a guide to recognizing bullshit

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."

Game of Thrones, British Accents, and Bullshit

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 DisruptedThe 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."

When a ritual, just like notation or jargon, exists theatrically rather than functionally, then we know there's a problem. 

The Effect of Permitting Bullshit

During a brief stint working with a PR firm in NYC and a year-plus with a media startup, I've learned that the cream rarely rises to the top. The cream is largely manufactured.

The people running sexy companies, getting frequent mentions in influential publications, and shepherding large Twitter followings -- many of them got to that position by strategically using some mix of notational/linguistic/ritualistic bullshit to convince people that they know what they are doing. They were able to sell themselves as authorities.

And because the real authorities were too busy checking their own work to properly sculpt their "brand", these pseudo-authorities now drive mainstream thinking on most things.

However, not all prominent thinkers and doers are bullshitters. It's our job as consumers to learn how to tell the difference.

a personal grad school year, 3 months in

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."

From David Graeber's On the Phenomenon of Bullshit Jobs:
" [...]  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."
From Nassim Taleb's How to Legally Own Another Person:
"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 Johan Huizinga's Homo Ludens: A Study of the Play-Element in Culture:
"Our point of departure must be the conception of an almost childlike play-sense expressing itself in various play-forms, some serious, some playful, but all rooted in ritual and productive of culture by allowing the innate human need of rhythm, harmony, change, alternation, contrast and climax, etc., to unfold in full richness."
A couple months ago, I left my job to pursue personal projects until I ran out of money (that's probably just code for "I wanted my own schedule"). On the surface, the decision seemed risky; to me, it was as risk averse as anything I've ever done.

I had grown increasingly aware of a trend amongst myself and my friends. College had made us well-groomed analysts -- give us a research task, dangle us some $$ + perks + prestige, and we'll produce the best fucking slide deck or Excel workbook you'll ever see.

The lucky few of us who had spent college aggressively seeking and cultivating their interests scoff at our situation. The rest of us, in the absence of any clear interest in anything except status and validation, decided to go into financial/professional/technical services hoping to acquire some "Skills" that would later be great "leverage" when we finally do decide to "do what we love" (which we haven't spent enough time learning about, so...).

That is scary. I grew up writing and enacting really bizarre mini-plays with my siblings; singing in the shower and then translating those half-baked melodies into half-baked Garage Band songs; reading Orioles box scores, memorizing player stats and then predicting what their final season stats would look like. The things we did when no one forced us to do them. I'm definitely not alone here, though the specifics may vary.

Personal Grad School, 3 Months In

Anyways, it's been three months since I made my decision to leave my software engineering job. My goals for "personal grad school" are, broadly, to be able to quickly build anything from the ground up in a really short period of time, regardless of medium or difficulty. There were successes and hiccups and huge failures. I will document them below as honestly as possible.

Starting a startup: Failure

This was rather interesting. To convince myself and others that quitting my job was a good idea, I grabbed my biggest hammer and started looking for nails. And so everything in the process looked like a nail. Translation: I jumped into something to "play entrepreneur" and not actually build anything.

I spent two months talking to current and former teachers, school administrators, principals, parents, students, investors, other entrepreneurs. I tried to convince a great friend to leave his job at Uber to join me (so douchey of me). I applied to Y Combinator for funding for a nonexistent product that had one founder (me), getting mentors to vouch for my application. I wrote some code and spent too much time trying to make it perfect. I hung out at WeWork because that felt pretty cool.

This fizzled out pretty terribly. I had nothing delivered, no pre-sales; I hadn't even validated the idea. I was running around trying to convince people my idea was awesome and totally worth investing $$ in. I was scared, so I just did things that looked like success; this was my old brain still at work. But I learned a lot about myself during these two months. The epic failure was totally worth it.

Diving into technical concepts: Success

I realized from my failures that I didn't have enough confidence in my engineering, design, and sales skills to do anything. So the following month, I devoted each week to an intense, project-based exploration of technical concepts. Each week, I had to deliver a product and a blog post walking through what I built. During this month, I learned how to (and now ensues some largely unintelligible technical jargon): deploy a load balanced app to AWS, incorporate a fully Dockerized development-to-deployment workflow, write a simple virtual stack machine in Java, learn functional programming and math fundamentals via the Haskell programming language, and use bit manipulation and Hamming distance to crack repeated-XOR-encrypted messages in Node and Python.

