazy courage, we plant ourselves in the garden of radical unknowingness. It is the deep breath that accompanies the willingness to not know, to rest in the mystery, to abide in surprise and allow the sacred to reveal itself in its terrible beauty and startling ordinariness. To be wise is to come undone and pay attention to the dismantling and celebrate what rises from the annihilating depths of love’s fire."

Lately, I've been reading a lot of works by Sufi scholars. One of the most profound ideas that constantly reappears among their teachings is the notion of secrets. Hidden truth. Wisdom that is not visible until the beholder is ready to see it. This type of understanding is not rational; it does not appear simply by being present and logically coherent.

The idea of hidden truth is embedded in the very mechanics of Sufism's patron language. Mostly every word in Arabic takes shape from an algebraic combination of three consonants. The pattern in which they are combined often give them their meaning. 

Let's take a look at the various combinations of Q-L-A (Anglicized to make it easier to follow):

• There's the verb qalla, which means "to become less" or "to diminish".
• And there's the adjective qaleel, which means "a little (amount)" or "small (in quantity)".
• But if you change it a little, to istiqlal, now you have the word for "independence".
• One more slight alteration, and you get istiqlaliyyah, which means "self-reliance".

You can see how generative, poetic, and suggestive a language gets when small and almost unnoticeable alterations yield potentially great differences in connotation and meaning. Especially when you as the observer bring your own specific experience to the table.

One person may hear qaleel in istiqlal -- to be independent is to diminish the self. 

Yet another person may hear istiqlal in qaleel -- to become less is to become independent.

Maybe there is equal meaning in both, but we cannot unlock the true duality of meaning until we are ready to see and feel it.

The Fable of the Four Travelers

The Sufis are all about this concealed beauty to things. One fable that illustrates this principle really well is Idries Shah's story about the four men in search for food.

"I want to buy angur,” said the Persian.

“I want uzum,” said the Turk.

“I want inab,” said the Arab.

“No!” said the Greek,  "we should buy stafil.“

Another traveller passing, a linguist, said, "Give the coin to me. I undertake to satisfy the desires of all of you.”

The traveller buys them four small bunches of grapes. They realize that they had each wanted the same thing -- grapes. The disharmony had been caused by their faulty understanding of each other. 

Even deeper still, in Sufism, the juice of a grape steeped with time is the wine of wisdom. But before the wine can be tasted, the man must first learn to recognize the grape as a grape.

Modern Grapes

In these modern times, our "grapes" of misunderstanding exist within ourselves. Oftentimes, when we feel something is missing from our lives, we seek out a surface-level acquisition of something.

For some, that may be material things. Buying the newest and the hottest. Quality by association.

For others, it might be knowledge. Reading voraciously but not deeply. Looking to extract wisdom from other sources rather than seeing these sources as vehicles for extracting wisdom from the self.

Or maybe it's something like relationships, or prestige, or money, or some other indicator of success. 

All of these amount to a faulty understanding of what we're really missing.

Becoming the Indiana Jones of Secrets

So what do we do to find what we're missing if our current model doesn't work? Hunt secrets. Silicon Valley investor Peter Thiel, trained in the works of philosopher/secret-hunter Rene Girard, has written about secrets for years. In his Zero to One essays, he wrote:

"Every great business is built around a secret that’s hidden from the outside. A great company is a conspiracy to change the world; when you share your secret, the recipient becomes a fellow conspirator."

In the realm of business, this makes sense. Airbnb rediscovered the secret link between homes, intimacy, and lodging. Uber rediscovered the secret of car pools. Pixar rediscovers time and time again the power of ancient stories retold with new characters.

Perhaps every great self is also built around rediscovering secrets that are "hidden from the outside." Finding these secrets of the self is not a formula, but once you start seeking them, small innocuous seeds of experience get much more interesting. Nothing is boring anymore. And slowly that vague feeling of modern emptiness might just start to dissipate.

From ecologist Garrett Hardin's Filters Against Folly:

"The greatest folly is to accept expert statements uncritically. At the very least, we should always seek another opinion. Moreover, to the extent that time allows, we may become a little bit expert ourselves; but we don't have time enough to go far in this direction. 

[...] We need lay defenses against expertise. Fortunately there are such. The most important defense measure is to make oneself sensitive to the biases introduced by the assumptions and methods of experts."

Around this time of year, many of my friends participate in the weekly ritual of lifelong connection and sweet everlasting Platonic love (or whatever), huddling around a friend's HBO Go subscription and watching the latest episode of Game of Thrones. I always get asked if I want to watch, but truth be told, I really do despise the show. Maybe I'm just salty that I don't get invited anymore.

"Why? I thought it'd be right up your alley?!"

I hate the British accent. That's my only reason for not watching the show (that, and I also dislike medieval costumes).

Let me back up a few years.

During my freshman year at Georgetown, there was a guy (let's call him Hugh) in one of my international relations classes. He had made a name for himself for his deeply insightful commentary. It was as if his every word dragged against a charm-soaked silk on its way out of his mouth, producing this Oxford-cultivated je ne sais quoi.

Every time Hugh spoke, you could feel everyone kind of perk up from their hangovers and pay attention. I definitely fell for it.

One day, though, I wondered how I would respond to Hugh's words if he had a different accent. So I started transcribing his words, going to the library later in the evening, and then quietly reading them out in different accents (sorry, I'm pretty weird).

It turned out that there was very little substance to what he was saying. The "insights" we had thought he had been bestowing upon us were largely a stream of multisyllabic smart-sounding jargon -- "neoliberal thought," "postcolonial constructivist narratives," "tectonic shifts in global political theatre," etc.

