Ammar Mian

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.