(Edit: Also important note here is that I started learning how to code a little under 2 years ago. Discussion for another day: strangely, we overvalue our short-term selves and undervalue our slightly less short-term selves.)

There's a common piece of wisdom that goes like "The antidote to fear is hustle." To integrate that idea into constantly working on things that I knew nothing about, I broke each week into three 2-day sprints. Every 48 hours, I needed to be able to tangibly do a new thing. By doing this, I would force myself to focus only on what was vital and only go down rabbit holes that were necessary. Hat tip to Hack Reactor for teaching me this technique.

Building shit fast: Success (and ongoing)

Finally, it was time to get to start getting things out the door. My confidence in my coding skills had risen tremendously in just a short month. I have a Google Doc of around 500 small seeds of ideas, so I began picking a few to work on. In one month's time, I built: a Chrome new tab extension called "Do One Thing" (a to-do list capped at just one thing every day); a Slack bot called "Hack Genie" (who answers your code questions for you); and a book recommendations list called "Bookswell".

Each of these had varying levels of success. The Chrome extension took one day to write, but it didn't appear to be something many more people would find uniquely interesting, so I moved onto my next project (though I still use this extension every day). The Slack bot also took one day, and I still use it fairly often, but it also wasn't something that I felt many people would fall in love with.

Bookswell project was pretty awesome. Before writing any code, I simply shared a book recommendations spreadsheet that I had been passively working on for a year. The response was overwhelming, so I spent a few weeks building a web version of it, which itself has gotten thousands of visits in just a week or so of being live. My next steps with this are to just get it more exposure.

The cool part with each of these projects was that the only calculation running in my head was whether they were immensely useful or not. I wasn't worried about whether I had the chops to get them done or not, because the previous month had ingrained in me that I could now build almost anything I wanted to. 

Most importantly, I wasn't evaluating projects based on "What will this lead to?" or "What's the long-term vision?" (This required some pretty intense unlearning of old habits.) It's this type of thinking that squashes seeds before they have time to bloom. Many amazing things arrive in this world ugly, slightly deformed, and with no clear sign of why they made it that far. Despite all that, they managed to make themselves useful, for reasons yet unclear to their makers. 

Projects moving forward (update: December 3, 2016)

Given the sprawled shape of this calendar year, I ended up further sprawling. My mentors Myles and Oz invited me to join them in SF for ~10 weeks to eat/breathe/sleep computer architecture & operating systems. The amount of learning done here cannot be overstated.

However, my most profound experiences in SF revolved around building a daily practice of meditation, prayer, running, and writing.

I'm now back on the East Coast ready to move from opportunistic maneuvers to more deliberate, principled, craft-driven decisions. Programming is a lot of fun, and it can deliver pretty outsized value to society (in some cases). I'm excited to dig in and focus on this for the upcoming years.

The Secret Sauce

Writing has without a doubt been the secret sauce over the past few months. Every project and every concept that I was struggling with required a blog post of some sort. This forced me to be able to appropriately explain what I had learned. Oftentimes, we say we've learned something when we are able to do it right once, but it is in being able to explain it coherently that the concept finally gets internalized.

Beyond that, writing has helped me organize some of the more esoteric ideas and thoughts I've been having learning about (which is essentially the purpose of this Posthaven blog). I highly recommend that everyone keeps their own personal blogs with this express purpose. The mini-trends in what you choose to write about will teach you more about yourself than almost anything else.

new scarcity in the information age

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."

From investor Peter Thiel's Zero to One:

"Courage is in far shorter supply than genius."

Disclaimer: this post is longer than my usual stuff, and it's still a work in progress. I may have huge blind spots and indulgences here, and I'd love to hear where they are or if you got totally lost somewhere in my rambling mess of an essay. But I had to get my thoughts down, so alas here we are.

In classical economics, there's an idea called the Scarcity Principle. If you've ever taken econ, this is probably one of the first things you learn.

The scarcity principle, in (very slightly) technical terms, is the market disequilibrium caused by the limited supply of a good and a corresponding high demand for it. The efficient markets hypothesis implies that when this happens, either supply expands to meet the demand, or prices go up to lower the demand until supply = demand.

It's arbitrage in the most fundamental sense -- if you as a supplier discover a disequilibrium, you start selling that thing at higher prices. Or you start making more of that thing and undercut your competitors at a lower price. Human Craftiness 101.