Much of what he was saying could have be distilled to "People are angry at the British Empire and don't know what to do with themselves."

The Milgram Experiment

Years later, in a psychology lecture I occasionally showed up for, the professor mentioned an experiment that enlightened me on what had happened in the Case of Hugh the Bullshitter. In situations of uncertainty or moral confusion, we tend to seek out and abidingly listen to what appear to be authority figures.

Back in 1961, a Yale psychologist named Stanley Milgram conducted a role-playing experiment in which "teachers" were told to administer electric shocks of increasingly high voltage to "learners" who didn't answer a question correctly. Unbeknownst to the teachers, all the shocks were fake, and the learners were all actors pretending to get shocked.

At some point, these "shocks" approach an absurdly high voltage, and the actors started screaming in anguish. Many of the teachers, unsure of what to do, shifted nervously in their seats and muttered some quiet words of criticism.

But the experiment runners told them to continue. "It is absolutely essential that you continue." "The experiment requires that you continue."

So at the behest of the experiment runners, an overwhelming percentage of the teachers continued administering these electric shocks. 65% of the teachers escalated the shocks up to the maximum voltage that the experiment allowed.

Obviously, there are many interpretations of what the Milgram Experiment observed. But one big thing it revealed was our natural inclination to listen to those who, through language and circumstance, behave like authority figures.

This is scary on many levels. But the scariest is that we unquestioningly and unwittingly defer to authority on a daily basis. In fact, many of us young ambitious types working in professional services end up mimicking and adopting the very behaviors of the people who have used language to bullshit us.

(I'm not saying to never listen to experts. But real experts typically don't cloak their work in impenetrable fluffery).

I've witnessed this in my 4 years since graduating from college. People who were at some point smart, thoughtful, and careful thinkers have in many ways degraded in the way they communicate, now monkeying the language of their bosses (for profit, social-climbing, and some pleasure). I can't say I haven't fallen victim to this myself.

Three Types of Bullshit

So let's examine what I think are the three forms of bullshit that we encounter every day (whether at work, or in school, or on TV).

1. Notational
2. Linguistic
3. Ritualistic

Notational Bullshit

Mathematical notation plays an important role in building, explaining, and representing models. But the notation itself can easily become a form of unnecessary authority-signaling.

For example, that notation above looks pretty sweet and beautiful and intelligent, but it's really just expressing a very simple idea: "Given a list of ice cream flavors (A) and ice cream toppings (B), give me a list of all the different ways these flavors and toppings can be combined with each other."

It's succinct and elegant, but there's no reason to put too much value on the notation itself. Just because someone knows how to use linear algebra to notate combinations/permutations doesn't say much about his competence in being insightful about them.

We saw this in the startup world a couple years ago when people were going bananas about "viral coefficients". Notationally, this looked like this:

But really, all this is alluding to is "For every one invitation to my app I hand out, how many people actually sign up for my app?"

Fucking simple. You don't need notation to explain that. If your product is awesome, then 1 invitation will lead to the invitee signing up, then inviting all of his friends, most of whom also sign up. If your product sucks, then your one invitation will lead to 0 sign-ups.

But getting obsessed with the mathematical notation game is a common ploy among nerds like me who derive their self-worth from sounding smart. And it makes outsiders think our tinkering/experimenting is really some intense Hadron Collider-caliber theoretical physics-based shit that requires a lot of technical knowledge. Which it doesn't.

Linguistic Bullshit

Linguistic bullshit is what I call jargon that isn't fulfilling its purpose. Jargon is a domain-specific language used by a group of people to more precisely refer to a shared set of concepts. So when a lawyer says "due process" or "fact pattern," they are referring to an abstraction very specific to their field. When a banker says "LBO", it's a more concise way of saying "these guys bought the shit out of a down-and-out company with plans to change their top brass and flip them years later for a profit." In these two scenarios, the jargon is very helpful.

But here's an example where the jargon is designed to make a simple thing sound much more complex than it really is.

From Basecamp co-founder David Heinemeier Hansson's talk at Stanford, Unlearn Your MBA:

"I have a funny example of how bad things can go when your brain has become all mushy with all this MBA bullshit.

This is Domino's CEO David Brandon talking a few weeks ago:

'The weakness in our value chain with the customer was really in our core product.'

...What?? What does that even mean? Well, I tried to translate that into human, and what I came up with was:

'Let's be honest, our pizza used to suck. I'm sorry. I swear the new ones will be better.'"

Linguistic bullshit, like notational bullshit, is often used to convey expertise (rather than to convey insight or truth). Be wary.

Ritualistic Bullshit

The third, most subtle form of bullshit is the bullshit of ritual: repeated behaviors that signal authority by telling observers that the person knows what he's doing.

Don't get me wrong, rituals are important. In basketball, the rituals that players use before shooting a free throw are crucial to the activation of muscle memory & mental clarity. Morning meditation or journaling or that weird thing you do before an important test/speech/what-have you -- these play the role of getting an individual into the mental space required to perform at a high level.

But contrast these earnest forms of ritual with the following absurdity Dan Lyons describes in his book Disrupted. The CEO of HubSpot brings a teddy bear to every staff meeting, giving it an equal seat at the table, supposedly as a stand-in for HubSpot's customers:

"Here are grown men and women, who I presume are fully sentient adult human beings, and they are sitting in meetings, talking to a teddy bear. And I am working with these people. No: Worse! I am working for them. At Newsweek I worked for Jon Meacham, who won a Pulitzer Prize for his biography of Andrew Jackson. Here I work for a guy who brings a teddy bear to work and considers it a management innovation."

A handful of quotes. I promise they are related.

From Andrew Yang's Smart People Should Build Things:

"If you work in professional services you will be paid handsomely and have a brand-name firm on your résumé. You’ll gain skills, confidence, and exposure. But you may also become heavily socialized and specialized, more risk averse, and accustomed to operating in resource-rich environments with a narrow set of deliverables. You’ll be likely to adopt an arm’s-length relationship with your work. You won’t build anything; instead, you will compartmentalize and put the armor on each day as deals, clients, and colleagues come and go."

" [...]  productive jobs have, just as predicted, been largely automated away (even if you count industrial workers globally, including the toiling masses in India and China, such workers are still not nearly so large a percentage of the world population as they used to be). But rather than allowing a massive reduction of working hours to free the world’s population to pursue their own projects, pleasures, visions, and ideas, we have seen the ballooning not even so much of the 'service' sector as of the administrative sector, up to and including the creation of whole new industries like financial services or telemarketing, or the unprecedented expansion of sectors like corporate law, academic and health administration, human resources, and public relations."

"Evidence of submission is displayed by having gone through years of the ritual of depriving himself of his personal freedom for nine hours every day, punctual arrival at an office, denying himself his own schedule, and not having beaten up anyone. You have an obedient, housebroken dog. [...] (However), there is a category of employees who aren’t slaves, but these represent a very small proportion of the pool. You can identify them as the following: they don’t give a f*** about their reputation, at least not their corporate reputation."

From MIT Media Lab's Alex Pentland, Social Physics:

"One disturbing implication of [our] findings is that our hyperconnected world may be moving toward a state of too much idea flow. In a world of echo chambers, fads and panic are the norm, and it is much harder to make good decisions. This suggests that we need to pay more attention to where our ideas are coming from, and we should actively discount common opinions and keep track of contrarian ideas."

"Courage is in far shorter supply than genius."

Almost every day, a voice calls out to me. He asks me:

Sometimes this voice is another person - a curious friend, an aunt or an uncle, a stranger or old acquaintance. A parent, a sibling. Sometimes it's that voice inside my own head.

I've learned that this voice, bless his soul, is very often full of shit. You see, the honest, correct, encouraging, and life-affirming answer to that question would be:

We're all just making it up as we go along, and then we re-jigger our personal narratives after the fact, in hindsight. "I did this which led to this and that." 

Messy, undefined narratives in the present tense are part of the deal -- they only begin to take on a shape after you reflect and decide that they have a discernible shape. But if you don't have enough source material, there's not enough stuff to reflect on; your only choice then is to keep moving forward and gathering that source material. 

Alas, that pernicious voice doesn't like this state of affairs. He wants reality to be predictable, unchanging, and easy to reason about. So I lie and give him answers like this:

These are the lies we tell to give ourselves some semblance of control. The mystery is now neatly packaged into a trope, a playbook of sorts. The voice receives a nice little dopamine hit, and he leaves satisfied knowing that his game of Jenga lives to see another day.

Vague Graphs as Rorschach Tests

The disconnect here lies in the fact that much of the observable world is a Rorschach Test -- you see what you want to see, and you see it that way until it kills you (or hurts you enough to cause you to see it differently).

So here's a Rorschach Test. I present 7 graphs, accompanied by quotes that you may have heard before. These graphs have in some form made rounds in mainstream business press, but many of them also serve as the foundation for the work of some of the most thoughtful writers of our generation. So they are dense with different kinds of meaning, depending on where you decide to look.

For each graph, think about what strikes you most about it. Then read the accompanying quote. Now what do you think about the graph?

1. The Problem with Averages

"Much of the real world is controlled as much by the 'tails' of distribution as by means or averages: by the exceptional, not the mean; by the catastrophe, not the steady drip; by the very rich, not the 'middle class.' We need to free ourselves from 'average' thinking."
- Some Thoughts about Distribution in Economics, Philip Anderson

"For a soldier trained at West Point as an engineer, the idea that a problem has different solutions on different days was fundamentally disturbing. Yet that was the case ... Efficiency, once the sole icon on the hill, must make room for adaptability in structures, processes, and mindsets that is often uncomfortable."
- Team of Teams, General Stanley McChrystal

"We're taught then when you are given a choice you have to choose only one option. But why choose? ... This multiple-choice approach - if properly managed - can create tremendous momentum. Ideas cross-pollinate. Networks expand."
- Bold, Peter Diamandis

“Most people get stuck at the Local Max (A) because changing strategy in any direction leads to poorer results … You’ve got a very good job as an art director. To do better, you’d either have to move to another firm, move to another town, switch careers or go back to school. And all of them have costs and very uncertain returns, so you stay. […] Local Max (A) isn’t actually that great when you realize that Big Max (B) is not particularly far away.” 
- Seth Godin, author, entrepreneur

"The frequency of correctness does not matter; it is the magnitude of correctness that matters."
- More Than You Know, Michael Mauboussin

“Optionality is the property of asymmetric upside (preferably unlimited) with correspondingly limited downside (preferably tiny). […] If you have optionality, you don’t have much need for what is commonly called intelligence, knowledge, insight, skills, and these complicated things that take place in our brain cells. For you don’t have to be right that often. All you need is the wisdom to not do unintelligent things to hurt yourself (some acts of omission) and recognize favorable outcomes when they occur.” 
— Nassim Taleb, philosopher

"At any given time, the input that is most important to a system is the one that is most limiting."
- Thinking in Systems, Donella Meadows

From Michio Kaku's The Future of the Mind:

"Although consciousness is a patchwork of competing and often contradictory tendencies, the left brain ignores inconsistencies and papers over obvious gaps in order to give us a smooth sense of a single 'I'."