Scarcity Principle: Used Bikes and Tuna Fish

An example that comes to mind is the used bicycle market. In any bike-friendly city, you can probably buy a used vintage Trek road bike for $150 off Craigslist, refurbish it for $50-100, and then resell it for ~$450-600 on eBay.

There's an unmet demand for vintage bikes that are in great physical condition. These types of bikes are scarce. Your Craigslist sneakiness happened to respond to that scarcity. And this scarcity will remain as long as hipsters keep riding fresh bikes and as long as refurbishing a busted beauty takes more time and effort than a normal person would want.

In the excellent documentary Jiro Dreams of Sushi, you also see this principle in action: the wholesale price of tuna has risen tremendously as the tuna population has dwindled and the global demand for fatty tuna has increased. 

This has led two a few parallel trends: i) things that look and taste like tuna being labeled and sold as tuna, ii) large corporations running tuna farms, basically breeding and "manufacturing" tuna, and iii) high-end restaurants driving up their prices (knowing their customers are price insensitive), thus continuing to buy wild tuna. 

Tuna is the scarce resource. It will remain scarce as long as its texture and flavor remain highly-valued and as long as the tuna population remains endangered.

Building "Old Scarcity"

Guess what the big reveal is? Our highly-professionalized, white-collar knowledge market is also susceptible to the Scarcity Principle (as are our new media darlings out in Silicon Valley). And that is where this blog post is headed.

Over the past 150 years, the US economy has become highly financialized and instrumentalized. The concepts of corporations, public markets, commodities, derivatives, and stakeholders have been formulated to help us regulate, predict, reason about, and exploit human economic activity at a large scale.

Those who can understand the markets can figure out where the money is flowing and redirect some of it to themselves. Managing this complex system in part created new, lucrative livelihoods -- corporate law, investment banking, management consulting, hedge funds, etc. This is the scarcity principle in action-- Old Scarcity, as I'll call it. If public corporations need to drive value to stakeholders, how? If banks need to drive returns to investors, how?

Consultants provide analyses and recommendations to executives, bankers provide financial models and projections to potential investors, lawyers provide due diligence and legal paperwork to all parties involved. What is scarce here is the know-how of navigating a complex system safely and opportunistically (sounds a lot like driving a car, huh). Since money is exchanging hands in such large sums to make these transactions/deals happen, this know-how gets compensated handsomely. Who benefits? Smart, highly analytical, and hard-working elites.

Here's the thing, though: Old Scarcity is subject to the same forces as fish and used bikes. Old Scarcity remains as long as the system in which it operates remains somewhat understandable and predictable. And Old Scarcity remains as long as there aren't enough people with the know-how to do all of this financial wrangling and navigating well.

Dismantling "Old Scarcity"

Have you heard the old folktale of John Henry? John Henry was a skilled steel-driver who beat a steam-powered hammer in a race to build a railroad tunnel, but ultimately died as his heart gave out due to the stress of the job. 

The common takeaway with this story is the power of human industriousness, but really, all I see is a proud guy who lost to a machine. Maybe he should've derived his self-worth from something a machine couldn't replicate as easily. Maybe this is a moving target and what it means to be human keeps evolving as we make earlier versions of ourselves obsolete.

This is the crossroads at which the Old Scarcity industries find themselves at. On one hand, the system itself is becoming far less predictable and far more complex. On the other hand, trading, document review, and data analysis by algorithms are here, and they are beginning to do a better job than their lawyer/banker/consultant counterparts. The know-how is no longer scarce (or even useful all the time).

It will take several decades for this reality to really permeate and take full hold over the labor market, but it's here. Why pay a bunch of 20-somethings premium salaries when a monthly subscription to PandoraTech will do all of their jobs for you? The previously highly lucrative jobs as glorified wheel-greasers and bean counters will soon be done much faster and better by an algorithm written by your geeky cousin. And so the Scarcity Principle in this professional economy will be largely optimized into efficiency by our machine friends.

Building "New Scarcity"

The demise of Old Scarcity will illuminate the New Scarcity. Information and knowledge used to be scarce, it used to be something that institutions hoarded and justifiably charged $200,000 for. But now (almost) anything can, with enough Google-fu, be learned. Of course, some things still can't, and maybe those things are worth investigating further.

So what is scarce in a world where information is abundant? Courage and taste

The courage to create and build things that have very little precedence, or to create anything at all, is scarce. Machine learning works really well with large datasets, but what if the dataset is empty? On the flip side, when you have so much access to information (and thus many logical reasons to not do something), why do anything that will inevitably draw criticism and doubt? Those who are willing to do things are hot commodities.