• The artist searches for a medium to create in, the executive guides that search, and the critic only intervenes if the artist and executive are being erratic.
• Ethos: "Express and create at all costs."

Exploratory Door-Closing:

• The artist still searches for a medium to create in, but this time is guided by the critic's discerning eye. The executive only steps in if there hasn't been much action for a while.
• Ethos: "Express in the right way."

Experimental Analysis:

• The critic is trying to understand a novel situation, guided by the artist's expansive view of the world. Again, the executive only steps in if there hasn't been much going on.
• Ethos: "Carefully expand capacity."

Experimental Activity:

• The critic is still trying to understand something new, but he's now guided by the executive's bias for action. This time, the artist sits back and intervenes if the critic and executive are missing something obvious.
• Ethos: "Carefully test the waters."

Purposeful Doing:

• The executive knows what needs to be done, and his striving is guided by the artist's ability to figure out different ways to get something done. The critic sits on the sidelines, looking for cracks in the "this needs to be done" argument.
• Ethos: "Get it done."

Purposeful Planning:

• The executive knows what needs to be done, but his actions are guided by the critic, who make sure nothing gets overlooked. The artist sits on the sidelines, making sure those two aren't exhaustively searching in the wrong place.
• Ethos: "Figure it out."

The cool part is that there's a time and place for each one of these permutations. I feel it takes a pretty self-aware person to be able to comfortably go from one to the other; most of us spend our time in maybe two of these types for our entire life. This leads to "old dog, no new tricks" behavior because when you've found a long-term comfort zone with one type, the other types atrophy.

From Bernard Roth, design guru at Stanford:

"If you have a problem that you're really losing sleep over ... it's because you're working on the wrong problem. (This concept) is what we call in design thinking "Reframing the Problem." The way I suggest you do this is to ask yourself: "What would it do for you if you solved the problem?"

"The player of the inner game comes to value the art of relaxed concentration above all other skills; he discovers a true basis for self-confidence; and he learns that the secret to winning any game lies in not trying too hard."

From Alice Miller's The Drama of the Gifted Child:

"Quite often we are faced here with gifted patients who have been praised and admired for their talents and their achievements ... In everything they undertake they do well and often excellently; they are admired and envied; they are successful whenever they care to be - but all to no avail. Behind all this lurks depression, the feeling of emptiness and self-alienation, and a sense that their life has no meaning. These dark feelings will come to the fore as soon as the drug of grandiosity fails, as soon as they are not "on top," not definitely the "superstar," or whenever they suddenly get the feeling they failed to live up to some ideal image and measure they feel they must adhere to."

• Josh Waitzkin: child chess prodigy, Columbia University grad. Now a Brazilian jiujitsu master and student of the art of learning
• Tim Ferriss: Princeton grad. Now runs the 4 Hour Workweek blog, podcast, and show that he started a decade ago
• Naval Ravikant: Dartmouth grad, dabbled in consulting. Now founder of AngelList & famous angel investor
• Haruki Murakami: Studied drama in college, spent his twenties running a jazz club with his wife. Now a renowned novelist
  
• Ken Jeong: Duke grad, MD from UNC, practicing physician. Now a comedian and actor
  
• Mohsin Hamid: Princeton and Harvard Law grad, former McKinsey consultant. Now an award-winning novelist
• Vijay Brihmadesam: Private equity analyst. Quit his job, worked at Chipotle, then started Tava Indian Kitchen in SF
• James Freeman: Professional clarinetist turned founder of Blue Bottle Coffee
• Demetri Martin: Yale grad, accepted into NYU Law. Now a renowned standup comedian
• Joshua Redman: Harvard grad, accepted into Yale Law. Now a jazz saxophonist and composer
• Ang Lee: Immigrant from Taiwan, famously toiled away on screenplays while his wife supported him. Director of Life of Pi
• Ezra Koenig: Columbia grad, former Teach for America teacher. Lead vocalist of Vampire Weekend
• Rollie Peterkin: Penn grad, Wall Street veteran. Quit his job for MMA training in Peru, now an English teacher in Madrid

I wish there was some data to confirm my suspicions, but I think talented/ambitious people going off-script isn't as risky as it seems to them. It's all in their head. The New American Dream is having the courage to successfully go off-script. Someone once wrote that in life, you get 2 out of the following 3: freedom, certainty, and money. The most common form of striving seems to value the "certainty + money" combination. It'll be interesting to see how the other combinations play out as more people get disenchanted by the standard mode of striving.

From Michio Kaku's The Future of the Mind:

"Although consciousness is a patchwork of competing and often contradictory tendencies, the left brain ignores inconsistencies and papers over obvious gaps in order to give us a smooth sense of a single 'I'."

In most realms of human life, there is a status quo and there is a relationship that individual people have with the status quo. The status quo often has much room for improvement. But enough people have busted their asses and worked hard for the status quo to exist, so they aren't going to let the status quo change so easily. These people are probably awesome, and they probably were the status quo changers once upon a time. That's the thing with "the way things are done"-- even when the way things are done change, they find equilibrium at a new set of ways that things are done.

To protect "the way things are done," the guardians concoct a Kool-Aid: a sweet syrupy drink that is largely water and sugar. This Kool-Aid is offered as a way to help newcomers cope with the inevitable "Why are things done this way?"

"Well, you know, it is what it is, but all we can do is work hard and hope for the best and <insert Kool-Aid here>"

The Kool-Aid is a narrative ploy used to redirect questions and turn them into sermonizing about mission, ideology, and other things that are tough to argue against.

The manner in which one responds to the presence of Kool-Aid is everything. It breaks down like this:

The Three Reactions to Kool-Aid

1. Drink the Kool Aid
2. Reject the Kool Aid
3. Wonder why there is a Kool Aid to begin with

First option: you drink the Kool-Aid. You drink it deeply. It's so sweet and delicious. You buy into the story that is being peddled because you hope that it's correct. Sometimes it is; most times it isn't. The world is rarely simple enough to distill into a tasty beverage, hence why the Kool-Aid is so packed with sugar.

Second option: you reject the Kool-Aid. You spit it out, storm off, and reject anything associated with this Kool-Aid.

Third option: you wonder why Kool-Aid is being peddled in the first place. 

Why are people buying into Trump's rhetoric? Why are people buying Bernie's rhetoric? Why are people telling us that Hillary is more realistic? What is the motivation behind all these different forms of peddling in the first place?

You can ask the same types of pointed questions to Kool-Aid distributors in medicine, tech, education, economics, law, basically any part of life that involves "right" and "wrong" of any sort.

The danger with drinking the Kool-Aid is the same with drinking actual Kool-Aid: the more you drink, the more your body depends on it (Have you every tried cutting all sugar out of your diet? Sugar withdrawal is a real thing.)

The danger with fully rejecting the Kool-Aid is that you become an angsty, tough-to-talk-to bystander.

The danger with questioning the Kool-Aid is that you make enemies on both sides of the fence. After all, by merely questioning it, you legitimize the claims of both the drinkers and the rejecters.

At any given moment, there are probably at least 5 different Kool-Aids a person is actively drinking, rejecting, or wondering about the history/ingredients of. I think these roughly break down into the categories of life that your mind spends most of its time in:

• Career: the sweet, delicious Kool-Aid of a regular paycheck, a suit, and a pat on the back
• Society: the exotic Kool-Aid of "making a difference" 
• Education: the school-sponsored Kool-Aid (t-shirt, lanyard, and bottle opener come for free!)
• Family: the "make you proud", well-adjusted Kool-Aid
• Existence: the "bearded man in the sky" Kool-Aid

Here's a potential rule of thumb: your Kool-Aid flavor of choice correlates with how you like your coffee/tea. I'm a sucker for unsweetened iced coffee with a splash of soy milk. My parents are suckers for sugary, milky, cardamom chai. My most enlightened friends don't drink caffeine.

From Jean-Paul Sartre:

"Everything has been figured out, except how to live."

Here's a common setup: someone flips a coin once. What are the chances that it lands heads?

The reflexive answer is to say "50%", and that of course would be academically correct.

The more skeptical response would be a question: "Is the coin fair or is it rigged?"

Here's the second setup: someone flips a coin 50 times, and it landed heads every single time. What are the chances that it lands heads on the 51st toss?

The reflexive answer might be "pretty high, maybe 75-80%?" Which would, academically, be wrong.

As we know, a fair coin's probability of landing heads or tails is not dependent on what it flipped before. That is, tossing a coin is an independent event. Whether you tossed it 50 times before and got heads every single time doesn't affect the chances of it landing heads or tails that 51st time-- the odds of it landing "heads" is still 50%.

But if you view the flipping of a coin 51 times as a sequential series of events, you get a weird situation indeed. Probabilistically, the chances of a coin flipping heads once is 50%. But the chances of flipping heads two times in a row is equivalent to the product of the probability of heads on each toss, which would be 50% x 50%, or 25%. 

And flipping heads 51 times in a row? The chances are incredibly low (0.5^51, or 0.000000000000004%). On its own, that 51st flip has a 50% chance of landing heads or tails, but the chances of 51 flips in a row being the same face are damn near zero.

So a statistically-minded person would say "The flip itself: 50%. But 51 consecutive heads: 0.000000000000004%." And a skeptic would say "Let me see that damn coin, it's got to be rigged." 

Both of these responses are fair. But all of these responses rely on a certain view of the assumptions involved in the simple flip of a coin. These assumptions can be broadly recognized as:

1. Initial Conditions
2. Launch Conditions
3. Flight Conditions

The strictly academic "flipping a coin" exercise focuses on only a small subsection of these assumptions. Namely: is the coin perfectly weighted? Note that we haven't examined some of the more interesting assumptions, some more outlandish than others. Do atmospheric pressures fluctuate at all in between tosses (gravity, drag forces, etc)? Does the coin land on a surface that favors a particular head? Is the person flipping the coin strangely skilled at controlling his toss? Does the coin have free will? Can the coin change its own trajectory as its being launched and as it is landing? But in our pedantic conversation about this coin, we've only identified consecutivity and coin fairness as the primary movers of probability.

The Hot Hand Fallacy

The same academic focus is used to describe the "Hot Hand Fallacy." This phenomenon is used to explain the case of a basketball player "catching fire" and shooting lights out, seemingly unable to miss. 

When a player has a hot hand, the reflex might be to say that the probability of his next shot going in is much higher than average. He's on fire, and our intuition suggests that there's something special going. But as we saw in the case of flipping 51 coins consecutively heads, the probability of a prolonged hot streak is substantially lower with each additional shot. At the same time, though, if each shot is an independent event, the probability of making the next shot remains the same as it was for every other shot, despite the hot streak. Mind fuck!

There are many more variables at play here that complicate this even further. (Stanford professor Jeffrey Zwiebel discusses some of them in a recent paper.)

First is in "initial conditions" -- has the player been getting more sleep, or meditating; has the team changed its offense in some significant way, or has it settled into its groove mid-season? 