Taste (the ability to be opinionated, principled, and insightful about things) is scarce. What use is all this data when it drowns, overwhelms, confuses, contradicts? What have you really learned when your information consumption is just an infinite stream of watered-down clickbait? Can you trust your gut? Those who know how to are hot commodities.

When large-scale computing can do most of our repeatable tasks infinitely faster and (for the most part) better than us, what do we have left to do? Create, build, express, tell stories, do things differently, think deeply and holistically. Either that, or become a computer whisperer and tune those algorithms so that more jobs get obsoleted and more people can be forced to think creatively.

It's less about acquiring knowledge, capital, and labor. Those are cheap and easy now. Those are things a computer can do a lot of this for you. But the things that aren't repeatable and scalable yet are things that require a personal touch. Art, self-expression, and exploration. Through this lens, the sciences and the humanities are more similar than we think.

We're already seeing this happen. Curated lists of things are popping up everywhere (and doing fantastically well). Artsy niche businesses, services, and boutiques are popping up at the grassroots level. Tech companies are focusing more and more on designing strong customer experiences. Lawyers are offloading their grunt work to software so that they can focus on building relationships, understanding the big picture, and catching any details that don't appear in databases yet. Some consulting firms are moving their work towards actually implementing their operational recommendations; others are being hired to ask the right questions, rather than to give the "right" answers.

As the emerging wisdom claims, many jobs will be lost, but a new breed of them will probably be created-- some that we can't quite imagine as being jobs yet. Just as several centuries ago, the job title of "he who pores over a spreadsheet" was unfathomable.

It's an exciting time to be thinking and doing.


how to stop lying to yourself about your career and life, in 7 sloppy graphs

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
2. The Mythical Success Arc

"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
3. Compounding

"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
4. Reference Bias

“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
5. The Location of Your Efforts

"The frequency of correctness does not matter; it is the magnitude of correctness that matters."
More Than You Know, Michael Mauboussin
6. Decision-Making & Skin in the Game

“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

7. What Are Needs?

"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

your three selfs: the artist, the executive, the critic

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'."

I always thought that a singular me was in charge of running (and repeating) the process of making decisions. Any inconsistencies could be explained by shortcomings in me, the unified self. Whenever I felt the strong pangs of discomfort from not having an "n-year life plan", this self would arrive upon a way to exit that discomfort.

I now strongly suspect that the decision-maker isn't a cohesive self, but rather a Kakuist "patchwork of competing and often contradictory tendencies." This is reminiscent of that Pixar movie Inside Out, which models the mind as a merry band of characters named Joy, Sadness, Anger, Fear, and Disgust. I think it's more useful to characterize the mind using more dynamic "character archetypes."

(And now ensues a highly unscientific, very anecdotal, metaphor-driven "analysis.")

The Three Archetypes of the Mind

There's the artist, the inner child whose curiosity drives him to poke/prod/build/break/fix. He creates.
Then there's the executive, the thoughtful driver skilled at steering, deciding, and reacting. He navigates.
Finally there's the critic, the guy who just wants to make sure nothing gets overlooked. He deliberates.

Together, this motley crew can do amazing things. But external stressors and internal insecurities often create imbalances between the three. Over time, each character wields a different level influence on the others. We might call this "personality." We might call it "neurosis."

Stress can to some degree be viewed as the manifestation of the different types of struggle taking place between these three characters.

When the critic is screaming those oh-so-sweet-nothings of self-doubt and unworthiness, it means there's dissonance created by some inability by the artist and the executive to deal with a situation. The artist wants to go one way, but the executive is dragging him in another, or vice versa. The critic is sounding the alarm, but his job isn't to problem-solve; he just knows something is wrong. 

When the executive is overpowering, it looks like an inability to sit still, perhaps caused by some disagreement between the artist and the critic. Maybe the artist wants to express something that the critic doesn't think is a good idea, and the executive doesn't want anything to do with that conversation (even though it might be a useful one). The executive is providing a solution, but he doesn't understand the problem.

When the artist takes complete control, it can be characterized by obsessive, frenetic (and maybe hermetic) tendencies all driven by the desire to create and express. What's the tension here? Perhaps the executive and the critic are having a hissy fit. They can't come to terms on what to do, and so the artist is impatient and decides to throw the proverbial kitchen sink at the problem. The artist doesn't care for solving problems or providing solutions; he just wants to express something core to his being, at the expense of all else. 