Or in "launch conditions" -- has the player been working with a shot guru and thus reached a breakthrough in the rotation and range of his shot; is the player, now much more selective with his shot selection, more patient with when and from where he shoots; now that he has a hot hand, are defenders double-teaming him or otherwise changing how they guard him? 

Or in "flight conditions" -- is the player in the middle of a West Coast road trip where maybe the weather in the month of March favors his shot; does the height of a hoop in some West Coast arenas vary by a couple favorable centimeters? Absurd, yes, but still worth considering. 

One man's lucky streak might be another's actual, legitimate hot hand. Until defenses grow accustomed and adjust. Or in Steph Curry's case, don't adjust (because they can't figure out how to). A coin flip isn't just a coin flip.

Loaded Coins

The point of all this is that maybe there is a way to game a fair coin. There are probabilities that surround us that we take simply at face-value that might be more under our control than we may imagine. Elon Musk once stated this as the "branching of probability streams":

"You're going to generate some error between the series of steps you think will occur versus what actually does occur and you want to try to minimize the error. That's a way that I think about it. And I also think about it in terms of probability streams. There's a certain set of probabilities associated with certain outcomes and you want to make sure that you're always the house. So things won't always occur the way you think they'll occur, but if you calculate it out correctly over a series of decisions you will come out significantly ahead."

In some domains, the initial conditions largely determine the outcome, while in others, the launch or flight conditions have outsized impact. But when we assess the probability of certain events or outcomes, we often make assumptions on the nature of the variables involved in these calculations. Yes, many values are fixed, but not as many as we would think. I think we can rig many of the coin tosses in our life.

(I'm not a statistician so if any of this is wrong, please let me know.)

From Ricky Yean's Privilege and Inequality in Silicon Valley:

"Then there’s knowing how to manage resources. Being poor makes you suck at using money as a resource. My time was always cheaper growing up, so I’d rather spend time than spend money."

Everything has a tradeoff (in economic terms, everything has an "opportunity cost," but I really don't like that phrase, so I won't use it).

Shockingly, this actually means that everything has a tradeoff. 

Going to college has a significant tradeoff that is definitely worth considering. Same with graduate school, or marriage, or "career"-ing, or even the language you choose to speak. The people you hang out with. How you spend your Sunday afternoons.

That isn't to say that you should commence ripping your hair out and second-guessing all of your life's decisions. But it's worth noting that, in a world of infinite tradeoffs, you need to be somewhat aware of what you are trading off, as well as which mental models are guiding you to pick a particular batch of tradeoffs over another.

(This was a fun/scary exercise for me because I quickly realized many of my decisions in the past prioritized cocktail-party "You're an impressive young man" over things that I actually found interesting.)

Often, this game of tradeoffs plays out as a battle between time and money: choosing to spend time on something vs. choosing to spend money on it. I know the two aren't mutually exclusive, but for the sake of discussion, we can assume that we're choosing one at the expense of the other.

The Macro Question: Having Time v. Having Money

Time is your most valuable resource. Money buys time. But at what cost? And when is that cost justified?

A working-class single mother of two and a C-suite executive might be just as busy as each other. But the difference is that certain things can be "automated" by the latter through money that might not be automated by the former. Why wait for a train when you can Uber? Why do laundry or clean your apartment or wipe your own ass when you can pay someone to do it for you? The exec effectively buys time to do other things through avoiding subway delays or hour-long dryer cycles. (This is not always a good thing.)

Time availability & the ability to trade in cash for more time is what seems to be what defines wealth. You can be money rich and time poor. You can have a lot of money but still be unwealthy. Perhaps because you're not very good at the cash-for-time business.

In other words, imagine a 2x2 diagram with Having Time and Having Money as axes:

There are several ways you can be poor.

Time poor, money poor.
Time rich, money poor.
Time poor, money rich.
Time rich, money rich.

This is just a very broad-brushed understanding of "poverty"- it exists on two axes. And it is why we might enjoy watching The Wire as much as watching Gossip Girl - both shows describe time-poor environments with starkly different locations on the money axis. It's also an interesting way to understand needs and desires. Your existential needs differ depending on which quadrant you land in. A question for another day might be: do these quadrants have any morality (is it better to be in one quadrant than the other)?

But back to the issue of tradeoffs.

Spending Time vs. Spending Money

Let's weigh the tradeoffs when you decide to spend money on something instead of time. 

Pros: you buy time to focus on other things
Cons: you might be losing a substantial depth of experience

When you have all the time in the world , you invest in certain experiences and habits by spending time on them. This includes figuring things out slowly and painfully over time on your own. 

When you feel you don't have as much time, you skip the discovery trial & error part. To compress the time required to do something, for the sake of urgency and structure (and comfort/certainty), money automates away the stressful, time-consuming parts.

Buying time with money is a great strategy if you know the potential downsides of doing so. But if people trading money for time aren't aware of the tradeoffs between the two, they may easily become blind to the downsides of money vs. time. As humans, we learn best through experience, and passing around pieces of paper can't quite compete with that.

However, if you are constantly re-evaluating what you might be overlooking, then you'll be in a good spot to recognize when it's time to invest time and when it's time to buy time. Tradeoffs are almost always not evenly weighted, so knowing what you're getting yourself into has large implications on the next set of tradeoffs you might face.

Why is this important anyways? Your micro-level, day-to-day decisions on how to spend (time v. money) very quickly accumulate into macro-level, stable holding patterns in what you have (the 2x2 diagram above). 

Much thanks to Dilip Rajan for raising some awesome points of clarification. I've updated the post to include them.