Depending on your personality, you may be picking sides already. I know I love the artist and everything he stands for, but I know other people who would side 100% with the executive, and others who think the critic is highly underrated and needs some love, too.

Yet Another Personality Typeset 

All three need to know their role in any given situation. They need to maintain a healthy relationship with each other. That doesn't mean that they all share the load equally. I'd say there are 6 different permutations that arise from a stable-but-hierarchical arrangement between the three characters:

Exploratory Risk-Taking:
  • 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.


a less-annoying way to learn things

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?"

From Tim Gallwey, author of The Inner Game of Tennis:
"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."
In high school, I prided myself on being a "try hard" - maybe this evokes the phrase "high work-rate." The idea was that if I worked really hard at the obvious things, my performance at a given task would improve vastly. These obvious things included: highlighting textbooks, making flashcards, going all-out all the time in soccer practice, trying to out-hustle opponents on the tennis court; generally, anything giving the visual impression that I was putting in more work.

The Song and Dance of Everything

I had an incredible tennis coach and life mentor named Mr. Kong (or just 'Coach'). He tried to teach me not to try so hard, to focus on the right things

But I was stubborn - my existing mode of work had gotten me this far without a hitch, why change things? He'd have me focus on the rhythm of my feet as I moved around the court; the pitch and sound and timbre of the ball hitting the string bed; the depth and speed of the ball as it came over the net; the different ways I could impart spin on the ball, and what effect it would have on the its trajectory and bounce. I didn't listen.

In retrospect, I realize Coach was trying to get me to focus on reframing the problem. The problem as I had viewed it was "How can I get better?" But if I were to inspect the problem as Bernard Roth suggests, I'd ask "What would solving this problem do for me?" I'd get "better" at tennis so that I could play #1 singles, or gain the admiration of people around me. And what would accomplishing these things do for me? It would affirm my place and my value in the world. And what would that do for me? It would help me have a healthier relationship with the world so that I could enjoy it.

Coach wanted me to reframe the problem to that very last one. How can tennis skip over those intermediary "problems" and cut to the chase? How can it be a vessel to building a healthier relationship with the world around me? Treat tennis as a choreographed song-and-dance (learn the moves), rather than the purpose-driven mechanics of a competitive, "If you win, I lose" game. Learn to love things before you try to master them. Mastery will probably come easier that way.

This is a video of a beginner learning to play tennis in 10 minutes. It's amazing. Great quote (from Tim Gallwey himself):

"... So they’re not thinking, Oh this is what he’s doing with his elbow, this is what he’s doing with his hands. They’re not trying to remember all that. They start humming, and they see themselves doing similar things, muscular movements, as I did. They’re not thinking about it, so it comes out naturally and fluidly."

The assumption here is that natural and fluid is good. It requires less conscious thought than it does to constantly remind yourself to bend your knees, turn your shoulders, brush up on contact, hit the ball ahead of you, oh, and all the while, don't think so much.

At tennis clubs around the country, pros are fleecing amateurs for $150/hour lessons just to give this brand of detailed feedback. The amateurs think they're getting their money's worth, even though their game hasn't improved in 2 years. The pros try to justify the high costs by drowning the amateurs with minutiae. The $150 rate ends up compensating the pro for showing off his deep technical knowledge, rather than actually helping someone become a better player.

The Annoying Science of Spaced Repetition

Learning in general often sees this same dichotomy between the conscious and unconscious. For instance, one concept that's made rounds in mainstream media is the idea of "spaced repetition." To paraphrase the idea: the way to learn something and get something to stick is to review the concept at regular intervals. To make it seem more scientific, let's introduce a graph:
This is fantastic. The solution to learning more effectively is to, at regular intervals, review things you just recently learned. So you'll see a lot of tactics/methods out there in which you keep a really detailed spreadsheet telling you to very mechanically track the things you apparently learned, and then to, every Tuesday morning before your mason jar full of breakfast Soylent (yum), review said concepts.

This spreadsheet-driven approach works for a particular type of person -- namely, those whose process-oriented nature outweighs their self-doubt and fear of failure. These types of people have already developed the habits required to learn at a very high level.

But how about the rest of us, though? We're just getting our feet wet, and the experts want us to use world-class tactics on day one. This is an easy failure pattern. 

But like tennis, the problem of "learning things faster and better" is a matter of reframing the problem to first "learn to love the things you want to master."

For instance.

Fear of reading books:

I've noticed a lot of people don't get into the habit of reading books because they're afraid to not finish them. This is an example of having a strange mental model of what "good reading" looks like - namely, that to read a new book, you need to read another book cover to cover. Or that, to read books, you need to grab something profound and dense and incomprehensible. 

But if you're just getting into the reading game, I suggest keeping a rotating shelf of books (perhaps on your Kindle). You read what you're in the mood for. Skip around, abandon books, find new ones. If what you're reading is too dense, find a less dense treatment of the same topic. "Dense material" is just code for needing to read the prerequisites (idea borrowed from Scott Young). If the prerequisites aren't fun or engaging, find something that will keep your attention. Soon enough, you'll pay more attention to the fact that you finished 50 books this year rather than the fact that you abandoned 200. That's probably 50 more than your total from the past 5 years combined.

The amazing thing about this tactic is that it ends up approximating "spaced repetition" without even trying. You'll start noticing that the concepts in your rotating bookshelf are actually pretty closely related. You'll find yourself reading a chapter of The Hunger Games and a passage will remind you of what you read last week in a book on neuroplasticity. And so now that concept is forever etched in your memory.

Once reading becomes integral to life, then you start a conscious spaced-repetition practice. But to attempt mastery before enjoyment is what they say "putting the cart before the horse."


the need for a new American Dream

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."
The American Dream often looks like a cushy job, a big house, a white fence, a yard, and the soothing chirps of some happily nested family of neighborhood birds.

At any given moment, millions pursue this dream the best they can. It often begins in poverty. A family seeking a better quality of life observes what they have and realizes that something about it just isn't right. A child becomes a vessel to a better life, via good grades, diplomas, and paychecks. This is great.

We see this happening generation to generation, as the once-impoverished are now leading (what appears to be) happy, comfortable lives.

The Inheritance of Meaning

For most people, going through this entire process takes several decades, and by the time the process is complete, they're probably deep into the universe of devoting themselves to the well-being of their children. From the looks of it, it worked. And it's all they've ever known; they'll most likely pass it down to their kids as well.

Thus a formula for living is derived to solve for the pesky question of meaning. Go to school, get the best grades, join the best institutions, and get the best jobs. This works for a short while.

But that pesky little question of meaning was never precisely defined-- what is meaning and purpose? Is it monolithic? Are your parents' estimations of meaning the same as yours? How should one live to engage with the question in a healthy manner? Over the past millennium, daily life for humans has radically changed, but the same fundamental questions remain (as evidence, flip through A History of Private Life: From Pagan Rome to Byzantium)

At some point in the American Dream journey, meaning morphs from "put food on the table for the family" to something entirely different. This inconvenient truth gets lost in between Math Bowl competitions, orchestra auditions, and SAT prep courses. So everyone is left fighting yesterday's wars -- "meaning" doesn't evolve with the arrival of new conditions. The privileged children of the new elite end up competing over the same things, without the same set of motivating impulses guiding them down these pathways.

One Man's Meaning Is Another Man's Crisis

Countless highly educated kids, cut from this American Dream cloth, graduate from college every year as near clones of each other. They've all just about gotten the same grades, interned at the same tier of companies, participated in roughly the same types of "extracurriculars", and applied to the same schools and jobs. They never did anything without unconsciously running a calculation in their head of how that fits in with their "paper" self. I know because I'm one of them.

In the words of former Yale professor William Dereciewicz, these young elites graduated as "excellent sheep." Never having had to deal with any form of uncertainty, they continually do what is expected of them, and they do it damn well. In the back of our mind, maybe after a 3rd year doing the same humdrum work at a big consulting firm (or these days, a sexy, well-funded tech startup), just maybe we'll wonder why we're doing this.

But our brains have calcified to be unable to imagine a life outside of what everyone views as success. Even though, now more than ever, one can find fulfillment in almost any category of creative work.

I still struggle with all this. You can't rewire 20+ years of training overnight. And you can't rewire thousands of years of evolutionary reinforcement telling me to avoid uncertainty.

A common frame of re-imagination I've found is to seek out people who, coming from a position of some sliver of privilege, decided to go off-script. (Important to note that "off-script" can take the form of different things to different people. This list takes a specific form of off-script):
  • 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.

the three reactions to kool-aid

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.


how to game a fair coin

From Jean-Paul Sartre:

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

Statistics 101

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.)


the tradeoff between time and money

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.