(It's been a while since I've posted anything. But now I'm back to writing regularly, which feels great.)

From John Berger's Way of Seeing:

“One might simplify this by saying: men act and women appear. Men look at women. Women watch themselves being looked at. This determines not only most relations between men and women but also the relation of women to themselves. The surveyor of woman in herself is male: the surveyed female. Thus she turns herself into an object -- and most particularly an object of vision: a sight.”

When you are a white, heterosexual male, chances are you don't walk around feeling like you're being watched, observed, or looked at. When you look in the mirror, you see some approximation of yourself. This freedom frees the white, heterosexual male to observe the world without fearing it. Of course, there are exceptions, but this appears to be the default.

When you are a woman, or brown, or gay, there's a different dynamic at play.

You look in the mirror, and you don't just see yourself. You see something to be beholden. You are primarily an object of someone else's vision.

How does this happen? It starts the first time you walk through an airport security check and realize you're being treated differently than others. It starts when you and your friends are going out in the city and get catcalled and followed by a group of men. It starts with one cop pulling you over for a rolling stop at a stop sign, or a loved one looking at you weird for how you dress, or an epithet screamed out of the window of a passing vehicle.

So when you look in the mirror, you aren't even gazing at yourself with your own eyes. It's a bit dissociative where your gaze becomes the gaze of the person who will be looking at you.

The strange thing that happens is that, over time, you may begin to similarly objectify anyone who looks like you. When you see your own "kind", you instinctively objectify because that's what you do to yourself. It creates this weird self-limiting behavior at the scale of entire communities - blacks/browns/women all judging the hell out of each other silently and then feeling judged silently by their own. It's why we see our own "kind" giving us side-eye, but then we realize we're very unconsciously doing the same thing to them. And if we aren't careful with our sense of self, we very naturally conform or force others to conform to a narrow set of expectations.

Meanwhile, observe a random white dude walking by on the street- he has the freedom to blend into the background. He isn't regularly the object of anyone's constant eye, especially not yours, and so you can choose to see or not see him, it won't matter much to him. (Of course, this dynamic flips to some degree when the same white dude finds himself in Japan or in Zambia.)

When you're so conditioned to the feeling of being looked at, you change the way you behave, and you change the way you view yourself. This all happens so subconsciously that either you're actively fighting/overcoming it, or you're passively succumbing to it. 

From Kevin Simler's essay Wealth: The Toxic Byproduct:

"[...] money spent on consumption is toxic — value-destroying. This is true even in our daily lives, without the literal magic window. Every time we spend money on a yacht or an iPhone or a nice jacket or even food, we're taking something of value from society and using it for our own purposes [...]

As long as someone's money is tucked away in his bank account, we're safe. But the minute it starts to leak out, via consumption, we all become that much worse off [...]

Earning money (via production) is good for others. Spending it (via consumption) is bad."

"A reinforcer is anything that, occurring in conjunction with an act, tends to increase the probability that the act will occur again."

From Jan Gehl's Life Between Buildings:

"When outdoor areas are of poor quality, only strictly necessary activities occur.

When outdoor areas are of high quality, necessary activities take place with approximately the same frequency -- though they clearly tend to take a longer time, because the physical conditions are better. In addition, however, a wide range of optional activities will also occur because place and situation now invite people to stop, sit, eat, play, and so on.

In streets and city spaces of poor quality, only the bare minimum of activity takes place. People hurry home.

In a good environment, a completely different, broad spectrum of human activities is possible."

• The organization as a plant

• The city as a plant

• The child as a plant

• Technology as a plant

• The world as a fractal series of plants watering plants watering plants, and so on.

From Elizabeth Andoh's Kansha: Celebrating Japan's Vegan and Vegetarian Traditions:

"When I bemoaned the need to wait a full year before indulging in [certain foods] again, a Japanese friend taught me three words: hashiri, shun, and nagori.

"Hashiri are those eagerly awaited foods you finally find at market: the early spring peas, small and tender ... or autumn's first wild mushrooms that hint of the woods."

"Shun describes that magic moment when a food is at its peak of flavor and abundant. It is biting into a sugary-sweet corn, bought from a roadside stand on a blazing hot summer's day."

"Nagori is culinary regret ... buying eggplant one more time, late in autumn, knowing they can't be as tasty as the ones stewed with young ginger during the summer rains."

From investor Howard Marks:

"The correctness of a decision can’t be judged from the outcome. Nevertheless, that's how people assess it. A good decision is one that’s optimal at the time it’s made, when the future is by definition unknown. Thus, correct decisions are often unsuccessful, and vice versa.” 

"First-level thinking says, 'It's a good company; let's buy the stock.' Second-level thinking says, 'It's a good company, but everyone thinks it's a great company, and it's not. So the stock's overrated and overpriced; let's sell."

"First-level thinking is simplistic and superficial, and just about everyone can do it (a bad sign for anything involving an attempt at superiority. [...] Second-level thinking is deep, complex and convoluted."

"[...] The bottom line is that first-level thinkers see what's on the surface, react to it simplistically, and buy or sell on the basis of their reactions."

From investor Paul Graham:

"Keep your identity small.

[...] If people can't think clearly about anything that has become part of their identity, then all other things being equal, the best plan is to let as few things into your identity as possible. [...]

Most people reading this will already be fairly tolerant. But there is a step beyond thinking of yourself as x but tolerating y: not even to consider yourself an x. The more labels you have for yourself, the dumber they make you."

There's a small list of thinkers whom I pay especially close attention to. These people include: Michael Lewis, Malcolm Gladwell, Nassim Taleb, Paul Graham, Ta-Nehisi Coates, Kendrick Lamar, and a few more.

Venkatesh Rao is also on this list. He recently shared via social media a great African proverb:

"If you want to go fast, go alone. If you want to go far, go together."

• Dealing with powerful, deep-pocketed people who don't want the idea to succeed.
• Responding to cycle-determined media coverage (they'll love you, then hate you, then love you).
• Creating space for more people to join without overly diluting.
• Maintaining the heart and soul of the movement.
• Letting the movement flourish in the absence of the founder.
• Avoiding too much internal politicking and turmoil.

From Daniel Coyle's The Talent Code:

"The sweet spot: that productive, uncomfortable terrain located just beyond our current abilities, where our reach exceeds our grasp. Deep practice is not simply about struggling; it's about seeking a particular struggle, which involves a cycle of distinct actions."

1. Aim big and audacious
   
   I think people (myself included) get scared of aiming ridiculously high. We overvalue our current selves but undervalue our potential future selves. So what happens is that we set goals that are high, but within arms reach.
   
   And when things are within arms reach, we might not be hellbent enough on attaining them. Whereas if our goals are absurd, we have to re-evaluate whether we really want to achieve them, and if we do, then we get serious. If not, then that's fine-- time to find something you are willing to go pie-in-the-sky for.
   
   
2. Long-term strategy beats short-term optimizations
   
   The LSAT has three sections: logic games, logical reasoning, and reading comprehension.
   
   The logic games section can be mastered in a few short weeks with the right suite of tactics and tricks. Many people spend way too much time working on this section.
   
   The logical reasoning and reading comprehension sections are a bitch. They are mentally draining and they require an intense level of focus, concentration, and skill. To master these sections, you can't just stumble into a silver-bullet tactic. You need a long-term strategy (reading science journals, retaking old sections in loud coffee shops, etc). Performance on these sections often differentiate the average test-taker from the top 20%, and the top 20% from the top 1%.
   
   
3. Obsession with metrics/data often leads to shortcuts
   
   There's a saying that goes like this: "When a measure becomes a target, it ceases to be a good measure." I grew so obsessed with my score that, during early practice tests, I would flip to the back and double-check my answers. This obviously inflated my scores artificially. Bad.
   
   
4. Hoping for a fluke is a recipe for deep disappointment
   
   "Well, let's see how it goes. I might have a good day today." Said no elite performer ever. There's a high degree of determinism whenever you see masters do what they do. The Jordans of the world don't rely on having a lucky day.
   
   
5. Before simplicity, things get complicated
   
   During my time studying for the LSAT, I eventually hit a giant wall. For about 2 months, no matter how hard I tried to figure out what the problem was, my scores weren't improving. I kept exhaustive and detailed track of the type of questions I was struggling with, desperately trying to find a pattern somewhere in there. Things got messy, complicated, frustrating. And then it slowly started clicking and making more sense. I had to wade through immense complexity to get to simple.

This post might only be helpful to people who are studying for the LSAT soon. Whatever.

From David Heinemeier Hansson aka DHH's talk at Stanford, Unlearn Your MBA:

"I have a funny example of how bad things can go when your brain has become all mushy with all this MBA bullshit.

This is Domino's CEO David Brandon talking a few weeks ago:

'The weakness in our value chain with the customer was really in our core product.'

...What?? What does that even mean? Well, I tried to translate that into human, and what I came up with was:

'Let's be honest, our pizza used to suck. I'm sorry. I swear the new ones will be better.'"

From Christopher Alexander’s The Timeless Way of Building:

“Each one of us has, somewhere in his heart, the dream to make a living world, a universe.”

Roman Mars produces an amazing radio show called 99% Invisible. I think there’ve only been a few episodes I haven’t been fully enthralled by.

There’s a theme that recurs (purposefully or accidentally) in his podcasts. These are stories of the human response to architecture that man has designed.

Crammed flop houses in the Bowery neighborhood of NYC.
Questions about tables and chairs (why are tables so low? why are chairs so perpendicular?).
Ugly buildings on college campuses (ironically many of which house architecture programs).

I listen to these podcasts as I walk around NYC’s East Village; I spot the hulking Lower East Side projects that Roman talks about.

Or after the episode on street width, I really do wonder: “Does the combination of narrow streets and tall buildings make me unhappy?”

Lately, 99% Invisible spurred another thought that I can’t seem to unthink. Why are our cities so concrete? What does that say about our relationship with our world?

Many of the things I see in NYC are awe-inspiring when looked at in isolation. But taken together with everything else, there seems to be a dullness, a drabness, that remains, regardless of how vibrant and noisy and lively the streets are during brunch time.

There’s so much damn concrete. It’s as if we designed our cities to escape the natural world. Trees, grass, critters, parks — these are mere amenities confined to neatly packaged squares. 

Occasionally, this makes us overtly antsy. So we go to the beach with some friends to unwind and take in the calming, intimidating beauty of the world. Then we complain about bug bites.

The concrete that surrounds us has probably developed a toxic relationship between us and the world. Instead of trying to harness nature so that we and it can coexist, we suppress it and, in its stead, try to approximate it with our toys.

Replace wood with concrete, gravel and sand with pavement.

It’s seems lazy! What if instead of concrete, we had streets dominated by trees; roads and sidewalks that crunched naturally under our feet; filtration systems that weren’t just a series of underground pipes?

I think we’d be a happier lot. Our innovations would look much different, maybe even better than what we see now.

I say all this to try to shake off my own city-induced neuroticism. I'm a (slowly) aspiring hippie.